Bile alcohol glucuronides: regioselective O-glucuronidation of 5β-cholestane-3α,7α,12α,25-tetrol and 24-nor-5β-cholestane-3α,7α,12α,25-tetrol
A facile and regiocontrolled procedure for the preparation of 5β-cholestane-3α,7α,12α,25-tetrol-3-O-β-d-glucuronide and its corresponding C-26 analogue is described. The method involves direct coupling of bile alcohols, namely, 5β-cholestane-3α,7α,12α-25-tetrol and 24-nor-5β-cholestane-3α,7α,12α,25-...
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| Format: |
E-Artikel |
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| Sprache: |
Englisch |
| Erschienen: |
1993 |
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| Reproduktion: |
Elsevier Journal Backfiles on ScienceDirect 1907 - 2002 |
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| Übergeordnetes Werk: |
in: Carbohydrate Research - Amsterdam : Elsevier, 240(1993), Seite 133-142 |
| Übergeordnetes Werk: |
volume:240 ; year:1993 ; pages:133-142 |
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| 245 | 1 | 0 | |a Bile alcohol glucuronides: regioselective O-glucuronidation of 5β-cholestane-3α,7α,12α,25-tetrol and 24-nor-5β-cholestane-3α,7α,12α,25-tetrol |
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| 520 | |a A facile and regiocontrolled procedure for the preparation of 5β-cholestane-3α,7α,12α,25-tetrol-3-O-β-d-glucuronide and its corresponding C-26 analogue is described. The method involves direct coupling of bile alcohols, namely, 5β-cholestane-3α,7α,12α-25-tetrol and 24-nor-5β-cholestane-3α,7α,12α,25-tetrol to methyl (tetra-O-acetyl-β-d-glucopyranuronate) in the presence of a Lewis acid, tin(IV) chloride, in dichloromethane. The resulting anomeric pairs of 1,2-trans- and 1,2-cis-glucuronides of tetrols were resolved by analytical and preparative thin-layer chromatography, and their identities were established by high-resolution ^1H NMR spectroscopy and by chemical-ionization and fast-atom-bombardment mass spectrometry. The method described has a practical advantage over the traditional two-step synthesis involving bromides as it is more efficient and uses inexpensive and less toxic materials. It is suggested that these compounds will be useful for studying permeability of the blood-brain barrier in cerebrotendinous xanthomatosis (CTX). | ||
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| 700 | 1 | |a Williams, T.H. |4 oth | |
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(DE-627)NLEJ175503869 (DE-599)GBVNLZ175503869 DE-627 ger DE-627 rakwb eng Bile alcohol glucuronides: regioselective O-glucuronidation of 5β-cholestane-3α,7α,12α,25-tetrol and 24-nor-5β-cholestane-3α,7α,12α,25-tetrol 1993 nicht spezifiziert zzz rdacontent nicht spezifiziert z rdamedia nicht spezifiziert zu rdacarrier A facile and regiocontrolled procedure for the preparation of 5β-cholestane-3α,7α,12α,25-tetrol-3-O-β-d-glucuronide and its corresponding C-26 analogue is described. The method involves direct coupling of bile alcohols, namely, 5β-cholestane-3α,7α,12α-25-tetrol and 24-nor-5β-cholestane-3α,7α,12α,25-tetrol to methyl (tetra-O-acetyl-β-d-glucopyranuronate) in the presence of a Lewis acid, tin(IV) chloride, in dichloromethane. The resulting anomeric pairs of 1,2-trans- and 1,2-cis-glucuronides of tetrols were resolved by analytical and preparative thin-layer chromatography, and their identities were established by high-resolution ^1H NMR spectroscopy and by chemical-ionization and fast-atom-bombardment mass spectrometry. The method described has a practical advantage over the traditional two-step synthesis involving bromides as it is more efficient and uses inexpensive and less toxic materials. It is suggested that these compounds will be useful for studying permeability of the blood-brain barrier in cerebrotendinous xanthomatosis (CTX). Elsevier Journal Backfiles on ScienceDirect 1907 - 2002 Dayal, B. oth Salen, G. oth Padia, J. oth Shefer, S. oth Tint, G.S. oth Sasso, G. oth Williams, T.H. oth in Carbohydrate Research Amsterdam : Elsevier 240(1993), Seite 133-142 (DE-627)NLEJ175413258 (DE-600)1496822-8 0008-6215 nnns volume:240 year:1993 pages:133-142 http://linkinghub.elsevier.com/retrieve/pii/0008-6215(93)84178-9 GBV_USEFLAG_H ZDB-1-SDJ GBV_NL_ARTICLE AR 240 1993 133-142 |
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(DE-627)NLEJ175503869 (DE-599)GBVNLZ175503869 DE-627 ger DE-627 rakwb eng Bile alcohol glucuronides: regioselective O-glucuronidation of 5β-cholestane-3α,7α,12α,25-tetrol and 24-nor-5β-cholestane-3α,7α,12α,25-tetrol 1993 nicht spezifiziert zzz rdacontent nicht spezifiziert z rdamedia nicht spezifiziert zu rdacarrier A facile and regiocontrolled procedure for the preparation of 5β-cholestane-3α,7α,12α,25-tetrol-3-O-β-d-glucuronide and its corresponding C-26 analogue is described. The method involves direct coupling of bile alcohols, namely, 5β-cholestane-3α,7α,12α-25-tetrol and 24-nor-5β-cholestane-3α,7α,12α,25-tetrol to methyl (tetra-O-acetyl-β-d-glucopyranuronate) in the presence of a Lewis acid, tin(IV) chloride, in dichloromethane. The resulting anomeric pairs of 1,2-trans- and 1,2-cis-glucuronides of tetrols were resolved by analytical and preparative thin-layer chromatography, and their identities were established by high-resolution ^1H NMR spectroscopy and by chemical-ionization and fast-atom-bombardment mass spectrometry. The method described has a practical advantage over the traditional two-step synthesis involving bromides as it is more efficient and uses inexpensive and less toxic materials. It is suggested that these compounds will be useful for studying permeability of the blood-brain barrier in cerebrotendinous xanthomatosis (CTX). Elsevier Journal Backfiles on ScienceDirect 1907 - 2002 Dayal, B. oth Salen, G. oth Padia, J. oth Shefer, S. oth Tint, G.S. oth Sasso, G. oth Williams, T.H. oth in Carbohydrate Research Amsterdam : Elsevier 240(1993), Seite 133-142 (DE-627)NLEJ175413258 (DE-600)1496822-8 0008-6215 nnns volume:240 year:1993 pages:133-142 http://linkinghub.elsevier.com/retrieve/pii/0008-6215(93)84178-9 GBV_USEFLAG_H ZDB-1-SDJ GBV_NL_ARTICLE AR 240 1993 133-142 |
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(DE-627)NLEJ175503869 (DE-599)GBVNLZ175503869 DE-627 ger DE-627 rakwb eng Bile alcohol glucuronides: regioselective O-glucuronidation of 5β-cholestane-3α,7α,12α,25-tetrol and 24-nor-5β-cholestane-3α,7α,12α,25-tetrol 1993 nicht spezifiziert zzz rdacontent nicht spezifiziert z rdamedia nicht spezifiziert zu rdacarrier A facile and regiocontrolled procedure for the preparation of 5β-cholestane-3α,7α,12α,25-tetrol-3-O-β-d-glucuronide and its corresponding C-26 analogue is described. The method involves direct coupling of bile alcohols, namely, 5β-cholestane-3α,7α,12α-25-tetrol and 24-nor-5β-cholestane-3α,7α,12α,25-tetrol to methyl (tetra-O-acetyl-β-d-glucopyranuronate) in the presence of a Lewis acid, tin(IV) chloride, in dichloromethane. The resulting anomeric pairs of 1,2-trans- and 1,2-cis-glucuronides of tetrols were resolved by analytical and preparative thin-layer chromatography, and their identities were established by high-resolution ^1H NMR spectroscopy and by chemical-ionization and fast-atom-bombardment mass spectrometry. The method described has a practical advantage over the traditional two-step synthesis involving bromides as it is more efficient and uses inexpensive and less toxic materials. It is suggested that these compounds will be useful for studying permeability of the blood-brain barrier in cerebrotendinous xanthomatosis (CTX). Elsevier Journal Backfiles on ScienceDirect 1907 - 2002 Dayal, B. oth Salen, G. oth Padia, J. oth Shefer, S. oth Tint, G.S. oth Sasso, G. oth Williams, T.H. oth in Carbohydrate Research Amsterdam : Elsevier 240(1993), Seite 133-142 (DE-627)NLEJ175413258 (DE-600)1496822-8 0008-6215 nnns volume:240 year:1993 pages:133-142 http://linkinghub.elsevier.com/retrieve/pii/0008-6215(93)84178-9 GBV_USEFLAG_H ZDB-1-SDJ GBV_NL_ARTICLE AR 240 1993 133-142 |
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(DE-627)NLEJ175503869 (DE-599)GBVNLZ175503869 DE-627 ger DE-627 rakwb eng Bile alcohol glucuronides: regioselective O-glucuronidation of 5β-cholestane-3α,7α,12α,25-tetrol and 24-nor-5β-cholestane-3α,7α,12α,25-tetrol 1993 nicht spezifiziert zzz rdacontent nicht spezifiziert z rdamedia nicht spezifiziert zu rdacarrier A facile and regiocontrolled procedure for the preparation of 5β-cholestane-3α,7α,12α,25-tetrol-3-O-β-d-glucuronide and its corresponding C-26 analogue is described. The method involves direct coupling of bile alcohols, namely, 5β-cholestane-3α,7α,12α-25-tetrol and 24-nor-5β-cholestane-3α,7α,12α,25-tetrol to methyl (tetra-O-acetyl-β-d-glucopyranuronate) in the presence of a Lewis acid, tin(IV) chloride, in dichloromethane. The resulting anomeric pairs of 1,2-trans- and 1,2-cis-glucuronides of tetrols were resolved by analytical and preparative thin-layer chromatography, and their identities were established by high-resolution ^1H NMR spectroscopy and by chemical-ionization and fast-atom-bombardment mass spectrometry. The method described has a practical advantage over the traditional two-step synthesis involving bromides as it is more efficient and uses inexpensive and less toxic materials. It is suggested that these compounds will be useful for studying permeability of the blood-brain barrier in cerebrotendinous xanthomatosis (CTX). Elsevier Journal Backfiles on ScienceDirect 1907 - 2002 Dayal, B. oth Salen, G. oth Padia, J. oth Shefer, S. oth Tint, G.S. oth Sasso, G. oth Williams, T.H. oth in Carbohydrate Research Amsterdam : Elsevier 240(1993), Seite 133-142 (DE-627)NLEJ175413258 (DE-600)1496822-8 0008-6215 nnns volume:240 year:1993 pages:133-142 http://linkinghub.elsevier.com/retrieve/pii/0008-6215(93)84178-9 GBV_USEFLAG_H ZDB-1-SDJ GBV_NL_ARTICLE AR 240 1993 133-142 |
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(DE-627)NLEJ175503869 (DE-599)GBVNLZ175503869 DE-627 ger DE-627 rakwb eng Bile alcohol glucuronides: regioselective O-glucuronidation of 5β-cholestane-3α,7α,12α,25-tetrol and 24-nor-5β-cholestane-3α,7α,12α,25-tetrol 1993 nicht spezifiziert zzz rdacontent nicht spezifiziert z rdamedia nicht spezifiziert zu rdacarrier A facile and regiocontrolled procedure for the preparation of 5β-cholestane-3α,7α,12α,25-tetrol-3-O-β-d-glucuronide and its corresponding C-26 analogue is described. The method involves direct coupling of bile alcohols, namely, 5β-cholestane-3α,7α,12α-25-tetrol and 24-nor-5β-cholestane-3α,7α,12α,25-tetrol to methyl (tetra-O-acetyl-β-d-glucopyranuronate) in the presence of a Lewis acid, tin(IV) chloride, in dichloromethane. The resulting anomeric pairs of 1,2-trans- and 1,2-cis-glucuronides of tetrols were resolved by analytical and preparative thin-layer chromatography, and their identities were established by high-resolution ^1H NMR spectroscopy and by chemical-ionization and fast-atom-bombardment mass spectrometry. The method described has a practical advantage over the traditional two-step synthesis involving bromides as it is more efficient and uses inexpensive and less toxic materials. It is suggested that these compounds will be useful for studying permeability of the blood-brain barrier in cerebrotendinous xanthomatosis (CTX). Elsevier Journal Backfiles on ScienceDirect 1907 - 2002 Dayal, B. oth Salen, G. oth Padia, J. oth Shefer, S. oth Tint, G.S. oth Sasso, G. oth Williams, T.H. oth in Carbohydrate Research Amsterdam : Elsevier 240(1993), Seite 133-142 (DE-627)NLEJ175413258 (DE-600)1496822-8 0008-6215 nnns volume:240 year:1993 pages:133-142 http://linkinghub.elsevier.com/retrieve/pii/0008-6215(93)84178-9 GBV_USEFLAG_H ZDB-1-SDJ GBV_NL_ARTICLE AR 240 1993 133-142 |
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Bile alcohol glucuronides: regioselective O-glucuronidation of 5β-cholestane-3α,7α,12α,25-tetrol and 24-nor-5β-cholestane-3α,7α,12α,25-tetrol |
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Bile alcohol glucuronides: regioselective O-glucuronidation of 5β-cholestane-3α,7α,12α,25-tetrol and 24-nor-5β-cholestane-3α,7α,12α,25-tetrol |
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Bile alcohol glucuronides: regioselective O-glucuronidation of 5β-cholestane-3α,7α,12α,25-tetrol and 24-nor-5β-cholestane-3α,7α,12α,25-tetrol |
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Bile alcohol glucuronides: regioselective O-glucuronidation of 5β-cholestane-3α,7α,12α,25-tetrol and 24-nor-5β-cholestane-3α,7α,12α,25-tetrol |
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bile alcohol glucuronides: regioselective o-glucuronidation of 5β-cholestane-3α,7α,12α,25-tetrol and 24-nor-5β-cholestane-3α,7α,12α,25-tetrol |
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Bile alcohol glucuronides: regioselective O-glucuronidation of 5β-cholestane-3α,7α,12α,25-tetrol and 24-nor-5β-cholestane-3α,7α,12α,25-tetrol |
| abstract |
A facile and regiocontrolled procedure for the preparation of 5β-cholestane-3α,7α,12α,25-tetrol-3-O-β-d-glucuronide and its corresponding C-26 analogue is described. The method involves direct coupling of bile alcohols, namely, 5β-cholestane-3α,7α,12α-25-tetrol and 24-nor-5β-cholestane-3α,7α,12α,25-tetrol to methyl (tetra-O-acetyl-β-d-glucopyranuronate) in the presence of a Lewis acid, tin(IV) chloride, in dichloromethane. The resulting anomeric pairs of 1,2-trans- and 1,2-cis-glucuronides of tetrols were resolved by analytical and preparative thin-layer chromatography, and their identities were established by high-resolution ^1H NMR spectroscopy and by chemical-ionization and fast-atom-bombardment mass spectrometry. The method described has a practical advantage over the traditional two-step synthesis involving bromides as it is more efficient and uses inexpensive and less toxic materials. It is suggested that these compounds will be useful for studying permeability of the blood-brain barrier in cerebrotendinous xanthomatosis (CTX). |
| abstractGer |
A facile and regiocontrolled procedure for the preparation of 5β-cholestane-3α,7α,12α,25-tetrol-3-O-β-d-glucuronide and its corresponding C-26 analogue is described. The method involves direct coupling of bile alcohols, namely, 5β-cholestane-3α,7α,12α-25-tetrol and 24-nor-5β-cholestane-3α,7α,12α,25-tetrol to methyl (tetra-O-acetyl-β-d-glucopyranuronate) in the presence of a Lewis acid, tin(IV) chloride, in dichloromethane. The resulting anomeric pairs of 1,2-trans- and 1,2-cis-glucuronides of tetrols were resolved by analytical and preparative thin-layer chromatography, and their identities were established by high-resolution ^1H NMR spectroscopy and by chemical-ionization and fast-atom-bombardment mass spectrometry. The method described has a practical advantage over the traditional two-step synthesis involving bromides as it is more efficient and uses inexpensive and less toxic materials. It is suggested that these compounds will be useful for studying permeability of the blood-brain barrier in cerebrotendinous xanthomatosis (CTX). |
| abstract_unstemmed |
A facile and regiocontrolled procedure for the preparation of 5β-cholestane-3α,7α,12α,25-tetrol-3-O-β-d-glucuronide and its corresponding C-26 analogue is described. The method involves direct coupling of bile alcohols, namely, 5β-cholestane-3α,7α,12α-25-tetrol and 24-nor-5β-cholestane-3α,7α,12α,25-tetrol to methyl (tetra-O-acetyl-β-d-glucopyranuronate) in the presence of a Lewis acid, tin(IV) chloride, in dichloromethane. The resulting anomeric pairs of 1,2-trans- and 1,2-cis-glucuronides of tetrols were resolved by analytical and preparative thin-layer chromatography, and their identities were established by high-resolution ^1H NMR spectroscopy and by chemical-ionization and fast-atom-bombardment mass spectrometry. The method described has a practical advantage over the traditional two-step synthesis involving bromides as it is more efficient and uses inexpensive and less toxic materials. It is suggested that these compounds will be useful for studying permeability of the blood-brain barrier in cerebrotendinous xanthomatosis (CTX). |
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Bile alcohol glucuronides: regioselective O-glucuronidation of 5β-cholestane-3α,7α,12α,25-tetrol and 24-nor-5β-cholestane-3α,7α,12α,25-tetrol |
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Dayal, B. Salen, G. Padia, J. Shefer, S. Tint, G.S. Sasso, G. Williams, T.H. |
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Dayal, B. Salen, G. Padia, J. Shefer, S. Tint, G.S. Sasso, G. Williams, T.H. |
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2024-07-06T04:18:46.211Z |
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