| Efficient synthesis of omega-mercaptoalkyl 1,2-trans-glycosides from sugar peracetates. | |
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MedLine Citation:
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PMID: 17362892 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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Lewis acid-promoted reactions of peracetylated sugars (glucose, galactose, maltose, lactose) with omega-bromo-1-alkanols (C(8), C(12)) were investigated. ZnCl(2) was found to promote the 1,2-trans-glycosylation of the alcohols in toluene at about 60 degrees C in a stereocontrolled manner with better yields than commonly employed promoters such as SnCl(4). The omega-bromoalkyl acetylated glycosides were readily converted to omega-mercaptoalkyl glycosides, which are useful for the preparation of glycoclusters. |
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Authors:
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Teiichi Murakami; Reiko Hirono; Yukari Sato; Kiyotaka Furusawa |
Publication Detail:
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Type: Journal Article Date: 2007-02-25 |
Journal Detail:
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Title: Carbohydrate research Volume: 342 ISSN: 0008-6215 ISO Abbreviation: Carbohydr. Res. Publication Date: 2007 Jun |
Date Detail:
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Created Date: 2007-04-16 Completed Date: 2007-08-01 Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 0043535 Medline TA: Carbohydr Res Country: Netherlands |
Other Details:
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Languages: eng Pagination: 1009-20 Citation Subset: IM |
Affiliation:
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Institute for Biological Resources and Functions, National Institute of Advanced Industrial Science and Technology (AIST), Tsukuba Central 5, Tsukuba, Ibaraki 305-8565, Japan. t-murakami@aist.go.jp |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Acetates* Acetylation Alcohols / metabolism Carbohydrate Conformation Carbohydrates / chemistry Disaccharides / chemical synthesis, chemistry Glucose / chemistry Glycosides / chemical synthesis* Glycosylation Hexoses / metabolism* Models, Molecular Oligosaccharides / chemical synthesis Proteins / chemistry |
| Chemical | |
Reg. No./Substance:
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0/Acetates; 0/Alcohols; 0/Carbohydrates; 0/Disaccharides; 0/Glycosides; 0/Hexoses; 0/Oligosaccharides; 0/Proteins; 50-99-7/Glucose |
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