Selective demesylation of 2-O-(methylsulfonyl)-d-mannopyranoside derivatives with sodium amalgam and 2-propanol
✍ Scribed by Kathryn Thresh Webster; Ronald Eby; Conrad Schuerch
- Book ID
- 102640986
- Publisher
- Elsevier Science
- Year
- 1983
- Tongue
- English
- Weight
- 311 KB
- Volume
- 123
- Category
- Article
- ISSN
- 0008-6215
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✦ Synopsis
Note
Selective demesylation of 2-0-(methylsulfonyl)-D-mannopyranoside derivatives with sodium amalgam and 2-propanol
In this laboratory, we have been investigating methods of glycoside and oligosaccharide synthesis that can be conducted in homogeneous solution, with high stereospecificity, at reasonable rates, with near-equivalent amounts of only two reactants. A series of sulfonate leaving-groups of varied reactivity at C-l have been applied to the synthesis of both c&l,2 and trans-1,2 glycosides. If these are used in the D-manno series, a participating substituent on C-2 directs the glycosidation almost exclusively to the 1,2-truns-cu-D-glycoside' ,