2-C-branched glycosides from 2'-carbonylalkyl 2-O-Ms(Ts)-C-glycosides. A tandem SN2-SN2 reaction via 1,2-cyclopropanated sugars
| Autor: | Sanchai Ekthawatchai, Shih-Hsiung Wu, Wei Zou, Huawu Shao |
|---|---|
| Rok vydání: | 2004 |
| Předmět: |
chemistry.chemical_classification
Anomer Molecular Structure Organic Chemistry Glycoside Stereoisomerism Biochemistry Catalysis chemistry.chemical_compound chemistry Nucleophile Intramolecular force SN2 reaction Organic chemistry Indicators and Reagents Azide Glycosides Sulfhydryl Compounds Physical and Theoretical Chemistry |
| Zdroj: | Organic letters. 6(20) |
| ISSN: | 1523-7060 |
| Popis: | [reaction: see text] Under basic conditions, 2'-aldehydo (acetonyl) 2-O-Ms(Ts)-alpha-C-glycosides undergo an intramolecular S(N)2 reaction to form 1,2-cyclopropanated sugars, which react with nucleophiles (alcohols, thiols, and azide) at the anomeric carbon to give 2-C-branched glycosides. By way of contrast, the 1,2-cyclopropanes derived from 2'-ketones only react with thiols to give 2-C-branched thioglycosides. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|