Stereoselective synthesis of 2-S-ethyl(phenyl)-2-thio-beta-glucopyranosides via 1,2-migration and concurrent glycosidation of ethyl(phenyl) 2,3-orthoester-1-thio-alpha-mannopyranosides.
1,2-Migration and concurrent glycosidation of ethyl(phenyl) 2,3-orthoester-1-thio-alpha-D- and L-mannopyranosides under the action of TMSOTf readily afforded the corresponding 2-S-ethyl(phenyl)-2-thio-beta-glucopyranosides, ready precursors to 2-deoxy-arabino-hexopyranosides (2-deoxy-beta-glucopyranosides).
Yang
Z
Z
State Key Laboratory of Bio-organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, People's Republic of China.
Yu
B
B
D002236:Carbohydrate Conformation; D005960:Glucosides / Q000138:chemical synthesis*; D006027:Glycosides / Q000737:chemistry; D006031:Glycosylation; D008358:Mannose / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D005960:Glucosides; D006027:Glycosides; D008358:Mannose