title: 2,3-Unsaturated allyl glycosides as glycosyl donors for selective α-glycosylation.
abstract: In the presence of NBS and a catalytic amount of a Lewis acid, 2,3-unsaturated allyl glycosides [6-(allyloxy)-3,6-dihydro-2-(hydroxymethyl)-2H-pyran-3-ol] have been successfully used as versatile glycosyl donors for the stereoselective α-glycosylation of a variety of alcohols comprising sensitive functions such as acetonide, keto, nitro, and ester in 50-90% yields. The methodology offers an equally facile alternative to 4-pentenyl replacement in unsaturated sugars.
authors: Bio-organic Chemistry Division, Indian Institute of Integrative Medicine (CSIR), Canal Road, Jammu, India-180001.
authors: Brijesh
authors: B
authors: Kumar
authors: Mushtaq A
authors: MA
authors: Aga
authors: Abdul
authors: A
authors: Rouf
authors: Bhahwal A
authors: BA
authors: Shah
authors: Subhash C
authors: SC
authors: Taneja
mesh_terms: D000438:Alcohols / Q000737:chemistry; D006027:Glycosides / Q000737:chemistry*; D006031:Glycosylation; D011714:Pyrans / Q000737:chemistry; D013379:Substrate Specificity; D013438:Sulfhydryl Compounds / Q000737:chemistry
chemical_list: D000438:Alcohols; D006027:Glycosides; D011714:Pyrans; D013438:Sulfhydryl Compounds