82598-89-8Relevant academic research and scientific papers
Stereoselective synthesis of (E)-mannosylidene derivatives using the Wittig reaction
Coumbarides, Gregory S.,Motevalli, Majid,Muse, Warda A.,Wyatt, Peter B.
, p. 7888 - 7891 (2007/10/03)
(Chemical Equation Presented) Stabilized ylides Bu3P=CH(EWG), where EWG is an ester or nitrile group, react with 2,3,4,6-tetra-O- benzylmannono-1,5-lactone giving high yields of mannosylidene derivatives; in contrast to the glucose and galactos
Stereochemistry in the synthesis and reaction of exo-glycals.
Yang, Wen-Bin,Yang, Yu-Ying,Gu, Yu-Feng,Wang, Shwu-Huey,Chang, Che-Chien,Lin, Chun-Hung
, p. 3773 - 3782 (2007/10/03)
Two general methods are explored for the stereoselective synthesis of exo-glycals. One method utilizes a nucleophilic addition of fully protected sugar lactones of gluco-, galacto-, and manno-types, followed by the subsequent dehydration, to give the desired exo-glycals with (Z)-configuration. The other method proceeds with selenylation of C-glycosides in a stereoselective manner. The subsequent selenoxide elimination also provides (Z)-exo-glycals. The prepared exo-glycal conjugated esters of either gluco- or manno-type react with allyl alcohol to give exclusively alpha-anomers.
The Wittig-Horner Reaction on 2,3,4,6-Tetra-O-benzyl-D-mannopyranose and 2,3,4,6-Tetra-O-benzyl-D-glucopyranose
Allevi, Pietro,Ciuffreda, Pierangela,Colombo, Diego,Monti, Diego,Speranza, Giovanna,Manitto, Paolo
, p. 1281 - 1283 (2007/10/02)
The synthetic utility of the Wittig-Horner reaction in the synthesis of C-glycosides is illustrated by the preparation of the α- and β-glycosyl acetates of the 2,3,4,6-tetra-O-benzyl-D-mannopyranose and of the 2,3,4,6-tetra-O-benzylglucopyranose.A partial epimerization of the C-2 carbon of the starting protected carbohydrate is observed.
