134311-55-0Relevant articles and documents
Synthesis and conformational analysis of substituted 2,6-dioxabicycloheptanes: 1,3-anhydro-2,4-di-O-benzyl-6-deoxy-β-D-glucopyranose by 1H-NMR spectroscopy and molecular mechanics calculation
Wu, Xinfu,Kong, Fanzuo,Lu, Depei,Zhang, Pang
, p. 75 - 88 (2007/10/02)
A highly selective ring opening reduction of methyl 3-O-allyl-2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside provided the 2,4-di-O-benzyl derivative.This was toluenesulfonylated or iodinated and subsequently reduced to give crystalline methyl 3-O-allyl-
Phyllanthoside-Phyllanthostatin Synthetic Studies. 8. Total Synthesis of (+)-Phyllanthoside. Development of the Mitsunobu Glycosyl Ester Protocol
Smith III, Amos B.,Rivero, Ralph A.,Hale, Karl J.,Vaccaro, Henry A.
, p. 2092 - 2112 (2007/10/02)
The first total syntheses of the antineoplastic glycoside (+)-phyllanthoside (1) and the parent disaccharide (-)-phyllanthose (5) have been achieved. Stereoselective Koenigs-Knorr coupling of two 6-deoxyglucose derivatives, bromide 54 and alcohol 55, generated the uncommon 1′ → 2β glycosidic linkage of (-)-phyllanthose. A stereochemically convergent Mitsunobu reaction of protected disaccharide 87 with aglycon carboxylic acid 80, prepared via asymmetric synthesis, then led to 1 of high enantiomeric purity. The Mitsunobu procedure comprises an efficient general method for stereospecific assembly of β-glycosyl esters.