192506-73-3Relevant academic research and scientific papers
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.
