Stereochemical Studies. XXXI. Total Synthesis of Several D-Pentose Derivatives. Stereochemical Courses of the Synthesis of Four Methyl 2, 3-Anhydro-5-O-benzyl-D-pentofuranosides from L-Glutamic Acid and Their Reactions with Nucleophiles

Abstract

Stereoselective synthesis of several D-pentose derivatives from L-glutamic acid without resolution step was performed. Isolation of all possible isomers of methyl 2, 3-anhydro-5-O-benzyl-D-pentofuranosides and their reactions leading to deoxy, amino, and thio derivatives were discussed on the stereochemical ground. Examples in which methoxy group at C₁ exhibits more steric hindrance in the reactions than the benzyloxymethyl group at C₄ are presented.