Nucleosides, Nucleotides and Nucleic Acids

D-Arbinose-Based Synthesis of homo-C-d4T and homo-C-thymidine

B Doboszewski

Index: Doboszewski, Bogdan Nucleosides, Nucleotides and Nucleic Acids, 2009 , vol. 28, # 10 p. 875 - 901

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Citation Number: 7

Abstract

2, 3, 5-Tri-O-benzyl-D-arabinofuranosyl halides (chloride, bromide) were reacted with AllMgBr, MeMgBr, and VinMgBr to furnish anomeric mixtures of the C-glycosyl products. The factors that influenced the β/α ratio are discussed. The α, β-C-vinyl derivative was transformed into 1-deoxy-1-C-hydroxymethyl-β-and-α-D-arabinofuranoses (2, 5-anhydro-D- glucitol and-mannitol, respectively), separable after isopropylidenation step. 2, 5-Anhydro- ...