Eine neue, einfache Synthese des. 1‐O‐Acetyl‐2,3,5‐Tri‐O‐benzoyl‐β‐D‐Ribofuranosides

Abstract

A new simple 3‐step synthesis of 1‐O‐acetyl‐2,3,5‐tri‐O‐benzoyl‐β‐Dribofuranoside is described. D‐Ribose is methylated to 1‐O‐methylribofuranoside and the latter benzoylated to 1‐O‐methyl‐2,3,5‐tri‐O‐benzoyl‐D‐ribofuranoside. Acetolysis with a mixture of acetic acid, acetic anhydride and sulfuric acid furnishes directly and in good yield pure 1‐O‐acetyl‐2,3,5‐tri‐O‐benzoyl‐β‐D‐ribofuranoside.

2′-C-Methyl Branched Pyrimidine Ribonucleoside Analogues: Potent Inhibitors of RNA Virus Replication

“…In this case, the corresponding precursor 8 (Du et al, 1999) was not as readily available and needed to be synthesized. Starting from L-ribose, compound 6 was obtained following the three-step sequence developed for the corresponding D-enantiomer (Recondo & Rinderknet 1959), and isolated as its β-anomer by crystallization from ethanol with a 39% overall yield. Hydrogen bromide treatment of 6 followed by water addition led to the bicyclic derivative 7.…”

Progress in 7-Deazapurine - Pyrrolo[2,3-d]pyrimidine - Ribonucleoside Synthesis

“…formed with HMDS in the presence of chlorotrimethylsilane (10 h), was glycosylated with the peracylated sugar 33 [64] in dichloroethane in the presence of TMSOTf for 21 hours (Scheme 13). According to neighbour group participation the acyloxonium ion 51 is formed as the intermediate which is attacked by the nucleophile (7-deazapurine 15a) from the ßface (Baker's trans rule).…”

Spiegelmers for Therapeutic Applications – Use of Chiral Principles in Evolutionary Selection Techniques

“…Starting from l-ribose the intermediate 1-O-acetyl-2,3,5-tri-O-benzoyl-l-ribose (l-ATBR) is obtained in three steps (Fig. 18.7A) (Recondo and Rinderknecht, 1959). l-ATBR is the common starting material for all four l-nucleosides.…”