ChemInform Abstract: A New Oxidative Conversion of Carbohydrate Benzyl Ethers (I) to Benzoyl Esters (II) with RuCl3‐NaIO4.

Abstract

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Nonpyrogenic Molecular Adjuvants Based on norAbu-Muramyldipeptide and norAbu-Glucosaminyl Muramyldipeptide: Synthesis, Molecular Mechanisms of Action, and Biological Activities in Vitro and in Vivo

“…26 Bearing in mind that RuO 4 is very powerful oxidizing agent reaction conditions were carefully adjusted for selective allyl group release in the presence of other protecting groups. 27 Initially, allyl derivative 1 was subject to benzylation to give benzyl 2-acetamido-3-O-allyl-4,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside 2 by treatment with benzyl bromide and sodium hydride in DMF according to published procedure. 18,23,24,28 Glucopyranoside 2 was then treated with NaIO 4 and RuCl 3 in CCl 4 −MeCN−H 2 O at 0 °C (Scheme 1).…”

“…18,23,24,28 Glucopyranoside 2 was then treated with NaIO 4 and RuCl 3 in CCl 4 −MeCN−H 2 O at 0 °C (Scheme 1). 27 In early trial runs In a corresponding manner, amine 9 and its acetyl derivative 10 were prepared as described previously. 21 N-2,2,2-Trichloroethoxycarbonyl (Troc) derivative 11 was prepared by reaction of amine 9 with trichloroethoxycarbonyl chloride in pyridine.…”

“…21 N-2,2,2-Trichloroethoxycarbonyl (Troc) derivative 11 was prepared by reaction of amine 9 with trichloroethoxycarbonyl chloride in pyridine. Thereafter, 10 and 11 were used to prepare intermediate glucosaminyl normuramic acid building blocks 12 and 13 (Scheme 2), 18 then converted to their respective methyl esters 14 27 and 15 by reaction with diazomethane in order to allow complete characterization of these compounds.…”