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Paper | Special issue | Vol 95, No. 2, 2017, pp.862-871
Published online, 22nd November, 2016
DOI: 10.3987/COM-16-S(S)54
■ Synthesis of Benzyl Tetra-O-acetyl-α-L-glucopyranoside from Benzyl 2,3-Dideoxy-β-D-erythro-hex-2-enopyranoside

Hayato Okazaki, Yuji Ueda, Kengo Hanaya, Mitsuru Shoji, and Takeshi Sugai*

*Department of Pharmaceutical Science, Keio University, 1-5-30, Shibakoen, Minato-ku, Tokyo 105-8512, Japan

Abstract

Benzyl tetra-O-acetyl-α-L-glucopyranoside was synthesized from benzyl 2,3-dideoxy-β-D-erythro-hex-2-enopyranoside in six steps and 19% overall yield. Epoxidation from the β-side of the double bond between C-2 and C-3 of the starting material along with the subsequent regioselective ring opening by the backside attack of a hydroxide ion at C-3 furnished an intermediate with D-ido-stereochemistry. The inversion at C-5 was performed by an epimerization, by way of an N-cyclohexylenamine, after the chemoselective oxidation at primary hydroxy group of the C-6 to an aldehyde. The present synthesis of L-glucose derivatives implies the sequential stereochemical inversion of C-2 to C-5 of D-glucose. As the present synthesis keeps the whole skeleton and the order of carbon atoms based on the original numbering of D-glucose, it would work well for the synthesis of specifically labeled derivatives, beginning from isotopically labeled D-glucoses.