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, Takeshi Sugai

研究成果: Article査読

1 被引用数 (Scopus)

抄録

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.

本文言語English
ページ(範囲)862-871
ページ数10
ジャーナルHeterocycles
95
2
DOI
出版ステータスPublished - 2017

ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

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