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

Research output: Contribution to journalArticle

1 Citation (Scopus)

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.

Original languageEnglish
Pages (from-to)862-871
Number of pages10
JournalHeterocycles
Volume95
Issue number2
DOIs
Publication statusPublished - 2017

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Glucose
Derivatives
Stereochemistry
Epoxidation
Skeleton
Aldehydes
Carbon
Atoms
Oxidation
benzyl glucopyranoside
hydroxide ion

ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

Cite this

Synthesis of benzyl tetra-O-acetyl-α-L-glucopyranoside from benzyl 2,3-dideoxy-β-D-Erythro-hex-2-enopyranoside. / Okazaki, Hayato; Ueda, Yuji; Hanaya, Kengo; Shoji, Mitsuru; Sugai, Takeshi.

In: Heterocycles, Vol. 95, No. 2, 2017, p. 862-871.

Research output: Contribution to journalArticle

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AB - 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.

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