Thiosugars. VII. Synthesis of 1-Thio-2-deoxy-β-D-glucose Derivatives

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概要

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• 1-Thio-2-deoxy-β-D-glucose sodium salt dihydrate (X), m.p. 114〜115°, [α]^<15>_D+22°was prepared starting from 3,4,6-tri-O-acetyl-D-glucal (I) via 2-deoxy-3,4,6-tri-O-acetyl-D-glucopyranosyl bromide (VII) and 2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranosyl ethylxanthate (VIII). The product afforded 2-deoxy-D-glucose anilide, benzyl 1-thio-2-deoxy-β-D-glucoside, m.p. 96〜97°, [α]^<21>_D-242°, and benzyl 1-thio-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucoside, m.p. 60〜61°, [α]^<16>_D-192°. The optical rotatory dispersion of VIII reveals the similarity with that of 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl ethylxanthate, which supports the β-configuration of VIII, together with that of the compounds derived from VIII. Heating of I with thioacetic acid for 5.5 hours in the presence of a small amount of sulfuric acid, afforded crystals, m.p. 104〜105°, [α]^<22>_D+164°, in 60% yield. The structure was assigned to be 1-S-acetyl-1-thio-2,3-didehydro-2,3-dideoxy-4,6-di-O-acetyl-α-D-eryhtro-hexose (II).

• 公益社団法人日本薬学会の論文
• 1965-07-25

著者

• 赤木 満洲雄

  Faculty of Pharmaceutical Sciences, School of Medicine, Hokkaido University

• 手島 節三

  Faculty of Pharmaceutical Sciences, Nagoya City University

• 手島 節三

  Faculty Of Pharmaceutical Sciences Nagoya City University

• 中村 博

  Faculty Of Pharmaceutical Sciences Hokkaido University

• 赤木 満洲雄

  Faculty Of Pharmaceutical Sciences Hokkaido University

• 槙 孝雄

  Faculty Of Pharmaceutical Sciences School Of Medicine Hokkaido University

関連論文

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