Volume 22, Issue 39
Natural Products
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ChemInform Abstract: Structural Elucidation of the Cyclic Products Formed by the Reaction of 2,3-O-Isopropylidene Derivatives of aldehydo-Aldose with Allylsilanes, Vinyl Ethers, or Vinyl Sulfides in the Presence of Boron Trifluoride Etherate.

H. SUGIMURA

H. SUGIMURA

Noguchi Inst., Itabashi-ku, Tokyo 173, Japan

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First published: October 1, 1991

Abstract

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ChemInform Abstract

The aldehyde (I) mentioned in the title reacts with the vinyl sulfide ( II) in the presence of boron trifluoride etherate to form the hemicyclic O,S-acetal (III) which is converted to the thioglycoside (V) or the heptitol derivative (VI). (I) and the cinnamylsilane (VII) produce the tetrahydrofuran (VIII) which is transformed into (IX). (I) and the styryl ether (X) give the acetal (XI).

chemical structure image

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