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A Simple Procedure for the Synthesis of Carbohydrate Ortholactones

✍ Scribed by Žagar, Cyrill ;Scharf, Hans-Dieter

Publisher
John Wiley and Sons
Year
1993
Tongue
English
Weight
354 KB
Volume
1993
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

3,4‐Di‐O‐benzyl‐2,6‐dideoxy‐L‐arabino‐hexono‐1,5‐lactone (1b) was synthesized in three steps by starting from di‐O‐acetyl‐L‐rhamnal (6). Sequential treatment of 1b or 3,4,6‐tri‐O‐benzyl‐2‐deoxy‐D‐arabino‐hexono‐1,5‐lactone (1a) with triethyloxonium tetrafluoroborate and sodium ethanolate produced the diethyl ortholactones 2a and b. Acid‐catalyzed reaction of 2a or b with 1,2‐ethanediol (5a) or (1__S__,2__S__)‐1,2‐cyclohexanediol (5b) gave the spiro ortholactones 3a, b, and 4a, b.

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