G. Kovacs, K. Tóth, Z. Dinya,
Apr 16, 1999
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0
Influential Citations
16
Citations
Journal
Tetrahedron
Abstract
Abstract Reactions of 2,3,4,6- tetra -O- acetyl -α- d -glucopyranosyl bromide (3) with chromium(II)L complexes (L = EDTA, NTA, IDA, GLY, MAL) in neutral (5 3,4,6- tri -O- acetyl-1,5-anhydro-2-deoxy- d -arabino- hex-1-enitol (13) in 70–90% yields and >95% purity. Complexes of Cr(II) with L = EDTA, NTA were similarly efficient with 2,3,4,6- tetra -O- acetyl -α- d -glucopyranosyl chloride (2) in furnishing glucal 13, while with L = IDA, GLY, MAL hydrolysis of 2 could not be suppressed. Under the same conditions [CrII(EDTA)]2− also efficiently gave the corresponding glycals 14–19 from 2,3,4,6- tetra -O- benzoyl - ( 4 ) and 2,3,4,6- tetra -O- pivaloyl -α- d -glucopyranosyl bromide (5), per-O-acetylated α- d -galactopyranosyl chloride (6) and bromide (7), α- d -mannopyranosyl chloride (8), α- d -xylopyranosyl chloride (9), and bromide (10), β- d -arabinopyranosyl bromide (11), and α- l -rhamnopyranosyl chloride (12).