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Regio and stereoselective conversion of Δ4-uronic acids to l-Ido- and d-glucopyranosiduronic acids

✍ Scribed by Hélène G Bazin; Robert.J Kerns; Robert J Linhardt

Book ID: 104256259
Publisher: Elsevier Science
Year: 1997
Tongue: French
Weight: 254 KB
Volume: 38
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(96)02514-2

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✦ Synopsis

Synthesis of L-ido-and D-glucopyranosiduronic acids was performed starting from protected A4-uronic acids 3a-f, Bromination of the C-4,5 double bond provided the trans-diaxial bromohydrin derivatives 6a-d, which were converted to the corresponding epoxides 7a-d in high yields. Direct reduction of these epoxides using borane-tetrahydrofuran complex afforded the D-glucopyranosiduronic acids 9b-d, while Lewis acid reatrangment through the C-4 keto intermediate 10b-d afforded the Lidopyranosiduronic acids llb-d.

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