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Stereoselective synthesis of α- and β-C-glucosides via radical cyclization with an allylsilyl tether. Control of the stereoselectivity by changing the conformation of the pyranose ring

✍ Scribed by Satoshi Shuto; Masaru Terauchi; Yumi Yahiro; Hiroshi Abe; Satoshi Ichikawa; Akira Matsuda

Book ID: 104210323
Publisher: Elsevier Science
Year: 2000
Tongue: French
Weight: 164 KB
Volume: 41
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)00556-6

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✦ Synopsis

An efficient method for preparing both 1α-and 1β-C-glucosides having a 3-hydroxypropyl group at the anomeric position via a radical cyclization reaction with an allylsilyl tether was developed. The stereoselectivity of the radical cyclization can be controlled by the conformation of the pyranose ring, which is effectively manipulated by the hyroxyl protecting groups.

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