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Diastereoselective free-radical synthesis of α-substituted C-glycosyl phosphonates, and their use as building blocks in the HWE-reaction

✍ Scribed by Hans-Dieter Junker; Nga Phung; Wolf-Dieter Fessner

Publisher: Elsevier Science
Year: 1999
Tongue: French
Weight: 266 KB
Volume: 40
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(99)01459-8

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✦ Synopsis

C-Glycosidic phosphonates were synthesized by the addition of pyranosidic and furanosidic glycosyl radicals to ot-phosphonoacrylates which occurred with high diastereoselectivity towards the formation of n-C-glycosidic phosphonates. The products are useful substrates for the synthesis of complex higher-carbon sugars related to tunicamycin by Horner-Wadsworth-Emmons reactions.