An unexpected rearrangement during Mitsunobu epimerization reaction of sugar derivatives

Rachel Persky, Amnon Albeck

Research output: Contribution to journalArticlepeer-review

21 Scopus citations


Mitsunobu reaction on the glucose derivative (3S,4R,5R,6R)-3,4,5,7- tetrabenzyloxy-6-hydroxy-1-heptene yielded an unexpected rearrangement major product. Its structure was determined as (3R,4R,5R,6S)-4,5,6,7- tetrabenzyloxy-3-hydroxy-1-heptene. The suggested rearrangement mechanism involves an initial intramolecular cyclization, followed by ring opening by the nucleophile p-nitrobenzoate. Product distribution of the Mitsunobu reaction was substrate-dependent, with the corresponding mannose derivative (the 3R epimer) giving less of the initial intramolecular reaction products and the corresponding galactose derivative (the 5S epimer) yielding almost exclusively the expected epimerization product. Varying the Mitsunobu reaction conditions (addition of base and using nonpolar solvent) led to the expected epimerization product of the glucose derivative.

Original languageEnglish
Pages (from-to)3775-3780
Number of pages6
JournalJournal of Organic Chemistry
Issue number12
StatePublished - 16 Jun 2000


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