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Radical Rearrangements of 2‐ O ‐(Diphenoxyphosphoryl)glycosyl Bromides
Author(s) -
Koch Andreass,
Giese Bernd
Publication year - 1993
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19930760426
Subject(s) - chemistry , glycosyl , nuclear magnetic resonance spectroscopy , radical , stereochemistry , medicinal chemistry , organic chemistry
A variety of 2‐deoxy‐1‐ O ‐diphenoxylphosphoryl‐hexopyranoses were generated in situ by a radical 2→1 migration of the phosphate group. The structures of the reactive rearrangement products were fully elucidated by NMR spectroscopy. Rate constants for this new rearrangement were determined fro a variety of substrates.