Premium
Regioselective α ‐Phosphorylation of Aldoses in Aqueous Solution
Author(s) -
Krishnamurthy Ramanarayanan,
Guntha Sreenivasulu,
Eschenmoser Albert
Publication year - 2000
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/1521-3773(20000703)39:13<2281::aid-anie2281>3.0.co;2-2
Subject(s) - regioselectivity , phosphorylation , chemistry , intramolecular force , reagent , hydrolysis , aqueous solution , phosphate , product (mathematics) , organic chemistry , combinatorial chemistry , stereochemistry , biochemistry , catalysis , geometry , mathematics
Amidotriphosphate and diamidophosphate are reagents for the regioselective α ‐phosphorylation of aldoses. The mechanism involves the carbonyl addition product (see scheme); the hydroxy groups are phosphorylated by an intramolecular phosphate group transfer with formation of a cyclic intermediate, which is then hydrolyzed to the O‐phosphorylated product.