
TY  - JOUR
A1  - Guthrie, RD 
A1  - Jenkins, ID 
T1  - Epoxidation with triphenylphosphine and diethyl azodicarboxylate. II. Methyl 4,6-O-benzylidene-D-aldohexopyranosides
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1981
VL  - 34
IS  - 9
SP  - 1997
EP  - 2000
KW  - 
UR  - https://doi.org/10.1071/CH9811997 
N2  - Epoxidation of the conformationally rigid diaxial diol methyl 4,6-O-benzylidene-&#945;-D-altropyranoside with triphenylphosphine and diethyl azodicarboxylate proceeds in high yield under very mild conditions to give the corresponding 2,3-anhydro-D-mannoside. By contrast, the corresponding diequatorial diol, methyl 4,6-0-benzylidene-&#945;-D-glucopyranoside, undergoes epoxidation only under forcing conditions and gives the D-allo isomer. Evidence is presented for the formation of a cyclic phosphorane intermediate in the latter case. 
ER  -

