STEREOSELECTIVE SYNTHESIS OF METHYL TETRA-0-METHYL a-AND P-D-GLUCO-AND MANNOPYRANOSIDES

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Abstract:

Methyl tetra - 0-methyl- ?-D- glucopyranoside is stereoselectively prepared from tetramethyl-D- glucopyranose by using (MeI+NaH) in toluene (86%) or cyclohexane (85%), while its ?- isomer is best synthesized in hexamethyl phosphoramide (64%). Similarly, methyl tetra-o-methyl-?- D-mannopyranoside is synthesized in cyclohexane (80%), while its ?- isomer is predominantly prepared by (MeI+n-BuLi) in cyclohexane (98%). The ?-and ?- isomers of these glycosides were identified and quantified by G.C

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volume 3  issue 1

pages  -

publication date 1992-06-01

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