3,3-Diphenyl-2-Morpholinone Derivatives Of 2-Amino-2-Deoxy-D-Allose.

Author

Ram Babu, University of the Pacific

Date of Award

1975

Document Type

Dissertation

Degree Name

Doctor of Philosophy (Ph.D.)

Department

Chemistry

First Advisor

Paul H. Gross

First Committee Member

Donald K. Wedegaertner

Second Committee Member

Richard P. Dodge

Third Committee Member

Charles A. Matuszak

Fourth Committee Member

Fuad M. Nahhas

Abstract

A new cyclic protective group has been fused to the cis amino alcohol group of benzyl 2-amino-3,5-o-benzylidene-2-deoxyβ-D-Allopyranoside, by way of a unique rearrangements mechanism. To establish the 2-morpholinone structure, chemical studies, such as reduction and acetylation were conducted.

Comparative spectroscopic studies using ir, pmr, and C-13 nmr confirmed the assigned structures.

The 2-morpholinone ring was cleaved by mild alkaline hydrolysis and could be closed again with acetic anhydride in pyridine. An oxazolidinone derivation of benzyl 2-amino-4,6-o-benzylidene-2-deoxyβ-D-allopyranoside was prepared in a quantitative yield by a modification of a known method.

Protective group properties of the oxazolidinone were studied prior to the examination of the 2-morpholinone cyclic protective group. The selective removal of the benzyl aqlycon was achieved in excellent yield by catalytic hydrogenation, for both morpholinone and oxazolidinone protected benzyl-β-D-Allopyranoside. The selective removal of the 4,6-o-benzylidone group in presence of a 2-morpholinone ring was possible in high yield. The cleavage of the 2-morpholinone protective group was accomplished in two steps. Mild alkaline hydrolysis cleaved the ester function of the ring and mild acidic hydrolysis cleaved its amino function.

Pages

88

Recommended Citation

Babu, Ram. (1975). 3,3-Diphenyl-2-Morpholinone Derivatives Of 2-Amino-2-Deoxy-D-Allose.. University of the Pacific, Dissertation. https://scholarlycommons.pacific.edu/uop_etds/3204