
TY  - JOUR
A1  - McAuliffe, Joseph C. 
A1  - Skelton, Brian W. 
A1  - Stick, Robert V. 
A1  - White, Allan H. 
T1  - &#946;-Acarbose. IV. Model Studies on the Alkylation of Cyclohexylamine with a Carbohydrate Epoxide
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1997
VL  - 50
IS  - 3
SP  - 209
EP  - 218
KW  - 
UR  - https://doi.org/10.1071/C96154 
N2  - 1,6:3,4-Dianhydro-2-O-benzyl-&#946;-D-galactose has been treated with cyclohexylamine to give an amino alcohol, convertible into 2,3-di-O-acetyl-1,6-anhydro-4-cyclohexylamino-4-deoxy-&#946;-D-glucose by reduction and acetylation. The anhydro bridge of this diacetate has been successfully opened under acetolysis conditions. The original amino alcohol has also been converted into a cyclic carbamate, a carbamate and an aziridine, by utilizing a variety of reagents and conditions. The 1,6-anhydro bridge of the cyclic carbamate, also containing a 2-O-benzyl ether, could be opened under acetolysis conditions but a comparable reaction was best done on the derived 2-O-acetyl compound. The resulting mixture of D-glucosyl acetates, still containing a cyclic carbamate, was convered into a methyl &#946;-D-glucoside. The cyclic carbamate could be removed by hydrolysis with aqueous base to give a model glycoside for a synthesis of &#946;-acarbose. Single-crystal X-ray structure determinations are reported for 2,3-di-O-acetyl-4-&#91;acetyl(cyclohexyl)amino&#93;-1,6-anhydro-4-deoxy-&#946;-D-glucose, 1,6-anhydro-2-O-benzyl-3,4-&#91;N-(cyclohexyl)epimino&#93;-3,4-dideoxy-&#946;-D-allose and methyl 2,6-di-O-acetyl-3,4-O,N-carbonyl-4-cyclohexylamino-4-deoxy-&#946;-D-glucoside. 
ER  -

