One-Pot Synthesis of Tri-Acetalated Aldohexoses with 1,1-Dialkoxycyclohexane-p-Toluenesulfonic Acid
Title:
One-Pot Synthesis of Tri-Acetalated Aldohexoses with 1,1-Dialkoxycyclohexane-p-Toluenesulfonic Acid
Author:
Kiso, Makoto Yasui, Akiyo Hasegawa, Akira
Appeared in:
Journal of carbohydrate chemistry
Paging:
Volume 2 (1983) nr. 4 pages 449-456
Year:
1983
Contents:
2-Deoxy-d-arabino-hexose (1), 2-acetamido-2-deoxy-d-glucose (2), and 2-deoxy-2-trifluoroacetamido-d-glucose (3) were each treated with 1,1-dimethoxycyclohexane or 1,1-dibenzyloxycyclohexane in 1,4-dioxane in the presence of p-toluenesulfonic acid. The major products were the 1,1-dimethyl or 1,1-dibenzyl acetals (4-9) of 3,4:5,6-di-O-cyclohexylidene-2-deoxy-aldehydo-d-arabino-hexose, and of 2- (acylamino)-3,4:5,6-di-O-cyclohexylidene-2-deoxy-aldehydo-D-glucose. The dibenzyl acetal derivatives were converted, by hydro-genolysis, into the corresponding, acyclic aldehydes (10-12) in good yields.