Full acetals of β-d-glycopyranosylnitromethanes and a 1, 2-dideoxy-1-nitroalk-1-enitol derived from common hexoses

DP Pham-Huu, M Petrušová, JN BeMiller, P Köll…

Index: Pham-Huu, Duy-Phong; Petrusova, Maria; BeMiller, James N.; Petrus, Ladislav Journal of Carbohydrate Chemistry, 2000 , vol. 19, # 1 p. 93 - 110

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Citation Number: 11

Abstract

Kinetically controlled O-isopropylidenation of common 2, 6-anhydro-1-deoxy-1-nitroalditols (β-d-glycopyranosylnitromethanes) derived from d-glucose, d-galactose, and d-mannose with 2-methoxypropene in 1, 2-dimethoxyethane catalyzed with 4-toluenesulfonic acid afforded high yields of 2, 3; 4, 6-di-O-isopropylidene acetals. With d-mannose, the bisacetal was also obtained in quantitative yield by reaction with 2, 2-dimethoxypropane. Mono-O- ...