Process for the preparation of chlorosulfate and sulfamate derivatives of 2,3:4,5-bis-O-(1-methylethylidene)-.beta.-D-fructopyranose and (1-methylcyclohexyl)methanol

A two step process for synthesizing sulfamates of the formula I:

• ##STR22## wherein X is CH.sub.2 or oxygen;
• R.sub.1 is hydrogen or C.sub.1 -C.sub.4 alkyl;
• and
• R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are independently hydrogen or alkyl, and, when X is oxygen, any of R.sub.2 and R.sub.3, or R.sub.4 and R.sub.5, together, may be a methylenedioxy group of the formula (IV):
• ##STR23## wherein R.sub.6 and R.sub.7 are the same or different and are hydrogen, alkyl or are alkyl joined together to form a cyclopentyl or cyclohexyl ring, with the proviso that R.sub.6 and R.sub.7 may not both be H at the same time;
• the process comprising in a first step, reacting an alcohol of the formula RCH.sub.2 OH, wherein R is a moiety of the formula II:
• ##STR24## with sulfuryl chloride in the presence of a base selected from the consisting of pyridine, pyridine derivatives and triethylamine in a solvent of toluene to form a chlorosulfate compound of the formula III:
• RCH.sub.2 OSO.sub.2 Cl;
• and in a second step reacting the chlorosulfate compound of formula III with an amine of the formula R.sub.1 NH.sub.2 in a solvent of tetrahydrofuran to produce the sulfamate of formula I.