Sugars chlorodeoxy, synthesis

The potential utility of this method in the synthesis of chlorodeoxy sugars cannot be fully appraised at the present time owing to the lack of sufficient examples. 

An attractive feature in this reaction is the possibility of direct substitution and formation of unblocked sugar derivatives containing one or more chlorodeoxy function in essentially two steps. Another facet is the formation of methyl 4,6-dichloro-4,6-dideoxy-hexosides from certain methyl glycosides in one step. Such compounds could be valuable intermediates in the synthesis of dideoxy and diamino sugars of biological importance. 

Chlorodeoxy sugars by thermal decomposition of O-imino ester chlorides, synthesis of. .. 192 N-( 2-Chloro-l,l,2-trifluoroethyl) -... 

J. K. N. Jones and his colleagues have extensively studied the reaction of sulfuryl chloride with carbohydrates.21-29 This work has elucidated the stereochemical principles involved in the various transformations, and has made available a convenient and effective procedure for the preparation of chlorodeoxy sugars. Several examples of the utility of such derivatives, obtained by way of a reaction with sulfuryl chloride, in the synthesis of other rare sugars are discussed in Section III (see p. 281). In the present Section, the studies on the reaction itself are surveyed. 

A major part of this chapter is concerned with a discussion of a method for the synthesis of chlorodeoxy sugars by direct replacement of hydroxyl groups by chlorim... 

In Section 11.8 a discussion of the reaction of sulfuryl chloride with carbohydrate derivatives is presented, and in Section III are given some experimental procedures representative of this method for the synthesis of chlorodeoxy sugars and procedures of simple processes for the conversion of the chlorodeoxy sugars into other rare sugars. 

S. Hanessian and N. R. Plessas, Reactions of carbohydrates with (halomethylene)dimethyl-iminium halides and related reagents. Synthesis of some chlorodeoxy sugars, J. Org. Chem. 34 2163 (1969). 

Reactions of Sugar Chlorosulfates. Part V. The Synthesis of Chlorodeoxy Sugars, H. 

A Simple Synthesis of Azidodeoxy-sugars via Chlorodeoxy-sugars, B. T. Lawton, W. A. Szarek, and J. K. N. Jones, Chem. Commun., (1969) 787-788. 

Jennings, H J, Jones, J K N, Reactions of sugar chlorosulfates. Part V. The synthesis of chlorodeoxy... 

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