Synthesis of deoxy sugars

Despite several attractive features in this method of direct halogen introduction and the obvious applications in the synthesis of deoxy sugars, its uses have not been further exploited by other groups of workers. Some new related methods have become available which reportedly eliminate the difficulties previously encountered such as rearrangement, unreactivity due to steric hindrance, and phosphonate ester formation. The reaction is based on the observation (28) that triethylphosphine reacts with ethanol and carbon tetrachloride to give ethyl chloride, chloroform, and triethylphosphite. In a new adaptation (76, 77) of this... 

Catalytic hydrogenation of benzoylated 3-deoxy-2-enono-1,5-lactones is stereoselective and affords the 3-deoxyaldonolactone derivatives, useful intermediates for the synthesis of deoxy sugars. Thus, 2,4,6-tri-0-benzoyl-3-... 

N. K. Kochetkov and A. I. Usov, The reaction of carbohydrates with triphenyl phosphite methiodide and related compounds. A new synthesis of deoxy sugars, Tetrahedron 79 973... 

A. Kirschning, M. Jesberger, and K. U. Schoning, Concepts for the total synthesis of deoxy sugars, Synthesis (2001) 507-540. 

J. R. Rasmussen, C. J. Slinger, R. J. Kordish, and D. D. Newman-Evans, Synthesis of deoxy sugars. Deoxygenation by treatment with AV -thiocarbonyldiimidazole/tri-n-butylstannane, J. Org. Chem., 46 (1981) 4843-4846. 

E. P. Barrette and L. Goodman, Convenient and stereospecific synthesis of deoxy sugars. Reductive displacement of trifluoromethylsulfonates, J. Org. Chem., 49 (1984) 176-178. 

The reduction of halides or sulfonates is one of the most conventional methods for the synthesis of deoxy sugars. This method is particularly useful for the deoxygenation of primary hydroxyls of carbohydrates. Reduction has been accomplished employing one of the following three methods. 

Cyclization-Mediated Reactions Synthesis of Deoxy Sugars.186... 

Haskell, T H, Woo, P W K, Watson, D R, Synthesis of deoxy sugar. Deoxygenation of an alcohol utilizing a facile nucleophilic displacement step, J. Org. Chem., 42, 1302-1305, 1977. 

Of the halogenated 1,6-anhydrohexopyranoses, the main interest has been directed to the iodo derivatives384,630-632 as intermediates for the synthesis of deoxy sugars, and to the fluoro derivatives (for a review, see Ref. 773), interesting from both the chemical and the biochemical point of view. The chloro and bromo derivatives have been examined only rarely.94,168,319,437... 

Concepts for the total synthesis of deoxy sugars 01S507. 

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