D-erythro-Pentofuranoside, ethyl 2-deoxy- synthesis

Yield:91784-10-0 68%

Reaction Conditions:

with sodium tetrahydroborate;ethanol

Steps:

8

A furanolactone, a commercially available, non-carbohydrate and achiral, is used as starting material to obtain a chlorosugar. The key step in this approach is the asymmetric dihydroxylation of the 2Z-pentenoate ester 2 to form the 2(R),3(R)-pentanoate derivative 3. Intermediate 3 is subjected to stereoselective cyclization to give the 2-deoxy L-sugar 4. Compound 4 is converted to the desired protected chlorosugar in three straightforward synthetic transformations. See D.C. Liotta, and M. W. Hager, U.S. Pat. No. 5,414,078, May 9, 1995.

References:

US2005/59632,2005,A1 Location in patent:Page/Page column 25