Thiosugars Iii. Stereoselective Approach to β-(1→2)-2,3-Dideoxy-2-<i>C</i>-Acetamidomethyl-2-<i>S</i>-Thiodisaccharides From Levoglucosenone

Abstract

ABSTRACT β-(1→2)-2,3-Dideoxy-2-C-acetamidomethyl-2-S-thiodisaccharides were synthesized in four steps by a stereoselective base catalyzed Michael addition reaction of 1-thiosugars to α-nitroalkene 4a, a new chiral synthon from levoglucosenone. It was followed by the reduction of the nitro group with a sodium borohydride/cobalt chloride complex and the hydrolytic opening of the 1,6-anhydro ring.