Synthesis of “dihydroacarbose”, an α-d-glucosidase inhibitor having a pseudo-tetrasaccharide structure (original) (raw)

1989, Carbohydrate Research

"Dihydroacarbose" (2)) an aD -glucosidase inhibitor having a pseudo-tetrasaccharide structure, was synthesized by reductive coupling of 43-amine-11,61anhydro-21,31,22,32,62,23,33-hepta-0-benzyl-43,63-dideoxy-P-maltotriose and 2~-(2,4/3,5)-2,3,Ctris(benzyloxy)-S-(trityloxymethyl)cyclohexanone with sodiumcyanoborohydride. The former intermediate was prepared from a partially benzylated 11,61-anhydro-/3-maltotriose, and the latter was prepared from a chiral, pentasubstituted cyclohexene derived from D-glucose. The synthetic 2 was found to be a strong, non-competitive inhibitor (Ki = 1.13 X 10-6~) against small-intestinal sucrase of rat.