The efficient synthesis of a bis-glycosylated steroid drug transport reagent: Methyl 3-β-amino-7α, 12α-di(1' α-glucosyl)-5β-cholate (TC002)

Article abstract of DOI:10.1016/S0960-894X(97)00410-1

The drug transport reagent, methyl 3-β-amino-7α, 12α-di(1'α-glucosyl)-5β-cholate (TC002) 1 was prepared in 15% overall yield from pentaacetyl glucose and methyl cholate. Pentaacetyl glucose was converted to glucosyl sulfoxide 2 in 56% overall yield. Methyl cholate was converted to methyl 3-β-azido cholate 3 in 67% yield. Bis-glycosylation of 3 with 2 followed by a single step reduction provided 1.