Bioorganic and Medicinal Chemistry Letters p. 2251 - 2254 (1997)
Update date:2022-08-03
Topics: Characterization Deprotection Isolation and Purification Starting Material Protection of Hydroxyl Groups Protection of the Amino Group
Sofia, Michael J.
Kakarla, Ramesh
Kogan, Natan
Dulina, Richard
Hui
Hatzenbuhler, Nicole T.
Liu, Dashan
Chen, Anna
Wagler, Thomas
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.
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