Tetrahedron
Tetrahedron
5 years ago

Syntheses of two kinds of disaccharide subunits of antitumor antibiotic bleomycins

Syntheses of two kinds of disaccharide subunits of antitumor antibiotic bleomycins
Gram-scale syntheses of two kinds of bleomycin disaccharides are described. l-gulose subunit 12 was accomplished with a novel and short route in six steps and 37% overall yield from 4, which could be easily prepared from the commercially available inexpensive material d-sorbitol, while 6-deoxy-l-gulose subunit was synthesized in 11 steps in 8% yield from d-glucolactone. The disaccharides were then prepared in a previously reported glycosidation coupling of the 3-O-carbamoyl-mannosyl donor with the l-gulopyranoside acceptors. Both disaccharides were finally obtained in gram-scale and the total synthesis of disaccharide 2 was achieved the first time.

Publisher URL: www.sciencedirect.com/science

DOI: S0040402017309316

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