Syntheses of two kinds of disaccharide subunits of antitumor antibiotic bleomycins. Issue 43 (26th October 2017)

• Record Type: Journal Article
• Authors: Che, Rui; Zhu, Qiwen; Yu, Jie; Li, Jiao; Yu, Jiahui; Lu, Wei
• Is Part Of: Tetrahedron. Volume 73:Issue 43(2017)
• Page Start: 6172
• Page End: 6180
• Publication Date: 2017-10-26
• Subjects: Bleomycins -- Disaccharide -- l-gulose -- 6-Deoxy-l-gulose -- Gram-scale synthesis; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2017.09.009
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: Gram-scale syntheses of two kinds of bleomycin disaccharides are described.l -gulose subunit12 was accomplished with a novel and short route in six steps and 37% overall yield from4, which could be easily prepared from the commercially available inexpensive materiald -sorbitol, while 6-deoxy-l -gulose subunit was synthesized in 11 steps in 8% yield fromd -glucolactone. The disaccharides were then prepared in a previously reported glycosidation coupling of the 3- O -carbamoyl-mannosyl donor with thel -gulopyranoside acceptors. Both disaccharides were finally obtained in gram-scale and the total synthesis of disaccharide2 was achieved the first time. Graphical abstract: