A new route to the disaccharide moiety (2-O-(3-O-carbamoyl-a-D-mannopyranosyl)-L-gulopyranose) of the antitumor agent bleomycin was develolfed. Both the L-gulose synthon 21 and the 3-O-carbamoyl-D-mannose segment 30 were prepared from D-mannose in a regioselective manner by applying stannylene aceta
Total synthesis of the disaccharide of bleomycin, 2-0-(α-D-mannopyranosyl)-L-gulopyranose
✍ Scribed by Tsutomu Tsuchiya; Toshiaki Miyake; Shunji Kageyama; Sumio Umezawa; Hamao Umezawa; Tomohisa Takita
- Publisher
- Elsevier Science
- Year
- 1981
- Tongue
- French
- Weight
- 227 KB
- Volume
- 22
- Category
- Article
- ISSN
- 0040-4039
No coin nor oath required. For personal study only.
📜 SIMILAR VOLUMES
Partial oxyamination of 4,6-di-0-acetyl-2,3-dideoxy-cu-D-erythro-hex-2enopyranosyl 4,6-di-O-acetyl-2,3-dideoxy-a-D-erythro-hex-Zenopyranoside with chloramine-T and osmium tetraoxide gave 4,6-di-0-acetyl-2-deoxy-2-(p-toluenesulfonamide)-a-D-mannopyranosyl 4,6-di-0-acetyl-2,3-dideoxy-ry-D-erythro-hex-
The trisaccharide a-D-Manp-( l-+2)-a-D-Manp-(l-+2)-D-Man was synthesised by using a stepwise method. A key reaction in the preparation of the intermediates was the selective hydrogenolysis of mannopyranoside derivatives having both dioxane-and dioxolane-type benzylidene acetals, resulting in the exc
Treatment of methyl 3-O-benzyl-2-O-(2,3,4,6-tetra-O-acetyl-alpha-D-mannopyranosyl)-alpha-D- mannopyranoside (1) with tert-butyldiphenylsilyl chloride in N,N-dimethylformamide afforded methyl 3-O-benzyl-6-O-tert-butyldiphenylsilyl-2-O-(2,3,4,6-tetra-O-acetyl -alpha-D- mannopyranosyl)-alpha-D-mannopyr