Synthesis of Methyl 2,6-Dideoxy-3-C-Methyl-α-D-ribo- hexopyranoside (Methyl α-D-Mycaroside), a Component of the Antitomor Agent Mithramycin
- 1 June 1985
- journal article
- research article
- Published by Taylor & Francis in Journal of Carbohydrate Chemistry
- Vol. 4 (2) , 227-242
- https://doi.org/10.1080/07328308508058834
Abstract
Methyl α-D-mannopyranoside (4) was converted into methyl 2,6-dideoxy-3-C-methyl-ct-D-ribo-hexopyranoside (20) (methyl α-D-mycaroside) by an efficient sequence of reactions (Schemes 1 and 3). A similar set of reactions also was used to convert L-rhamnose (2) into methyl α-L-mycaroside (21). Attempted synthesis of methyl 2,6-diseoxy-3-C-methyl-a-D-arabino-hexopyranoside (22) (methyl α-D-olivomycosidej from methyl 6-deoxy-3-C-methyl-4-O-(2,2-dimethylpropanoyl)∼2-O-trif lyl-α-D-arabino-hexopyranoside (18), a compound generated during∼synthesis of 20, was thwarted by a methyl migration which produced methyl 2,6-dideoxy-2-C-methyl-α-D-ribo-hexopyranoside (23).This publication has 9 references indexed in Scilit:
- Preparation of methyl 3,6-dideoxy-α-d-xylo-hexopyranoside (methyl α-abequoside) and its α-l-lyxo isomer by reduction of epoxides with lithium triethylborohydrideCarbohydrate Research, 1984
- Regioselective ring opening of selected benzylidene acetals. A photochemically initiated reaction for partial deprotection of carbohydratesThe Journal of Organic Chemistry, 1984
- Chromomycin, mithramycin, and olivomycin binding sites on heterogeneous DNA. Footprinting with methidiumpropyl-EDTA.cntdot.iron(II)Biochemistry, 1983
- Desulfonyloxylations of some secondary p-toluenesulfonates of glycosides by lithium triethylborohydride; a high-yielding route to 2- and 3-deoxy sugarsCarbohydrate Research, 1982
- Synthesen biologisch wichtiger Kohlenhydrate, 241) Derivate des Sibirosamins (4,6‐Didesoxy‐3‐C‐methyl‐4‐methylamino‐D‐altropyranose) durch 4 → 2‐Chiralitätstransfer und vic. cis‐Oxyaminierung eines 3‐C‐Methyl‐hex‐3‐enopyranosidsEuropean Journal of Inorganic Chemistry, 1981
- Synthesen und Reaktionen 3‐C‐methylverzweigter Glycale der D‐Reihe. Darstellungen von Isomeren der endständigen Disaccharide aus Olivomycin A und MithramycinEuropean Journal of Inorganic Chemistry, 1981
- Eine neue Darstellung von Methyl‐α‐ L ‐mycarosidEuropean Journal of Inorganic Chemistry, 1978
- Chromomycin A3, Mithramycin, and Olivomycin: Antitumor Antibiotics of Related StructurePublished by Elsevier ,1975
- The synthesis of L-()-mycarose and L-()-cladinoseTetrahedron, 1962