[Synthetic studies of polyene macrolide antibiotics. 3. Hydrogenation of methyl-6-deoxy-2,3-O-isopropylidene-4-methylene- alpha-L-lyxo-hexopyranoside].
Experimental conditions of hydrogenation of the title compound are found (excess of Raney catalyst in benzene solution, 5 degrees C, 2h) to afford methyl 4,6-dideoxy-2,3-O-isopropylidene-4-C-methyl-alpha-L-mannopyranoside, the key intermediate in the synthesis of C33-C38 fragment of amphotericin B, with the yield as high as 57%.
Romanovich
A Iu
AIu
Chizhov
O S
OS
Sviridov
A F
AF
D000666:Amphotericin B / Q000138:chemical synthesis*; D055598:Chemical Phenomena; D002621:Chemistry; D006865:Hydrogenation; D008759:Methylglycosides / Q000138:chemical synthesis*; D011090:Polyenes / Q000138:chemical synthesis; D013237:Stereoisomerism
D008759:Methylglycosides; D011090:Polyenes; C055813:methyl-6-deoxy-2,3-isopropylidene-4-methylene lyxo-pyranoside; D000666:Amphotericin B
Sinteticheskie issledovaniia v riadu polienovykh makrolidnykh antibiotikov. 3. Gidrirovanie metil-6-dezoksi-2,3-O- izopropiliden-4-metilen-alpha-L-likso-geksopiranozida.