TY - JOUR
T1 - Synthesis of 2-O-(3-O-carbamoyl-α-D-mannopyranosyl)-L-gulopyranose
T2 - Sugar moiety of antitumor antibiotic bleomycin
AU - Oshitari, Tetsuta
AU - Shibasaki, Masakatsu
AU - Yoshizawa, Takeshi
AU - Tomita, Masahiro
AU - Takao, Ken Ichi
AU - Kobayashi, Susumu
N1 - Copyright:
Copyright 2007 Elsevier B.V., All rights reserved.
PY - 1997/8/11
Y1 - 1997/8/11
N2 - A new route to the disaccharide moiety (2-O-(3-O-carbamoyl-α-D-mannopyranosyl)-L-gulopyranose) of the antitumor agent bleomycin was developed. 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 acetal methodology. Glycosylation of 21 with 30 proceeded smoothly, and further conversion to disaccharide derivatives (33 and 34) was successfully accomplished.
AB - A new route to the disaccharide moiety (2-O-(3-O-carbamoyl-α-D-mannopyranosyl)-L-gulopyranose) of the antitumor agent bleomycin was developed. 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 acetal methodology. Glycosylation of 21 with 30 proceeded smoothly, and further conversion to disaccharide derivatives (33 and 34) was successfully accomplished.
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U2 - 10.1016/S0040-4020(97)00360-8
DO - 10.1016/S0040-4020(97)00360-8
M3 - Article
AN - SCOPUS:0030798036
SN - 0040-4020
VL - 53
SP - 10993
EP - 11006
JO - Tetrahedron
JF - Tetrahedron
IS - 32
ER -