TY - JOUR
T1 - Donor-bound glycosylation for various glycosyl acceptors
T2 - Bidirectional solid-phase semisynthesis of vancomycin and its derivatives
AU - Doi, Takayuki
AU - Kinbara, Atsushi
AU - Inoue, Hitoshi
AU - Takahashi, Takashi
PY - 2007
Y1 - 2007
N2 - The glycosidation of a polymer-supported glycosyl donor. N-phenyltrifluoroacetimidate, with various glycosyl acceptors is reported. The application of the polymer-supported N-phenyltrifluoroacetimidate is demonstrated in the synthesis of vancomycin derivatives. 2-O-[2-(azidomethyl) benzoyl]glycosyl imidate was attached to a polymer support at the 6-position by a phenylsulfonate linked with a C13 alkyl spacer. Solid-phase glycosidation with a vancomycin aglycon, selective deprotection of the 2-(azidomethyl)-benzoyl group, and glycosylation of the resulting 2-hydroxy group with a vancosamine unit were performed. Nucleophilic cleavage from the polymer support with acetate, chloride, azido, and thioacetate ions provided vancomycin derivatives in pure form after simple purification. The semisynthesis of vancomycin was achieved by deprotection of the acetate derivative.
AB - The glycosidation of a polymer-supported glycosyl donor. N-phenyltrifluoroacetimidate, with various glycosyl acceptors is reported. The application of the polymer-supported N-phenyltrifluoroacetimidate is demonstrated in the synthesis of vancomycin derivatives. 2-O-[2-(azidomethyl) benzoyl]glycosyl imidate was attached to a polymer support at the 6-position by a phenylsulfonate linked with a C13 alkyl spacer. Solid-phase glycosidation with a vancomycin aglycon, selective deprotection of the 2-(azidomethyl)-benzoyl group, and glycosylation of the resulting 2-hydroxy group with a vancosamine unit were performed. Nucleophilic cleavage from the polymer support with acetate, chloride, azido, and thioacetate ions provided vancomycin derivatives in pure form after simple purification. The semisynthesis of vancomycin was achieved by deprotection of the acetate derivative.
KW - Antibiotics
KW - Glycopeptides
KW - Glycosylation
KW - Solid-phase synthesis
KW - Vancomycin
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U2 - 10.1002/asia.200600301
DO - 10.1002/asia.200600301
M3 - Article
C2 - 17441153
AN - SCOPUS:33846266192
VL - 2
SP - 188
EP - 198
JO - Chemistry - An Asian Journal
JF - Chemistry - An Asian Journal
SN - 1861-4728
IS - 1
ER -