An efficient synthesis ofα-D-GlcpNAc-(1→2)-[α-D-ManpNAc-(1→3)-]α-L-Rhap-(1→2)-α-L-Rhap-(1→3)-α-L-Rhap(1), the repeating unit of the O10 antigen from Acinetobacter baumannii was achieved via sequenti...An efficient synthesis ofα-D-GlcpNAc-(1→2)-[α-D-ManpNAc-(1→3)-]α-L-Rhap-(1→2)-α-L-Rhap-(1→3)-α-L-Rhap(1), the repeating unit of the O10 antigen from Acinetobacter baumannii was achieved via sequential assembly of the building blocks,p- methoxylphenyl 2,4-di-O-benzoyl-α-L-rhamnopyranoside(2);2-O-allyloxycarbonyl-3,4-di-O-bcnzoyl-α-L-rhamnopyranosyl tri- chloroacetimidate(3);4-methoxylphenyl 3-O-allyloxycarbonyl-4-O-benzoyl-α-L-rhanmopyranoside(4);2-azido-3-O-benzoyl-2- deoxy-4,6-O-isopropylidene-α-D-mannopyranosyl trichloroacetirnidatc(5);2-azido-3,4,6-tri-O-benzoyl-2-deoxy-α,β-D-glucopyr- ano syl trichloroacetimidatc(6).The total yield of 1 from 4 was 4.7%.展开更多
Highly efficient removal of allyloxycarbonyl (Alloc) group was achieved in the presence of CH3COONH4, Pd[P(C6H5)3]4, and NaBH4 in MeOH-THF, within 5 min in almost quantitative yields (〉90%, isolated yield) with...Highly efficient removal of allyloxycarbonyl (Alloc) group was achieved in the presence of CH3COONH4, Pd[P(C6H5)3]4, and NaBH4 in MeOH-THF, within 5 min in almost quantitative yields (〉90%, isolated yield) without affecting acetyl, benzoyl, isopropylidene, benzylidene, allyl, benzyl, benzyl carbonate, or azido groups.展开更多
文摘An efficient synthesis ofα-D-GlcpNAc-(1→2)-[α-D-ManpNAc-(1→3)-]α-L-Rhap-(1→2)-α-L-Rhap-(1→3)-α-L-Rhap(1), the repeating unit of the O10 antigen from Acinetobacter baumannii was achieved via sequential assembly of the building blocks,p- methoxylphenyl 2,4-di-O-benzoyl-α-L-rhamnopyranoside(2);2-O-allyloxycarbonyl-3,4-di-O-bcnzoyl-α-L-rhamnopyranosyl tri- chloroacetimidate(3);4-methoxylphenyl 3-O-allyloxycarbonyl-4-O-benzoyl-α-L-rhanmopyranoside(4);2-azido-3-O-benzoyl-2- deoxy-4,6-O-isopropylidene-α-D-mannopyranosyl trichloroacetirnidatc(5);2-azido-3,4,6-tri-O-benzoyl-2-deoxy-α,β-D-glucopyr- ano syl trichloroacetimidatc(6).The total yield of 1 from 4 was 4.7%.
基金supported by Ph.D.Programs Foundation of Ministry of Education of China,(No.20070019072)the Research Foundation of China Agricultural University(No.90020031).
文摘Highly efficient removal of allyloxycarbonyl (Alloc) group was achieved in the presence of CH3COONH4, Pd[P(C6H5)3]4, and NaBH4 in MeOH-THF, within 5 min in almost quantitative yields (〉90%, isolated yield) without affecting acetyl, benzoyl, isopropylidene, benzylidene, allyl, benzyl, benzyl carbonate, or azido groups.