(3S,6R,7R,22R,23S,26S,36R,38aR)-7,22-Diacetoxy-28,30,32-triallyloxy-6-[N-(allyloxycarbonyl)-N-methyl-D-leucylamino]-3-(carbamoylmethyl)-10,19-dichloro-44-[3,4,6-tri-O-acetyl-2-O-[3-(allyloxycarbonylamino)-2,3,6,trideoxy-3-C-methyl-beta-L-glucopyranosyloxy]-2,3,4,5,6,7,23,24,25,26,36,37,38,38a-tetradecahydro-1H,22H-8,11:18,21-dietheno-23,36-(iminomethano)-13,16:31,35-dimetheno-[1,6,9]oxadiazacyclohexadecino[4,5-m][10,2,16]benzoxadiazacyclotetracosine-26-carboxylic acid allyl ester; (3S,6R,7R,22R,23S,26S,36R,38aR)-7,22-Diacetoxy-28,30,32-triallyloxy-6-[N-(allyloxycarbonyl)-N-methyl-D-leucylamino]-3-(carbamoylmethyl)-10,19-dichloro-44-[3,4,6-tri-O-acetyl-2-O-[3-(allyloxycarbonylamino)-2,3,6,trideoxy-3-C-methyl-beta-L-glucopyranosyloxy]-2,3,4,5,6,7,23,24,25,26,36,37,38,38a-tetradecahydro-1H,22H-8,11:18,21-dietheno-23,36-(iminomethano)-13,16:31,35-dimetheno-[1,6,9]oxadiazacyclohexadecino[4,5-m][10,2,16]benzoxadiazacyclotetracosine-26-carboxylic acid allyl ester -Drug Synthesis Database

【结构式】

【分子编号】25740

【品名】(3S,6R,7R,22R,23S,26S,36R,38aR)-7,22-Diacetoxy-28,30,32-triallyloxy-6-[N-(allyloxycarbonyl)-N-methyl-D-leucylamino]-3-(carbamoylmethyl)-10,19-dichloro-44-[3,4,6-tri-O-acetyl-2-O-[3-(allyloxycarbonylamino)-2,3,6,trideoxy-3-C-methyl-beta-L-glucopyranosyloxy]-2,3,4,5,6,7,23,24,25,26,36,37,38,38a-tetradecahydro-1H,22H-8,11:18,21-dietheno-23,36-(iminomethano)-13,16:31,35-dimetheno-[1,6,9]oxadiazacyclohexadecino[4,5-m][10,2,16]benzoxadiazacyclotetracosine-26-carboxylic acid allyl ester; (3S,6R,7R,22R,23S,26S,36R,38aR)-7,22-Diacetoxy-28,30,32-triallyloxy-6-[N-(allyloxycarbonyl)-N-methyl-D-leucylamino]-3-(carbamoylmethyl)-10,19-dichloro-44-[3,4,6-tri-O-acetyl-2-O-[3-(allyloxycarbonylamino)-2,3,6,trideoxy-3-C-methyl-beta-L-glucopyranosyloxy]-2,3,4,5,6,7,23,24,25,26,36,37,38,38a-tetradecahydro-1H,22H-8,11:18,21-dietheno-23,36-(iminomethano)-13,16:31,35-dimetheno-[1,6,9]oxadiazacyclohexadecino[4,5-m][10,2,16]benzoxadiazacyclotetracosine-26-carboxylic acid allyl ester

【CA登记号】

【分子式】C₉₆H₁₀₉Cl₂N₉O₃₂

【分子量】1971.86832

【元素组成】C 58.48% H 5.57% Cl 3.6% N 6.39% O 25.96%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(XIV)

Then, the azidobutirate ester of (XI) was selectively removed with PPh3, and the resulting intermediate (XII) was condensed with the protected vancosamine sulfoxide (XIII) to give the protected vancomycin (XIV).

参考文献中间体

合成目标

【1】 Thompson, C.; et al.; Synthesis of vancomycin from the aglycon. J Am Chem Soc 1999, 121, 6, 1237.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(XI)	25737	(3S,6R,7R,22R,23S,26S,36R,38aR)-7,22-Diacetoxy-28,30,32-triallyloxy-6-[N-(allyloxycarbonyl)-N-methyl-D-leucylamino]-3-(carbamoylmethyl)-10,19-dichloro-44-[3,4,6-tri-O-acetyl-6-O-(4-azidobutyryl)-beta-L-glucopyranosyloxy]-2,3,4,5,6,7,23,24,25,26,36,37,38,38a-tetradecahydro-1H,22H-8,11:18,21-dietheno-23,36-(iminomethano)-13,16:31,35-dimetheno-[1,6,9]oxadiazacyclohexadecino[4,5-m][10,2,16]benzoxadiazacyclotetracosine-26-carboxylic acid allyl ester; (3S,6R,7R,22R,23S,26S,36R,38aR)-7,22-Diacetoxy-28,30,32-triallyloxy-6-[N-(allyloxycarbonyl)-N-methyl-D-leucylamino]-3-(carbamoylmethyl)-10,19-dichloro-44-[3,4,6-tri-O-acetyl-6-O-(4-azidobutyryl)-beta-L-glucopyranosyloxy]-2,3,4,5,6,7,23,24,25,26,36,37,38,38a-tetradecahydro-1H,22H-8,11:18,21-dietheno-23,36-(iminomethano)-13,16:31,35-dimetheno-[1,6,9]oxadiazacyclohexadecino[4,5-m][10,2,16]benzoxadiazacyclotetracosine-26-carboxylic acid allyl ester	C₈₈H₉₅Cl₂N₁₁O₃₀	详情	详情
(XII)	25738	(3S,6R,7R,22R,23S,26S,36R,38aR)-7,22-Diacetoxy-28,30,32-triallyloxy-6-[N-(allyloxycarbonyl)-N-methyl-D-leucylamino]-3-(carbamoylmethyl)-10,19-dichloro-44-[3,4,6-tri-O-acetyl-beta-L-glucopyranosyloxy]-2,3,4,5,6,7,23,24,25,26,36,37,38,38a-tetradecahydro-1H,22H-8,11:18,21-dietheno-23,36-(iminomethano)-13,16:31,35-dimetheno-[1,6,9]oxadiazacyclohexadecino[4,5-m][10,2,16]benzoxadiazacyclotetracosine-26-carboxylic acid allyl ester; (3S,6R,7R,22R,23S,26S,36R,38aR)-7,22-Diacetoxy-28,30,32-triallyloxy-6-[N-(allyloxycarbonyl)-N-methyl-D-leucylamino]-3-(carbamoylmethyl)-10,19-dichloro-44-[3,4,6-tri-O-acetyl-beta-L-glucopyranosyloxy]-2,3,4,5,6,7,23,24,25,26,36,37,38,38a-tetradecahydro-1H,22H-8,11:18,21-dietheno-23,36-(iminomethano)-13,16:31,35-dimetheno-[1,6,9]oxadiazacyclohexadecino[4,5-m][10,2,16]benzoxadiazacyclotetracosine-26-carboxylic acid allyl ester	C₈₄H₉₀Cl₂N₈O₂₉	详情	详情
(XIII)	25739	(2S,3S,4S)-4-[[(allyloxy)carbonyl]amino]-2,4-dimethyl-6-(phenylsulfinyl)tetrahydro-2H-pyran-3-yl acetate	C₁₉H₂₅NO₆S	详情	详情
(XIV)	25740	(3S,6R,7R,22R,23S,26S,36R,38aR)-7,22-Diacetoxy-28,30,32-triallyloxy-6-[N-(allyloxycarbonyl)-N-methyl-D-leucylamino]-3-(carbamoylmethyl)-10,19-dichloro-44-[3,4,6-tri-O-acetyl-2-O-[3-(allyloxycarbonylamino)-2,3,6,trideoxy-3-C-methyl-beta-L-glucopyranosyloxy]-2,3,4,5,6,7,23,24,25,26,36,37,38,38a-tetradecahydro-1H,22H-8,11:18,21-dietheno-23,36-(iminomethano)-13,16:31,35-dimetheno-[1,6,9]oxadiazacyclohexadecino[4,5-m][10,2,16]benzoxadiazacyclotetracosine-26-carboxylic acid allyl ester; (3S,6R,7R,22R,23S,26S,36R,38aR)-7,22-Diacetoxy-28,30,32-triallyloxy-6-[N-(allyloxycarbonyl)-N-methyl-D-leucylamino]-3-(carbamoylmethyl)-10,19-dichloro-44-[3,4,6-tri-O-acetyl-2-O-[3-(allyloxycarbonylamino)-2,3,6,trideoxy-3-C-methyl-beta-L-glucopyranosyloxy]-2,3,4,5,6,7,23,24,25,26,36,37,38,38a-tetradecahydro-1H,22H-8,11:18,21-dietheno-23,36-(iminomethano)-13,16:31,35-dimetheno-[1,6,9]oxadiazacyclohexadecino[4,5-m][10,2,16]benzoxadiazacyclotetracosine-26-carboxylic acid allyl ester	C₉₆H₁₀₉Cl₂N₉O₃₂	详情	详情

合成路线2

该中间体在本合成路线中的序号：(XIV)

Subsequent deacetylation with hydrazine produced (XV), from which the allyl and allyloxycarbonyl groups were finally removed by treatment with tributyltin hydride and palladium catalyst.

参考文献中间体

合成目标

【1】 Thompson, C.; et al.; Synthesis of vancomycin from the aglycon. J Am Chem Soc 1999, 121, 6, 1237.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(XIV)	25740	(3S,6R,7R,22R,23S,26S,36R,38aR)-7,22-Diacetoxy-28,30,32-triallyloxy-6-[N-(allyloxycarbonyl)-N-methyl-D-leucylamino]-3-(carbamoylmethyl)-10,19-dichloro-44-[3,4,6-tri-O-acetyl-2-O-[3-(allyloxycarbonylamino)-2,3,6,trideoxy-3-C-methyl-beta-L-glucopyranosyloxy]-2,3,4,5,6,7,23,24,25,26,36,37,38,38a-tetradecahydro-1H,22H-8,11:18,21-dietheno-23,36-(iminomethano)-13,16:31,35-dimetheno-[1,6,9]oxadiazacyclohexadecino[4,5-m][10,2,16]benzoxadiazacyclotetracosine-26-carboxylic acid allyl ester; (3S,6R,7R,22R,23S,26S,36R,38aR)-7,22-Diacetoxy-28,30,32-triallyloxy-6-[N-(allyloxycarbonyl)-N-methyl-D-leucylamino]-3-(carbamoylmethyl)-10,19-dichloro-44-[3,4,6-tri-O-acetyl-2-O-[3-(allyloxycarbonylamino)-2,3,6,trideoxy-3-C-methyl-beta-L-glucopyranosyloxy]-2,3,4,5,6,7,23,24,25,26,36,37,38,38a-tetradecahydro-1H,22H-8,11:18,21-dietheno-23,36-(iminomethano)-13,16:31,35-dimetheno-[1,6,9]oxadiazacyclohexadecino[4,5-m][10,2,16]benzoxadiazacyclotetracosine-26-carboxylic acid allyl ester		C₉₆H₁₀₉Cl₂N₉O₃₂	详情	详情
(XV)	25741	(3S,6R,7R,22R,23S,26S,36R,38aR)-28,30,32-Triallyloxy-6-[N-(allyloxycarbonyl)-N-methyl-D-leucylamino]-44-[2-O-[3-(allyloxycarbonylamino)-2,3,6-trideoxy-3-C-methyl-beta-L-glucopyranosyloxy]-3-(carbamoylmethyl)-10,19-dichloro-7,22-dihyroxy-2,3,4,5,6,7,23,24,25,26,36,37,38,38a-tetradecahydro-1H,22H-8,11:18,21-dietheno-23,36-(iminomethano)-13,16:31,35-dimetheno-[1,6,9]oxadiazacyclohexadecino[4,5-m][10,2,16]benzoxadiazacyclotetracosine-26-carboxylic acid allyl ester; (3S,6R,7R,22R,23S,26S,36R,38aR)-28,30,32-Triallyloxy-6-[N-(allyloxycarbonyl)-N-methyl-D-leucylamino]-44-[2-O-[3-(allyloxycarbonylamino)-2,3,6-trideoxy-3-C-methyl-beta-L-glucopyranosyloxy]-3-(carbamoylmethyl)-10,19-dichloro-7,22-dihyroxy-2,3,4,5,6,7,23,24,25,26,36,37,38,38a-tetradecahydro-1H,22H-8,11:18,21-dietheno-23,36-(iminomethano)-13,16:31,35-dimetheno-[1,6,9]oxadiazacyclohexadecino[4,5-m][10,2,16]benzoxadiazacyclotetracosine-26-carboxylic acid allyl ester		C₈₅H₉₇Cl₂N₉O₂₈	详情	详情

Extended Information