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【结 构 式】 
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【分子编号】25734 【品名】allyl (1S,2R,18R,19R,22S,25R,28R,40R)-32,37-bis(allyloxy)-19-([(2R)-2-[[(allyloxy)carbonyl](methyl)amino]-4-methylpentanoyl]amino)-22-(2-amino-2-oxoethyl)-5,15-dichloro-2,18-dihydroxy-50-[(4-methoxybenzyl)oxy]-20,23,26,42,44-pentaoxo-35-(vinyloxy)-7,13-dioxa-21,24,27,41,43-pentaazaoctacyclo[26.14.2.2(3,6).2(14,17).1(8,12).1(29,33).0(10,25).0(34,39)]pentaconta-3,5,8(50),9,11,14,16,29(49),30,32,34,36,38,45,47-pentadecaene-40-carboxylate 【CA登记号】 |
【 分 子 式 】C76H78Cl2N8O20 【 分 子 量 】1494.40264 【元素组成】C 61.08% H 5.26% Cl 4.74% N 7.5% O 21.41% |
合成路线1
该中间体在本合成路线中的序号：(VIII)Selective protection of the phenol group of (V) with p-methoxybenzyl chloride (VI) gave benzyl ether (VII), and the remaining phenol groups of (VII) were further alkylated with allyl bromide to afford (VIII).
| 【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 |
|---|---|---|---|---|---|---|
| (IV) | 11463 | 3-Bromo-1-propene; 3-Bromopropene；allyl bromide | 106-95-6 | C3H5Br | 详情 | 详情 |
| (V) | 25732 | allyl (1S,2R,18R,19R,22S,25R,28R,40R)-19-([(2R)-2-[[(allyloxy)carbonyl](methyl)amino]-4-methylpentanoyl]amino)-22-(2-amino-2-oxoethyl)-5,15-dichloro-2,18,32,35,37,50-hexahydroxy-20,23,26,42,44-pentaoxo-7,13-dioxa-21,24,27,41,43-pentaazaoctacyclo[26.14.2.2(3,6).2(14,17).1(8,12).1(29,33).0(10,25).0(34,39)]pentaconta-3,5,8(50),9,11,14,16,29(49),30,32,34,36,38,45,47-pentadecaene-40-carboxylate | C60H60Cl2N8O19 | 详情 | 详情 | |
| (VI) | 11910 | 4-Methoxybenzyl chloride; 1-(Chloromethyl)-4-methoxybenzene; alpha-Chloro-4-methoxytoluene; 4-(Chloromethyl)phenyl methyl ether | 824-94-2 | C8H9ClO | 详情 | 详情 |
| (VII) | 25733 | allyl (1S,2R,18R,19R,22S,25R,28R,40R)-19-([(2R)-2-[[(allyloxy)carbonyl](methyl)amino]-4-methylpentanoyl]amino)-22-(2-amino-2-oxoethyl)-5,15-dichloro-2,18,32,35,37-pentahydroxy-50-[(4-methoxybenzyl)oxy]-20,23,26,42,44-pentaoxo-7,13-dioxa-21,24,27,41,43-pentaazaoctacyclo[26.14.2.2(3,6).2(14,17).1(8,12).1(29,33).0(10,25).0(34,39)]pentaconta-3,5,8(50),9,11,14,16,29(49),30,32,34,36,38,45,47-pentadecaene-40-carboxylate | C68H68Cl2N8O20 | 详情 | 详情 | |
| (VIII) | 25734 | allyl (1S,2R,18R,19R,22S,25R,28R,40R)-32,37-bis(allyloxy)-19-([(2R)-2-[[(allyloxy)carbonyl](methyl)amino]-4-methylpentanoyl]amino)-22-(2-amino-2-oxoethyl)-5,15-dichloro-2,18-dihydroxy-50-[(4-methoxybenzyl)oxy]-20,23,26,42,44-pentaoxo-35-(vinyloxy)-7,13-dioxa-21,24,27,41,43-pentaazaoctacyclo[26.14.2.2(3,6).2(14,17).1(8,12).1(29,33).0(10,25).0(34,39)]pentaconta-3,5,8(50),9,11,14,16,29(49),30,32,34,36,38,45,47-pentadecaene-40-carboxylate | C76H78Cl2N8O20 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(VIII)After acetylation of the benzylic alcohols of (VIII), deprotection of the p-methoxybenzyl group with TFA furnished the protected aglycon (IX). Glycosylation with the protected glucopyranose sulfoxide (X) was effected in the presence of triflic anhydride, 2,6-di-tert-butyl-4-methylpyridine, and boron trifluoride etherate to produce (XI).
| 【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 |
|---|---|---|---|---|---|---|
| (VIII) | 25734 | allyl (1S,2R,18R,19R,22S,25R,28R,40R)-32,37-bis(allyloxy)-19-([(2R)-2-[[(allyloxy)carbonyl](methyl)amino]-4-methylpentanoyl]amino)-22-(2-amino-2-oxoethyl)-5,15-dichloro-2,18-dihydroxy-50-[(4-methoxybenzyl)oxy]-20,23,26,42,44-pentaoxo-35-(vinyloxy)-7,13-dioxa-21,24,27,41,43-pentaazaoctacyclo[26.14.2.2(3,6).2(14,17).1(8,12).1(29,33).0(10,25).0(34,39)]pentaconta-3,5,8(50),9,11,14,16,29(49),30,32,34,36,38,45,47-pentadecaene-40-carboxylate | C76H78Cl2N8O20 | 详情 | 详情 | |
| (IX) | 25735 | allyl (1S,2R,18R,19R,22S,25R,28R,40R)-2,18-bis(acetoxy)-32,37-bis(allyloxy)-19-([(2R)-2-[[(allyloxy)carbonyl](methyl)amino]-4-methylpentanoyl]amino)-22-(2-amino-2-oxoethyl)-5,15-dichloro-50-hydroxy-20,23,26,42,44-pentaoxo-35-(vinyloxy)-7,13-dioxa-21,24,27,41,43-pentaazaoctacyclo[26.14.2.2(3,6).2(14,17).1(8,12).1(29,33).0(10,25).0(34,39)]pentaconta-3,5,8(50),9,11,14,16,29(49),30,32,34,36,38,45,47-pentadecaene-40-carboxylate | C72H74Cl2N8O21 | 详情 | 详情 | |
| (X) | 25736 | (2R,3S,4R,5R,6S)-4,5-bis(acetoxy)-6-[(acetoxy)methyl]-2-(phenylsulfinyl)tetrahydro-2H-pyran-3-yl 4-azidobutanoate | C22H27N3O10S | 详情 | 详情 | |
| (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 |