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【结 构 式】 
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【分子编号】47064 【品名】4-methoxybenzyl 3-[(E)-3-[(2-amino-6-methyl-4-pyrimidinyl)sulfanyl]-1-propenyl]-7-([2-(methoxyimino)-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetyl]amino)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate 【CA登记号】 |
【 分 子 式 】C48H44N8O6S3 【 分 子 量 】925.12568 【元素组成】C 62.32% H 4.79% N 12.11% O 10.38% S 10.4% |
合成路线1
该中间体在本合成路线中的序号：(VIII)Coupling of carboxylic acid (II) to the 7-aminocephem derivative (I) using POCl3 and pyridine produced the corresponding amide (III). Displacement of the chloro group of (III) with triphenyl phosphine furnished the phosphonium salt (IV), which was subjected to a Wittig reaction with chloroacetaldehyde (V), yielding the Z-propenyl chloride (VI). Subsequent reaction of allyl chloride (VI) with 4-amino-2-mercapto-6-methylpyrimidine (VII) in the presence of NaI produced the E-propenyl sulfide (VIII). The N-trityl group and the p-methoxybenzyl ester of (VIII) were finally cleaved by treatment with trifluoroacetic acid in anisole to furnish the title compound.
| 【1】 Lee, C.-S.; et al.; Synthesis and antibacterial activities of novel C(3)-aminopyrimidinyl substituted cephalosporins. J Antibiot 2000, 53, 11, 1305. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 26869 | 4-methoxybenzyl 7-amino-3-(chloromethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate | C16H17ClN2O4S | 详情 | 详情 | |
| (II) | 25058 | 2-(methoxyimino)-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetic acid | 64485-90-1 | C25H21N3O3S | 详情 | 详情 |
| (III) | 25062 | 4-methoxybenzyl 3-(chloromethyl)-7-([2-(methoxyimino)-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetyl]amino)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate | C41H36ClN5O6S2 | 详情 | 详情 | |
| (IV) | 47060 | [[2-[[(4-methoxybenzyl)oxy]carbonyl]-7-([2-(methoxyimino)-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetyl]amino)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl](triphenyl)phosphonium chloride | C59H51ClN5O6PS2 | 详情 | 详情 | |
| (V) | 47061 | 2-chloroacetaldehyde | 107-20-0 | C2H3ClO | 详情 | 详情 |
| (VI) | 47062 | 4-methoxybenzyl 3-[(Z)-3-chloro-1-propenyl]-7-([2-(methoxyimino)-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetyl]amino)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate | C43H38ClN5O6S2 | 详情 | 详情 | |
| (VII) | 47063 | 2-amino-6-methyl-4-pyrimidinethiol; 2-amino-6-methyl-4-pyrimidinylhydrosulfide | C5H7N3S | 详情 | 详情 | |
| (VIII) | 47064 | 4-methoxybenzyl 3-[(E)-3-[(2-amino-6-methyl-4-pyrimidinyl)sulfanyl]-1-propenyl]-7-([2-(methoxyimino)-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetyl]amino)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate | C48H44N8O6S3 | 详情 | 详情 |