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【结 构 式】 
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【分子编号】38598 【品名】benzhydryl (6R,7S)-7-([(E)-[3,5-di(tert-butyl)-4-hydroxyphenyl]methylidene]amino)-3-[[(1-methyl-1H-1,2,3,4-tetraazol-5-yl)sulfanyl]methyl]-8-oxo-5-oxa-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate 【CA登记号】 |
【 分 子 式 】C38H42N6O5S 【 分 子 量 】694.85492 【元素组成】C 65.69% H 6.09% N 12.09% O 11.51% S 4.61% |
合成路线1
该中间体在本合成路线中的序号：(XXI)The reaction of the amino group of (XIX) with 3,5-di-tert-butyl-4-hydroxybenzaldehyde (XX) gives the imine (XXI), which is dehydrogenated with nickel peroxide to the quinomethane (XXII). Addition of methanol to (XXII) yields the 7-alpha-amino compound (XXIII), which is treated with Girard reagent T to afford the 7-beta-amino-7-alpha-methoxyoxacepehem compound (XXIV). The acylation of the NH2 group of (XXIV) with 2-(benzyloxycarbonyl)-2-[4-benzyloxy)phenyl)acetyl chloride (XXV) (obtained by reaction of the corresponding acid (XXVI) with oxalyl chloride) gives the expected amide (XXVII), which is finally deprotected with TFA/anisole or AlCl3/anisole.
| 【1】 Narisada, M.; et al.; Synthetic studies on beta-lactam antibiotics. Part 10. Synthesis of 7beta-[2-carboxy-2-(4-hydroxyphenyl)acetamido]-7alpha-methoxy-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-1-oxa-1-dethia-3-cephem-4-carboxylic acid disodium salt (6059-S) and its related. J Med Chem 1979, 22, 7, 757. |
| 【2】 Nagata, W.; Narisada, M. (Shionogi & Co. Ltd.); Arylmalonamido-1-oxadethiacephalosporins. US 4180571 . |
| 【3】 Narisada, M.; Nagata, W. (Shionogi & Co. Ltd.); Arylmalonamido-1-oxadethiacephalosporins. DE 2713370; US 4138486 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XIX) | 38597 | benzhydryl (6R,7S)-7-amino-3-[[(1-methyl-1H-1,2,3,4-tetraazol-5-yl)sulfanyl]methyl]-8-oxo-5-oxa-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate | C23H22N6O4S | 详情 | 详情 | |
| (XX) | 14875 | 3,5-Bis(1,1-dimethylethyl)-4-hydroxybenzaldehyde; 3,5-di(tert-butyl)-4-hydroxybenzaldehyde; 3,5-Di-tert-butyl-4-hydroxybenzaldehyde | 1620-98-0 | C15H22O2 | 详情 | 详情 |
| (XXI) | 38598 | benzhydryl (6R,7S)-7-([(E)-[3,5-di(tert-butyl)-4-hydroxyphenyl]methylidene]amino)-3-[[(1-methyl-1H-1,2,3,4-tetraazol-5-yl)sulfanyl]methyl]-8-oxo-5-oxa-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate | C38H42N6O5S | 详情 | 详情 | |
| (XXII) | 38599 | benzhydryl (6R)-7-([[3,5-di(tert-butyl)-4-oxo-2,5-cyclohexadien-1-ylidene]methyl]imino)-3-[[(1-methyl-1H-1,2,3,4-tetraazol-5-yl)sulfanyl]methyl]-8-oxo-5-oxa-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate | C38H40N6O5S | 详情 | 详情 | |
| (XXIII) | 38600 | benzhydryl (6R,7R)-7-([(E)-[3,5-di(tert-butyl)-4-hydroxyphenyl]methylidene]amino)-7-methoxy-3-[[(1-methyl-1H-1,2,3,4-tetraazol-5-yl)sulfanyl]methyl]-8-oxo-5-oxa-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate | C39H44N6O6S | 详情 | 详情 | |
| (XXIV) | 38601 | benzhydryl (6R,7R)-7-amino-7-methoxy-3-[[(1-methyl-1H-1,2,3,4-tetraazol-5-yl)sulfanyl]methyl]-8-oxo-5-oxa-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate | 66510-99-4 | C24H24N6O5S | 详情 | 详情 |
| (XXV) | 38602 | benzyl 2-[4-(benzyloxy)phenyl]-3-chloro-3-oxopropanoate | C23H19ClO4 | 详情 | 详情 | |
| (XXVI) | 38603 | 3-(benzyloxy)-2-[4-(benzyloxy)phenyl]-3-oxopropionic acid | C23H20O5 | 详情 | 详情 | |
| (XXVII) | 38604 | benzhydryl (6R,7R)-7-([3-(benzyloxy)-2-[4-(benzyloxy)phenyl]-3-oxopropanoyl]amino)-7-methoxy-3-[[(1-methyl-1H-1,2,3,4-tetraazol-5-yl)sulfanyl]methyl]-8-oxo-5-oxa-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate | C47H42N6O9S | 详情 | 详情 |