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【结 构 式】 
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【分子编号】39546 【品名】benzhydryl 2-((2R,3R)-3-(benzoylamino)-2-[2-hydroxy-3-[(1-methyl-1H-1,2,3,4-tetraazol-5-yl)sulfanyl]propoxy]-3-methoxy-4-oxoazetidinyl)-3-methyl-2-butenoate 【CA登记号】 |
【 分 子 式 】C34H36N6O7S 【 分 子 量 】672.76208 【元素组成】C 60.7% H 5.39% N 12.49% O 16.65% S 4.77% |
合成路线1
该中间体在本合成路线中的序号：(VI)The epoxidation of alpha-(3beta-benzamido-4beta-allyloxy-2-oxoazetidin-1-yl)-alpha-isopropylilideneacetic acid diphenylmethyl ester (I) with a peracid gives the corresponding epoxide in the allyl group (II), which is chlorinated with tert-butyl hypochlorite affording the chloro epoxide (III). The methoxylation of (III) with lithium methoxide yields the 3beta-benzamido-3alpha-methoxy derivative (IV), which is condensed with lithium 1-methyltetrazol-5-ylmercaptide (V) to afford the tetrazol derivative (VI). The oxidation of (VI) with CrO3 affords the ketonic compound (VII), which is debenzoylated by treatment with PCl5, MeOH and triethylamine giving alpha-[3beta-amino-3alpha-methoxy-4beta-[3-(1-methyltetrazol-5-yl)thiomethyl-2-oxopropoxy]-2-oxoazetidine-1-yl]-alpha-isopropylidieneacetic acid diphenylmethyl ester (VIII). The condensation of (VIII) with alpha-(p-benzyloxyphenyl)-alpha-(benzyloxycarbonyl)acetyl chloride (IX) by means of triethylamine affords the 3beta-[alpha-(benzyloxyphenyl)-alpha-(benzyloxycarbonyl)acetamido] derivative (XX).
| 【1】 Serradell, M.N.; Blancafort, P.; Castaner, J.; S-6059. Drugs Fut 1979, 4, 9, 667. |
| 【2】 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 |
|---|---|---|---|---|---|---|
| (I) | 39541 | benzhydryl 2-[(2R,3S)-2-(allyloxy)-3-(benzoylamino)-4-oxoazetidinyl]-3-methyl-2-butenoate | C31H30N2O5 | 详情 | 详情 | |
| (II) | 39542 | benzhydryl 2-[(2R,3S)-3-(benzoylamino)-2-(2-oxiranylmethoxy)-4-oxoazetidinyl]-3-methyl-2-butenoate | C31H30N2O6 | 详情 | 详情 | |
| (III) | 39543 | benzhydryl 2-[(2R,3R)-3-(benzoylamino)-3-chloro-2-(2-oxiranylmethoxy)-4-oxoazetidinyl]-3-methyl-2-butenoate | C31H29ClN2O6 | 详情 | 详情 | |
| (IV) | 39544 | benzhydryl 2-[(2R,3R)-3-(benzoylamino)-3-methoxy-2-(2-oxiranylmethoxy)-4-oxoazetidinyl]-3-methyl-2-butenoate | C32H32N2O7 | 详情 | 详情 | |
| (V) | 39545 | C2H4LiN4S | 详情 | 详情 | ||
| (VI) | 39546 | benzhydryl 2-((2R,3R)-3-(benzoylamino)-2-[2-hydroxy-3-[(1-methyl-1H-1,2,3,4-tetraazol-5-yl)sulfanyl]propoxy]-3-methoxy-4-oxoazetidinyl)-3-methyl-2-butenoate | C34H36N6O7S | 详情 | 详情 | |
| (VII) | 39547 | benzhydryl 2-((2R,3R)-3-(benzoylamino)-3-methoxy-2-[3-[(1-methyl-1H-1,2,3,4-tetraazol-5-yl)sulfanyl]-2-oxopropoxy]-4-oxoazetidinyl)-3-methyl-2-butenoate | C34H34N6O7S | 详情 | 详情 | |
| (VIII) | 39548 | benzhydryl 2-((2R,3R)-3-amino-3-methoxy-2-[3-[(1-methyl-1H-1,2,3,4-tetraazol-5-yl)sulfanyl]-2-oxopropoxy]-4-oxoazetidinyl)-3-methyl-2-butenoate | C27H30N6O6S | 详情 | 详情 | |
| (IX) | 38602 | benzyl 2-[4-(benzyloxy)phenyl]-3-chloro-3-oxopropanoate | C23H19ClO4 | 详情 | 详情 | |
| (X) | 39549 | benzhydryl 2-((2R,3R)-3-([3-(benzyloxy)-2-[4-(benzyloxy)phenyl]-3-oxopropanoyl]amino)-3-methoxy-2-[3-[(1-methyl-1H-1,2,3,4-tetraazol-5-yl)sulfanyl]-2-oxopropoxy]-4-oxoazetidinyl)-3-methyl-2-butenoate | C50H48N6O10S | 详情 | 详情 |