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【结 构 式】

【分子编号】39548

【品名】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

【CA登记号】

【 分 子 式 】C27H30N6O6S

【 分 子 量 】566.63804

【元素组成】C 57.23% H 5.34% N 14.83% O 16.94% S 5.66%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(VIII)

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
Extended Information