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【结 构 式】

【分子编号】52088

【品名】ethyl (2S,3R)-2,3-dihydroxybutanoate

【CA登记号】

【 分 子 式 】C6H12O4

【 分 子 量 】148.15888

【元素组成】C 48.64% H 8.16% O 43.2%

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:(II)

The title compound was isolated from the fermentation broth of Streptomyces sp. strain HC-21. A synthetic method for the preparation of the title compound was also reported. Asymmetric dihydroxylation of ethyl crotonate (I) using commercial AD-mix-beta produced diol (II). This was converted to the (2S,3R)-epoxide (III) by bromination with HBr in HOAc followed by cyclization of the resultant bromohydrin in the presence of DBU. Epoxide ring opening with the organomagnesium reagent generated from indole (IV) and methylmagnesium bromide furnished the chiral indolylbutanoate (V). Cyclization of the hydroxy ester (V) with guanidine hydrochloride (VI) in the presence of potassium tert-butoxide yielded the amino oxazolone (VII). Finally, displacement of the amino- by a methylamino group was achieved by treatment with aqueous methylamine.

1 Kanamaru, T.; Nakao, M.; Tawada, H.; Kamiyama, K. (Takeda Chemical Industries, Ltd.); Oxazolone derivs. and their use as anti-Helicobacter pylori agent. EP 0923577; JP 1998279579; US 6169102; WO 9749703 .
2 Kamiyama, K.; Nakayama, Y. (Takeda Chemical Industries, Ltd.); Process for producing indolmycins. WO 9952905 .
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) 52087 Ethyl crotonate; trans-Ethyl crotonate; Crotonic acid ethyl ester 623-70-1 C6H10O2 详情 详情
(II) 52088 ethyl (2S,3R)-2,3-dihydroxybutanoate C6H12O4 详情 详情
(III) 52089 ethyl (2S,3R)-3-methyl-2-oxiranecarboxylate C6H10O3 详情 详情
(IV) 15292 Indole; 1H-indole 120-72-9 C8H7N 详情 详情
(V) 52090 ethyl (2S,3R)-2-hydroxy-3-(1H-indol-3-yl)butanoate C14H17NO3 详情 详情
(VI) 14790 Guanidine 113-00-8 CH5N3 详情 详情
(VII) 52091 (5S)-2-amino-5-[(1R)-1-(1H-indol-3-yl)ethyl]-1,3-oxazol-4(5H)-one C13H13N3O2 详情 详情
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