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【结 构 式】

【分子编号】63908

【品名】dipropyl (2-methyl-1,3-thiazol-4-yl)methylphosphonate

【CA登记号】

【 分 子 式 】C11H20NO3PS

【 分 子 量 】277.324502

【元素组成】C 47.64% H 7.27% N 5.05% O 17.31% P 11.17% S 11.56%

与该中间体有关的原料药合成路线共 2 条

合成路线1

该中间体在本合成路线中的序号:(X)

The intermediate phosphonate (X) has been obtained as follows. The cyclization of thioacetamide (IV) with ethyl 3-bromopiruvate (V) in ethanol gives 2-methylthiazole-4-carboxylic acid ethyl ester (VI), which is reduced by means of LiAlH4 in ethyl ether to yield the carbinol (VII). The bromination of (VII) with CBr4 and PPh3 in CCl4 affords the 4-bromomethyl-2-methylthiazole (VIII), which is finally condensed with triethyl phosphite (IX) to provide the target phosphonate intermediate (X). Alternatively, the cyclization of thioacetamide (IV) with 1,3-dichloroacetone (XI) gives 4-(chloromethyl)-2-methylthiazole (XII), which is condensed with triethyl phosphite (IX) to also provide the target phosphonate intermediate (X).

1 Jung, J.-K.; Kache, R.; Vines, K.K.; Zheng, Y.-S.; Avery, M.A.; Total synthesis of epothilones B and D amenable to large-scale preparation. 225th ACS Natl Meet (March 23 2003, New Orleans) 2003, Abst MEDI 121.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(IV) 19170 ethanethioamide 62-55-5 C2H5NS 详情 详情
(V) 63904 propyl 3-bromo-2-oxopropanoate C6H9BrO3 详情 详情
(VI) 63905 propyl 2-methyl-1,3-thiazole-4-carboxylate C8H11NO2S 详情 详情
(VII) 63906 (2-methyl-1,3-thiazol-4-yl)methanol C5H7NOS 详情 详情
(VIII) 63909 4-(bromomethyl)-2-methyl-1,3-thiazole C5H6BrNS 详情 详情
(IX) 15487 triethyl phosphite 122-52-1 C6H15O3P 详情 详情
(X) 63908 dipropyl (2-methyl-1,3-thiazol-4-yl)methylphosphonate C11H20NO3PS 详情 详情
(XI) 63907 1,3-dichloroacetone C3H4Cl2O 详情 详情
(XII) 40819 4-(chloromethyl)-2-methyl-1,3-thiazole C5H6ClNS 详情 详情

合成路线2

该中间体在本合成路线中的序号:(X)

The intermediate phosphonate (X) has been obtained as follows. The cyclization of thioacetamide (IV) with ethyl 3-bromopiruvate (V) in ethanol gives 2-methylthiazole-4-carboxylic acid ethyl ester (VI), which is reduced by means of LiAlH4 in ethyl ether to yield the carbinol (VII). The bromination of (VII) with CBr4 and PPh3 in CCl4 affords the 4-bromomethyl-2-methylthiazole (VIII), which is finally condensed with triethyl phosphite (IX) to provide the target phosphonate intermediate (X). Alternatively, the cyclization of thioacetamide (IV) with 1,3-dichloroacetone (XI) gives 4-(chloromethyl)-2-methylthiazole (XII), which is condensed with triethyl phosphite (IX) to also provide the target phosphonate intermediate (X).

1 Jung, J.-K.; Kache, R.; Vines, K.K.; Zheng, Y.-S.; Avery, M.A.; Total synthesis of epothilones B and D amenable to large-scale preparation. 225th ACS Natl Meet (March 23 2003, New Orleans) 2003, Abst MEDI 121.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(IV) 19170 ethanethioamide 62-55-5 C2H5NS 详情 详情
(V) 63904 propyl 3-bromo-2-oxopropanoate C6H9BrO3 详情 详情
(VI) 63905 propyl 2-methyl-1,3-thiazole-4-carboxylate C8H11NO2S 详情 详情
(VII) 63906 (2-methyl-1,3-thiazol-4-yl)methanol C5H7NOS 详情 详情
(VIII) 63909 4-(bromomethyl)-2-methyl-1,3-thiazole C5H6BrNS 详情 详情
(IX) 15487 triethyl phosphite 122-52-1 C6H15O3P 详情 详情
(X) 63908 dipropyl (2-methyl-1,3-thiazol-4-yl)methylphosphonate C11H20NO3PS 详情 详情
(XI) 63907 1,3-dichloroacetone C3H4Cl2O 详情 详情
(XII) 40819 4-(chloromethyl)-2-methyl-1,3-thiazole C5H6ClNS 详情 详情
Extended Information