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【结 构 式】

【分子编号】43139

【品名】 

【CA登记号】

【 分 子 式 】C19H18O3S3

【 分 子 量 】390.54812

【元素组成】C 58.43% H 4.65% O 12.29% S 24.63%

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:(XI)

In an alternative procedure, the bithiophene aldehyde (II) was reduced to alcohol (VII) with NaBH4, and this was protected with dihydropyran to give (VIII). Lithiation and subsequent treatment of (VIII) with tributyltin chloride afforded the stannyl compound (IX). This was then coupled with 2-bromo-4-thiophene-carboxaldehyde (X) in the presence of Pd(PPh3)4 and an additional amount of PPh3 to provide the terthiophene (XI). The reduction of the aldehyde group of (XI) with NaBH4, and then acid hydrolysis of the tetrahydropyranyl protecting group furnished diol (XII). Finally, the oxidation of (XII) by means of DDQ gave rise to a 1:3 mixture of the desired hydroxy aldehyde and its regioisomer (XIII).

1 Xu, W.-C.; Chang, C.-j.; Zhou, Q.; Ashendel, C.L.; Chang, C.t.; Novel protein kinase C inhibitors: Synthesis and PKC inhibition of beta-substituted polythiophene derivatives. Bioorg Med Chem Lett 1999, 9, 15, 2279.
2 Chang, C.-T.; Chang, C.-J.; Lee, C.-T.; Lin, F.-L.; Tsai, J.-D.; Ashendel, C.L.; Chan, T.C.K.; Geahlen, R.L.; Waters, D.J. (Industrial Technology & Research Institute; Purdue Research Foundation); Polythiophene anti-tumor agents. EP 1007035; WO 9823269 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(II) 43131 2,2'-Bithienyl-5-carboxaldehyde 2,2'-Bithienyl-5-carboxaldehyde 2,2'-Bithienyl-5-carboxaldehyde 3779-27-9 C9H6OS2 详情 详情
(VII) 43136 2,2'-Bithien-5-ylmethanol 3515-30-8 C9H8OS2 详情 详情
(VIII) 43137   C14H16O2S2 详情 详情
(IX) 43138   C26H42O2S2Sn 详情 详情
(X) 31660 5-bromo-3-thiophenecarbaldehyde C5H3BrOS 详情 详情
(XI) 43139   C19H18O3S3 详情 详情
(XII) 43140   C14H12O2S3 详情 详情
(XIII) 43141   C14H10O2S3 详情 详情
Extended Information