(4-bromo-1,3-thiazol-2-yl)methanol -Drug Synthesis Database

【结构式】

【分子编号】37948

【品名】(4-bromo-1,3-thiazol-2-yl)methanol

【CA登记号】

【分子式】C₄H₄BrNOS

【分子量】194.0519

【元素组成】C 24.76% H 2.08% Br 41.18% N 7.22% O 8.24% S 16.52%

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：(III)

Lithiation of 2,4-dibromothiazole (I) with n-BuLi at -78 C, followed by condensation with dimethylformamide gave aldehyde (II), which was reduced to alcohol (III) with NaBH4. After protection of the alcohol (III) as the tert-butyldimethylsilyl ether (IV), a second metalation with n-BuLi, and subsequent quenching with tri-n-butyltin chloride furnished stannane (V). Further desilylation of (V) by means of tetrabutylammonium fluoride yielded 2-(hydroxymethyl)-4-(tri-n-butylstannyl)thiazole (VI).

参考文献中间体

合成目标

【1】 Nicolaou, K.C.; et al.; Total synthesis of epothilone E and analogs with modified side chains through the Stille coupling reaction. Angew Chem. Int Ed Engl 1998, 37, 1-2, 84.
【2】 Nicolaou, K.C.; et al.; Total synthesis of epothilone E and related side-chain modified analogues via a stille coupling based strategy. Bioorg Med Chem 1999, 7, 5, 665.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	37946	2,4-dibromo-1,3-thiazole	C₃HBr₂NS	详情	详情
(II)	37947	4-bromo-1,3-thiazole-2-carbaldehyde	C₄H₂BrNOS	详情	详情
(III)	37948	(4-bromo-1,3-thiazol-2-yl)methanol	C₄H₄BrNOS	详情	详情
(IV)	37949	(4-bromo-1,3-thiazol-2-yl)methyl tert-butyl(dimethyl)silyl ether; 4-bromo-2-([[tert-butyl(dimethyl)silyl]oxy]methyl)-1,3-thiazole	C₁₀H₁₈BrNOSSi	详情	详情
(V)	37950	tert-butyl(dimethyl)silyl [4-(tributylstannyl)-1,3-thiazol-2-yl]methyl ether; 2-([[tert-butyl(dimethyl)silyl]oxy]methyl)-4-(tributylstannyl)-1,3-thiazole	C₂₂H₄₅NOSSiSn	详情	详情
(VI)	37951	[4-(tributylstannyl)-1,3-thiazol-2-yl]methanol	C₁₆H₃₁NOSSn	详情	详情

Extended Information