(1Z,3Z)-1-bromo-1,3-hexadiene -Drug Synthesis Database

【结构式】

【分子编号】58209

【品名】(1Z,3Z)-1-bromo-1,3-hexadiene

【CA登记号】

【分子式】C₆H₉Br

【分子量】161.04146

【元素组成】C 44.75% H 5.63% Br 49.62%

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：(XXVI)

The reaction of the dihydroxy compound (XX) with Tbdms-Cl and imidazole gives the disilylated compound (XXI), which is deallylated by means of Pd(PPh3)4 to yield the 2-butenoic acid derivative (XXII). The reaction of (XXII) with the phosphoryl azide (XXIII) by means of TEA in benzene affords the butenoyl azide (XXIV), which is converted into the isocyanate (XXV) by heating in refluxing benzene. The reaction of (XXV) with 1,3-hexadienyl bromide (XXVI) by means of t-BuLi in THF provides the 2,4-heptadienoyl amide (XXVII), which is finally desilylated by means of HF and pyridine in THF to obtain the target Salicylihalamide A.

参考文献中间体

合成目标

【1】 Xie, X.-S.; De Brabander, J.K.; Wang, R.; Liao, X.; Wu, Y.; Total synthesis and initial structure-function analysis of the potent V-ATPase inhibitors salicylihalamide A and related compounds. J Am Chem Soc 2002, 124, 13, 3245.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(XX)	58203		C₂₃H₂₆O₆	详情	详情
(XXI)	58204		C₃₅H₅₄O₆Si₂	详情	详情
(XXII)	58205	(E)-4-((2S,4R,5S)-4,14-bis{[tert-butyl(dimethyl)silyl]oxy}-5-methyl-16-oxooxa-7,8,11,13-cyclohexadecatetraen-2-yl)-2-butenoic acid	C₃₂H₅₄O₆Si₂	详情	详情
(XXIII)	58206		C₁₂H₁₀N₃O₃P	详情	详情
(XXIV)	58207	(E)-4-((2S,4R,5S)-4,14-bis{[tert-butyl(dimethyl)silyl]oxy}-5-methyl-16-oxooxa-7,8,11,13-cyclohexadecatetraen-2-yl)-2-butenoyl azide	C₃₂H₅₃N₃O₅Si₂	详情	详情
(XXV)	58208	(13S,14R,16S)-4,14-bis{[tert-butyl(dimethyl)silyl]oxy}-16-[(E)-3-isocyanato-2-propenyl]-13-methyloxa-4,6,9,10-cyclohexadecatetraen-2-one	C₃₂H₅₃NO₅Si₂	详情	详情
(XXVI)	58209	(1Z,3Z)-1-bromo-1,3-hexadiene	C₆H₉Br	详情	详情
(XXVII)	58210	(2Z,4Z)-N-[(E)-3-((2S,4R,5S)-4,14-bis{[tert-butyl(dimethyl)silyl]oxy}-5-methyl-16-oxooxa-7,8,11,13-cyclohexadecatetraen-2-yl)-1-propenyl]-2,4-heptadienamide	C₃₈H₆₃NO₅Si₂	详情	详情

Extended Information