(1R,2S)-1-ethyl-2-[(heptyloxy)methoxy]propyl 4-bromobenzenesulfonate -Drug Synthesis Database

【结构式】

【分子编号】17074

【品名】(1R,2S)-1-ethyl-2-[(heptyloxy)methoxy]propyl 4-bromobenzenesulfonate

【CA登记号】

【分子式】C₁₉H₃₁BrO₅S

【分子量】451.42214

【元素组成】C 50.55% H 6.92% Br 17.7% O 17.72% S 7.1%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(XXI)

The bromosulfonate (XXI) has been obtained as follows: (S)-Lactic acid methyl ester (XXII) has been protected as its benzyloxymethyl ether (XXIII) according to Tetrahedron Lett 1980, 21: 1035. The reduction of (XXIII) with DIBAL yields the corresponding aldehyde (XXIV), which by a Grignard reaction with ethylmagnesium bromide in THF and chromatographic separation of the diastereoisomers (SiO2, hexane/ethyl acetate) affords 2(S)-(benzyloxymethoxy)-3(R)-pentanol (XXV). Finally, this compound is sulfonated to (XXI) with 4-bromobenzenesulfonyl chloride. Finally, compound (XX) is condensed with 2(S)-(benzyloxymethoxy)-3(R)-pentanol 4-bromobenzenesulfonate ester (XXI) by means of cesium carbonate in DMF, and deprotected with 6N HCl.

参考文献中间体

合成目标

【1】 Fromtling, R.A.; Castañer, J.; SCH-56592. Drugs Fut 1996, 21, 2, 160.
【2】 Saksena, A.K.; Girijavallabhan, V.M.; Lovey, R.G.; Pike, R.E.; Wang, H.; Liu, Y.-T.; Ganguly, A.K.; Bennett, F. (Schering Corp.); Tetrahydrofuran antifungals. EP 0736030; JP 1997500658; US 5661151; US 5703079; WO 9517407 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
	18964	4-bromobenzenesulfonyl chloride	98-58-8	C₆H₄BrClO₂S	详情	详情
(XX)	16351	4-[4-[4-(4-[[(3R,5R)-5-(2,4-difluorophenyl)-5-(1H-1,2,4-triazol-1-ylmethyl)tetrahydro-3-furanyl]methoxy]phenyl)-1-piperazinyl]phenyl]-2,4-dihydro-3H-1,2,4-triazol-3-one		C₃₂H₃₂F₂N₈O₃	详情	详情
(XXI)	17074	(1R,2S)-1-ethyl-2-[(heptyloxy)methoxy]propyl 4-bromobenzenesulfonate		C₁₉H₃₁BrO₅S	详情	详情
(XXII)	17075	propionic acid, 2-hydroxy-, methyl ester, (S)-; methyl (2S)-2-hydroxypropanoate	27871-49-4	C₄H₈O₃	详情	详情
(XXIII)	17076	methyl (2S)-2-[(heptyloxy)methoxy]propanoate		C₁₂H₂₄O₄	详情	详情
(XXIV)	17077	(2S)-2-[(heptyloxy)methoxy]propanal		C₁₁H₂₂O₃	详情	详情
(XXV)	17078	(2S,3R)-2-[(heptyloxy)methoxy]-3-pentanol		C₁₃H₂₈O₃	详情	详情

合成路线2

该中间体在本合成路线中的序号：(V)

参考文献中间体

合成目标

【1】 Bennett F, Sakasena AK, Lovey R, et al. 2006. Hydroxylated analogues of the orally active broad spectrum antifungal, Sch 51048, and the discovery of posaconazole(Sch 56592) . Bioorg Med Chem Lett, 16, 186～190

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)	17075	propionic acid, 2-hydroxy-, methyl ester, (S)-; methyl (2S)-2-hydroxypropanoate	27871-49-4	C₄H₈O₃	详情	详情
(II)	17076	methyl (2S)-2-[(heptyloxy)methoxy]propanoate		C₁₂H₂₄O₄	详情	详情
(III)	17077	(2S)-2-[(heptyloxy)methoxy]propanal		C₁₁H₂₂O₃	详情	详情
(IV)	17078	(2S,3R)-2-[(heptyloxy)methoxy]-3-pentanol		C₁₃H₂₈O₃	详情	详情
(V)	17074	(1R,2S)-1-ethyl-2-[(heptyloxy)methoxy]propyl 4-bromobenzenesulfonate		C₁₉H₃₁BrO₅S	详情	详情
(VI)	16351	4-[4-[4-(4-[[(3R,5R)-5-(2,4-difluorophenyl)-5-(1H-1,2,4-triazol-1-ylmethyl)tetrahydro-3-furanyl]methoxy]phenyl)-1-piperazinyl]phenyl]-2,4-dihydro-3H-1,2,4-triazol-3-one		C₃₂H₃₂F₂N₈O₃	详情	详情

Extended Information