(E)-2-butenyl[bis[(1S,2R,3S,5S)-2,6,6-trimethylbicyclo[3.1.1]hept-3-yl]]borane -Drug Synthesis Database

【结构式】

【分子编号】32426

【品名】(E)-2-butenyl[bis[(1S,2R,3S,5S)-2,6,6-trimethylbicyclo[3.1.1]hept-3-yl]]borane

【CA登记号】

【分子式】C₂₄H₄₁B

【分子量】340.40054

【元素组成】C 84.68% H 12.14% B 3.18%

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：(XIV)

The condensation of (XIII) with the chiral borane (XIV) gives the addition product (XV), which is silylated with TBDMS-OTf affording (XVI). Ozonolysis of the double bond of (XVI) with O3 yields the aldehyde (XVII), which is condensed with TMS-CH2CH=N-t-Bu to provide he unsaturated aldehyde (XVIII).

参考文献中间体

合成目标

【1】 Nicolaou, K.C.; et al.; Total synthesis of sanglifehrin A. Angew Chem. Int Ed Engl 1999, 38, 16, 2447.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
	40677	N-(tert-butyl)-N-[(E)-2-(trimethylsilyl)ethylidene]amine; 2-methyl-N-[(E)-2-(trimethylsilyl)ethylidene]-2-propanamine	C₉H₂₁NSi	详情	详情
(XIII)	32425	2-[(2S,3S,4S,5S,6R,9S,11S)-9-ethyl-3,5,11-trimethyl-8-oxo-4-[(triethylsilyl)oxy]-1-oxa-7-azaspiro[5.5]undec-2-yl]acetaldehyde	C₂₂H₄₁NO₄Si	详情	详情
(XIV)	32426	(E)-2-butenyl[bis[(1S,2R,3S,5S)-2,6,6-trimethylbicyclo[3.1.1]hept-3-yl]]borane	C₂₄H₄₁B	详情	详情
(XV)	32427	(2S,3S,4S,5S,6R,9S,11S)-9-ethyl-2-[(2S,3S)-2-hydroxy-3-methyl-4-pentenyl]-3,5,11-trimethyl-4-[(triethylsilyl)oxy]-1-oxa-7-azaspiro[5.5]undecan-8-one	C₂₆H₄₉NO₄Si	详情	详情
(XVI)	32428	(2S,3S,4S,5S,6R,9S,11S)-2-((2S,3S)-2-[[tert-butyl(dimethyl)silyl]oxy]-3-methyl-4-pentenyl)-9-ethyl-3,5,11-trimethyl-4-[(triethylsilyl)oxy]-1-oxa-7-azaspiro[5.5]undecan-8-one	C₃₂H₆₃NO₄Si₂	详情	详情
(XVII)	32429	(2R,3S)-3-[[tert-butyl(dimethyl)silyl]oxy]-4-[(2S,3S,4S,5S,6R,9S,11S)-9-ethyl-3,5,11-trimethyl-8-oxo-4-[(triethylsilyl)oxy]-1-oxa-7-azaspiro[5.5]undec-2-yl]-2-methylbutanal	C₃₁H₆₁NO₅Si₂	详情	详情
(XVIII)	32430	(E,4S,5S)-5-[[tert-butyl(dimethyl)silyl]oxy]-6-[(2S,3S,4S,5S,6R,9S,11S)-9-ethyl-3,5,11-trimethyl-8-oxo-4-[(triethylsilyl)oxy]-1-oxa-7-azaspiro[5.5]undec-2-yl]-4-methyl-2-hexenal	C₃₃H₆₃NO₅Si₂	详情	详情

Extended Information