(3R,4S)-1-[[tert-butyl(dimethyl)silyl]oxy]-4-methyl-5-hexen-3-ol -Drug Synthesis Database

【结构式】

【分子编号】50354

【品名】(3R,4S)-1-[[tert-butyl(dimethyl)silyl]oxy]-4-methyl-5-hexen-3-ol

【CA登记号】

【分子式】C₁₃H₂₈O₂Si

【分子量】244.44962

【元素组成】C 63.88% H 11.55% O 13.09% Si 11.49%

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：(XXXV)

The condensation of 3-(tert-butyldimethylsilyloxy)propanal (XXXIII) with the chiral borane (XXXIV) by means of H2O2 and NaHCO3 gives the chiral alcohol (XXXV), which is oxidized with OsO4 and NaIO4 to yield the aldehyde (XXXVI). The Wittig condensation of (XXXVI) with phosphorane (XVI) affords the heptenoic ester (XXXVII), which is reduced with H2 over Pd/C to provide the saturated hydroxy ester (XXXVIII). The cyclization of (XXXVIII) by means of PPTS in refluxing dichloromethane gives the lactone (XXXIX), which by reaction with Cp2TiMe2 yields the methylene derivative (I).

参考文献中间体

合成目标

【1】 Guzzupe, A.N.; et al.; Total synthesis of the epidermal growth factor inhibitor (-)-reveromycin B. J Org Chem 2001, 66, 7, 2382.

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)	41537	tert-butyl(dimethyl)[2-[(2R,3S)-3-methyl-6-methylenetetrahydro-2H-pyran-2-yl]ethoxy]silane; tert-butyl(dimethyl)silyl 2-[(2R,3S)-3-methyl-6-methylenetetrahydro-2H-pyran-2-yl]ethyl ether		C₁₅H₃₀O₂Si	详情	详情
(XVI)	14689	Methyl (triphenylphosphoranylidene)acetate; (methoxycarbonylmethylene)triphenylphosphorane；Methyl 2-(triphenyl-lambda(5)-phosphanylidene)acetate	2605-67-6	C₂₁H₁₉O₂P	详情	详情
(XXXIII)	45546	3-[[tert-butyl(dimethyl)silyl]oxy]propanal	570-24-1	C₉H₂₀O₂Si	详情	详情
(XXXIV)	50353	(E)-2-butenyl[bis[(1R,2R,5R)-2,6,6-trimethylbicyclo[3.1.1]hept-3-yl]]borane		C₂₄H₄₁B	详情	详情
(XXXV)	50354	(3R,4S)-1-[[tert-butyl(dimethyl)silyl]oxy]-4-methyl-5-hexen-3-ol		C₁₃H₂₈O₂Si	详情	详情
(XXXVI)	50355	(2R,3R)-5-[[tert-butyl(dimethyl)silyl]oxy]-3-hydroxy-2-methylpentanal		C₁₂H₂₆O₃Si	详情	详情
(XXXVII)	50356	methyl (E,4S,5R)-7-[[tert-butyl(dimethyl)silyl]oxy]-5-hydroxy-4-methyl-2-heptenoate		C₁₅H₃₀O₄Si	详情	详情
(XXXVIII)	50357	methyl (4S,5R)-7-[[tert-butyl(dimethyl)silyl]oxy]-5-hydroxy-4-methylheptanoate		C₁₅H₃₂O₄Si	详情	详情
(XXXIX)	50358	(5S,6R)-6-(2-[[tert-butyl(dimethyl)silyl]oxy]ethyl)-5-methyltetrahydro-2H-pyran-2-one		C₁₄H₂₈O₃Si	详情	详情

Extended Information