4-Methyl-2-pentenal -Drug Synthesis Database

【结构式】

【分子编号】57111

【品名】4-Methyl-2-pentenal

【CA登记号】5362-56-1

【分子式】C₆H₁₀O

【分子量】98.1448

【元素组成】C 73.43% H 10.27% O 16.3%

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：(II)

The condensation of the chiral imide (I) with aldehyde (II) by means of Et2B-OTf and DIEA in dichloromethane gives the hydroxy-imide (III), which is protected with Tbdms-Cl and imidazole to yield the silyl ether (IV). The cleavage of the chiral auxiliary of (IV), followed by reduction with DIBAL in THF affords the aldehyde (V), which is condensed with the silylated enol ether (VI) by means of SnCl4 in dichloromethane to provide the target intermediate, the phenyl thioester (VII).

参考文献中间体

合成目标

【1】 Boeckman, R.K.; Clark, T.J.; Shook, B.C.; A practical enantioselective total synthesis of the bengamides B, E, and Z. Org Lett 2002, 4, 12, 2109.
【2】 Boeckman, R.K.; et al.; The development of a convergent and efficient enantioselective synthesis of the bengamides via a common polyol intermediate. Helv Chim Acta 2002, 85, 12, 4532.

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)	57110	4,5,5-trimethyl-2-[2-(2-naphthyloxy)acetyl]-2-azabicyclo[2.2.1]heptan-3-one		C₂₁H₂₃NO₃	详情	详情
(II)	57111	4-Methyl-2-pentenal	5362-56-1	C₆H₁₀O	详情	详情
(III)	57112	2-[(2S,3R,4E)-3-hydroxy-6-methyl-2-(2-naphthyloxy)-4-heptenoyl]-4,5,5-trimethyl-2-azabicyclo[2.2.1]heptan-3-one		C₂₇H₃₃NO₄	详情	详情
(IV)	57113	2-[(2S,3R,4E)-3-{[tert-butyl(dimethyl)silyl]oxy}-6-methyl-2-(2-naphthyloxy)-4-heptenoyl]-4,5,5-trimethyl-2-azabicyclo[2.2.1]heptan-3-one		C₃₃H₄₇NO₄Si	详情	详情
(V)	57114	(2S,3R,4E)-3-{[tert-butyl(dimethyl)silyl]oxy}-6-methyl-2-(2-naphthyloxy)-4-heptenal		C₂₄H₃₄O₃Si	详情	详情
(VI)	57115	(Z)-2-methoxy-1-(phenylsulfanyl)ethenyl trimethylsilyl ether; {[(Z)-2-methoxy-1-(phenylsulfanyl)ethenyl]oxy}(trimethyl)silane		C₁₂H₁₈O₂SSi	详情	详情
(VII)	57116	S-phenyl (2R,3S,4R,5R,6E)-5-{[tert-butyl(dimethyl)silyl]oxy}-3-hydroxy-2-methoxy-8-methyl-4-(2-naphthyloxy)-6-nonenethioate		C₃₃H₄₄O₅SSi	详情	详情

Extended Information