(1E)-1-methoxy-3-methyl-1,3-butadiene; methyl (1E)-3-methyl-1,3-butadienyl ether -Drug Synthesis Database

【结构式】

【分子编号】61171

【品名】(1E)-1-methoxy-3-methyl-1,3-butadiene; methyl (1E)-3-methyl-1,3-butadienyl ether

【CA登记号】

【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：(X)

The intermediate 4-methyl-3,6-dihydro-2H-pyran-2(S)-carbaldehyde (XIII) has been obtained as follows: The cyclization of 2-(Tbdms-O)acetaldehyde (IX) with 1-methoxy-3-methylbutadiene (X) by means of a chiral Cr catalyst gives the chiral dihydropyran derivative (XI), which is desilylated and demethoxylated by means of triethylsilane, BF3/Et2O and HCl to yield the dihydropyran methanol derivative (XII). Finally, this compound is oxidized to the target intermediate 4-methyl-3,6-dihydro-2H-pyran-2(S)-carbaldehyde (XIII) by means of oxalyl chloride , DMSO and TEA

参考文献中间体

合成目标

【1】 Paterson, I.; et al.; Total synthesis of the microtubule-stabilizing agent (-)-laulimalide. Org Lett 2001, 3, 20, 3149.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(IX)	61170	2-{[tert-butyl(dimethyl)silyl]oxy}acetaldehyde；tert-butyldimethylsilyloxy acetaldehyde	102191-92-4	C₈H₁₈O₂Si	详情	详情
(X)	61171	(1E)-1-methoxy-3-methyl-1,3-butadiene; methyl (1E)-3-methyl-1,3-butadienyl ether		C₆H₁₀O	详情	详情
(XI)	61172	tert-butyl(dimethyl)silyl [(2S,6R)-6-methoxy-4-methyl-3,6-dihydro-2H-pyran-2-yl]methyl ether; tert-butyl{[(2S,6R)-6-methoxy-4-methyl-3,6-dihydro-2H-pyran-2-yl]methoxy}dimethylsilane		C₁₄H₂₈O₃Si	详情	详情
(XII)	61173	[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]methanol		C₇H₁₂O₂	详情	详情
(XIII)	61148	(2S)-4-methyl-3,6-dihydro-2H-pyran-2-carbaldehyde		C₇H₁₀O₂	详情	详情

Extended Information