methyl (3R)-4-[(2R,4S)-4-(acetyloxy)-3,4-dihydro-2H-pyran-2-yl]-3-methylbutanoate -Drug Synthesis Database

【结构式】

【分子编号】62939

【品名】methyl (3R)-4-[(2R,4S)-4-(acetyloxy)-3,4-dihydro-2H-pyran-2-yl]-3-methylbutanoate

【CA登记号】

【分子式】C₁₃H₂₀O₅

【分子量】256.2988

【元素组成】C 60.92% H 7.87% O 31.21%

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：(VI)

Synthesis of the acetylenic dihydropyran intermediate (VII): The reaction of the chiral oxazolinone (I) with allylmagnesium bromide (II) by means of CuBr, BF3/Et2O and Mg(OMe)2, followed by ozonolysis with O3 in dichloromethane gives the aldehyde (III), which is condensed with the enol ether (IV) by means of a chiral Cr catalist to yield the dihydropyranone(V). The reduction of (V) with NaBH4 and CeCl3, followed by acylation with Ac2O affords the acetoxydihydropyran derivative (VI). Which is finally condensed with the allenic tributyl tin compound (VII) and trimethylsilylmethyl magnesium chloride in THF to provide the target acetylenic dihydropyran intermediate (VIII).

参考文献中间体

合成目标

【1】 Williams, D.R.; et al.; Synthesis of (-)-laulimalide: An agent for microtubule stabilization. Tetrahedron Lett 2002, 43, 27, 4841.

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)	62935	(4R)-3-[(E)-2-butenoyl]-4-phenyl-1,3-oxazolidin-2-one		C₁₃H₁₃NO₃	详情	详情
(II)	10386	Allyl(bromo)magnesium	1730-25-2	C₃H₅BrMg	详情	详情
(III)	62936	Methyl (3R)-3-methyl-5-oxopentanoate		C₇H₁₂O₃	详情	详情
(IV)	62937	{[(E)-3-methoxy-1-methylene-2-propenyl]oxy}(trimethyl)silane; (E)-3-methoxy-1-methylene-2-propenyl trimethylsilyl ether		C₈H₁₆O₂Si	详情	详情
(V)	62938	methyl (3R)-3-methyl-4-[(2R)-4-oxo-3,4-dihydro-2H-pyran-2-yl]butanoate		C₁₁H₁₆O₄	详情	详情
(VI)	62939	methyl (3R)-4-[(2R,4S)-4-(acetyloxy)-3,4-dihydro-2H-pyran-2-yl]-3-methylbutanoate		C₁₃H₂₀O₅	详情	详情
(VII)	62940	2-[1,1'-biphenyl]-4-ylethyl 2-(tributylstannyl)-2,3-butadienyl ether; 4-(2-{[2-(tributylstannyl)-2,3-butadienyl]oxy}ethyl)-1,1'-biphenyl		C₃₀H₄₄OSn	详情	详情
(VIII)	62941	2-[1,1'-biphenyl]-4-ylethyl 4-((2R,6R)-6-{(2S)-2-methyl-4-[(trimethylsilyl)methyl]-4-pentenyl}-5,6-dihydro-2H-pyran-2-yl)-2-butynyl ether; 4-(2-{[4-((2R,6R)-6-{(2S)-2-methyl-4-[(trimethylsilyl)methyl]-4-pentenyl}-5,6-dihydro-2H-pyran-2-yl)-2-butynyl]oxy}ethyl)-1,1'-biphenyl		C₃₃H₄₄O₂Si	详情	详情

Extended Information