4-ethyl 3-methyl (3S,4R,5R)-3-(1,3-benzodioxol-5-ylcarbonyl)-2-oxo-5-(3,4,5-trimethoxyphenyl)tetrahydro-3,4-furandicarboxylate -Drug Synthesis Database

【结构式】

【分子编号】35006

【品名】4-ethyl 3-methyl (3S,4R,5R)-3-(1,3-benzodioxol-5-ylcarbonyl)-2-oxo-5-(3,4,5-trimethoxyphenyl)tetrahydro-3,4-furandicarboxylate

【CA登记号】

【分子式】C₂₆H₂₆O₁₂

【分子量】530.48524

【元素组成】C 58.87% H 4.94% O 36.19%

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：(LV)

The cyclization of 3,4,5-trimethoxycinnamic acid ethyl ester (LI) with malonic acid ethyl ester potassium salt (LII) by means of Mn(OAc)3 gives the tetrahydrofuranone (LIII), which is acylated with 1,3-benzodioxol-5-ylcarbonyl chloride (LIV) yielding the tetrahydrofuranone (LV). Finally, this compound is rearranged and decarboxylated with SnCl4 to the target intermediate (XI).

参考文献中间体

合成目标

【1】 Ward, R.S.; Synthesis of podophyllotoxin and related compounds. Synthesis 1992, 719.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(XI)	34966	ethyl (5R,6R)-8-oxo-5-(3,4,5-trimethoxyphenyl)-5,6,7,8-tetrahydronaphtho[2,3-d][1,3]dioxole-6-carboxylate		C₂₃H₂₄O₈	详情	详情
(LI)	35003	ethyl (E)-3-(3,4,5-trimethoxyphenyl)-2-propenoate		C₁₄H₁₈O₅	详情	详情
(LII)	35004	potassium 3-methoxy-3-oxopropanoate	38330-80-2	C₄H₅KO₄	详情	详情
(LIII)	35005	4-ethyl 3-methyl (3S,4R,5R)-2-oxo-5-(3,4,5-trimethoxyphenyl)tetrahydro-3,4-furandicarboxylate		C₁₈H₂₂O₉	详情	详情
(LIV)	28821	1,3-benzodioxole-5-carbonyl chloride	20850-43-5	C₈H₅ClO₃	详情	详情
(LV)	35006	4-ethyl 3-methyl (3S,4R,5R)-3-(1,3-benzodioxol-5-ylcarbonyl)-2-oxo-5-(3,4,5-trimethoxyphenyl)tetrahydro-3,4-furandicarboxylate		C₂₆H₂₆O₁₂	详情	详情

Extended Information