(1S,3R,7S,8S,8aR)-8-{2-[(7R,9R)-9-hydroxy-1,4,6-trioxaspiro[4.5]dec-7-yl]ethyl}-3,7-dimethyl-1,2,3,7,8,8a-hexahydro-1-naphthalenyl 2,2-dimethylbutanoate -Drug Synthesis Database

【结构式】

【分子编号】64418

【品名】(1S,3R,7S,8S,8aR)-8-{2-[(7R,9R)-9-hydroxy-1,4,6-trioxaspiro[4.5]dec-7-yl]ethyl}-3,7-dimethyl-1,2,3,7,8,8a-hexahydro-1-naphthalenyl 2,2-dimethylbutanoate

【CA登记号】

【分子式】C₂₇H₄₂O₆

【分子量】462.62688

【元素组成】C 70.1% H 9.15% O 20.75%

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)

The reaction of lovastatin (I) with benzoyl chloride (II) and pyridine gives the expected benzoate (III), which is treated with ethyleneglycol (IV), triethyl orthoformate and H2SO4 to yield the cyclic orthoformate (V). The methylation of (V) by means of MeI and BuLi in pyrrolidine affords the 2,2-dimethylbutyrate ester (VI), which is finally deprotected with HCl in THF to provide the target simvastatin.

参考文献中间体

合成目标

【1】 Dabak, K.; Adiyaman, M.; A new method for the synthesis of antihypercholesterolemic agent simvastatin. Helv Chim Acta 2003, 86, 3, 673.

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)	64415	(1S,3R,7S,8S,8aR)-8-{2-[(2R,4R)-4-hydroxy-6-oxotetrahydro-2H-pyran-2-yl]ethyl}-3,7-dimethyl-1,2,3,7,8,8a-hexahydro-1-naphthalenyl (2S)-2-methylbutanoate		C₂₄H₃₆O₅	详情	详情
(II)	10463	Benzoyl chloride	98-88-4	C₇H₅ClO	详情	详情
(III)	64416	(2R,4R)-2-[2-((1S,2S,6R,8S,8aR)-2,6-dimethyl-8-{[(2S)-2-methylbutanoyl]oxy}-1,2,6,7,8,8a-hexahydro-1-naphthalenyl)ethyl]-6-oxotetrahydro-2H-pyran-4-yl benzoate		C₃₁H₄₀O₆	详情	详情
(IV)	11295	Polyethylene glycol;1,2-Ethanediol;Monoethylene glycol; Ethylene glycol	107-21-1	C₂H₆O₂	详情	详情
(V)	64417	(7R,9R)-7-[2-((1S,2S,6R,8S,8aR)-2,6-dimethyl-8-{[(2S)-2-methylbutanoyl]oxy}-1,2,6,7,8,8a-hexahydro-1-naphthalenyl)ethyl]-1,4,6-trioxaspiro[4.5]dec-9-yl benzoate		C₃₃H₄₄O₇	详情	详情
(VI)	64418	(1S,3R,7S,8S,8aR)-8-{2-[(7R,9R)-9-hydroxy-1,4,6-trioxaspiro[4.5]dec-7-yl]ethyl}-3,7-dimethyl-1,2,3,7,8,8a-hexahydro-1-naphthalenyl 2,2-dimethylbutanoate		C₂₇H₄₂O₆	详情	详情

Extended Information