4-{[(chlorocarbonyl)oxy]methyl}-2,2-dimethyl-1,3-dioxolane -Drug Synthesis Database

【结构式】

【分子编号】56226

【品名】4-{[(chlorocarbonyl)oxy]methyl}-2,2-dimethyl-1,3-dioxolane

【CA登记号】

【分子式】C₇H₁₁ClO₄

【分子量】194.61464

【元素组成】C 43.2% H 5.7% Cl 18.22% O 32.88%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(II)

Acylation of paclitaxel (I) with 2,3-O-isopropylideneglyceryl chloroformate (II) produced the 2',7-bis-carbonate (III). Subsequent acid hydrolysis of the acetonide groups of (III) furnished the corresponding bis-(dihydroxypropyl)carbonate (IV). The 2'-ester of (IV) was then selectively hydrolyzed using a phosphate buffer at pH 6.5.

参考文献中间体

合成目标

【1】 Seligson, A.L.; et al.; A new prodrug of paclitaxel: Synthesis of Protaxel. Anti-Cancer Drugs 2001, 12, 4, 305.
【2】 Sovak, M.; Douglass, J.G.; Bressi, J.C.; Seligson, A. (Biophysica Foundation); Novel taxoids. JP 1998509461; US 5801191; WO 9638138 .

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)	10595	(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetoxy)-15-[[(2R,3S)-3-(benzoylamino)-2-hydroxy-3-phenylpropanoyl]oxy]-1,9-dihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate	33069-62-4	C₄₇H₅₁NO₁₄	详情	详情
(II)	56226	4-{[(chlorocarbonyl)oxy]methyl}-2,2-dimethyl-1,3-dioxolane		C₇H₁₁ClO₄	详情	详情
(III)	56227	(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetyloxy)-15-{[(2R,3S)-3-(benzoylamino)-2-({[(2,2-dimethyl-1,3-dioxolan-4-yl)methoxy]carbonyl}oxy)-3-phenylpropanoyl]oxy}-9-({[(2,2-dimethyl-1,3-dioxolan-4-yl)methoxy]carbonyl}oxy)-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0~3,10~.0~4,7~]heptadec-13-en-2-yl benzoate		C₆₁H₇₁NO₂₂	详情	详情
(IV)	56228	(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetyloxy)-15-[((2R,3S)-3-(benzoylamino)-2-{[(2,3-dihydroxypropoxy)carbonyl]oxy}-3-phenylpropanoyl)oxy]-9-{[(2,3-dihydroxypropoxy)carbonyl]oxy}-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0~3,10~.0~4,7~]heptadec-13-en-2-yl benzoate		C₅₅H₆₃NO₂₂	详情	详情

合成路线2

该中间体在本合成路线中的序号：(II)

Condensation of etoposide (I) with 2,2-dimethyl-1,3-dioxolan-4-ylmethyl chloroformate (II) provides the carbonate ester (III). Then, acidic hydrolysis of the acetonide group of (III) leads to the target compound.

参考文献中间体

合成目标

【1】 Wrasidlo, W.; et al.; Synthesis, hydrolytic activation and cytotoxicity of etoposide prodrugs. Bioorg Med Chem Lett 2002, 12, 4, 557.

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)	13041	Etoposide; (5R,5aR,8aR,9S)-9-[[(2R,4aR,6R,7R,8R,8aS)-7,8-Dihydroxy-2-methylhexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-5-(4-hydroxy-3,5-dimethoxyphenyl)-5,8,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one	33419-42-0	C₂₉H₃₂O₁₃	详情	详情
(II)	56226	4-{[(chlorocarbonyl)oxy]methyl}-2,2-dimethyl-1,3-dioxolane		C₇H₁₁ClO₄	详情	详情
(III)	62776	4-((5R,5aR,8aR,9S)-9-{[(2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-methylhexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy}-6-oxo-5,5a,6,8,8a,9-hexahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl)-2,6-dimethoxyphenyl (2,2-dimethyl-1,3-dioxolan-4-yl)methyl car		C₃₆H₄₂O₁₇	详情	详情

Extended Information