diisopropyl {[1-({[methyl(dimethylene)-lambda~6~-sulfanyl]oxy}methyl)cyclopropyl]oxy}methylphosphonate -Drug Synthesis Database

【结构式】

【分子编号】63954

【品名】diisopropyl {[1-({[methyl(dimethylene)-lambda~6~-sulfanyl]oxy}methyl)cyclopropyl]oxy}methylphosphonate

【CA登记号】

【分子式】C₁₄H₂₉O₅PS

【分子量】340.421022

【元素组成】C 49.4% H 8.59% O 23.5% P 9.1% S 9.42%

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：(VI)

The key intermediate, cyclopropanol (I), was prepared by titanium-mediated Kulinkovich cyclopropanation in over 80% yield as a white solid. Etherification of compound (I) with diisopropyl bromomethylphosphonate, followed by sequential desilylation, mesylation and coupling reaction with 6-chloroguanine (VII), gave compound (VIII). Finally, hydrolysis of compound (VIII) in the presence of TMSBr afforded LB-80317.

参考文献中间体

合成目标

【1】 Hwang, J.-T.; Choi, J.-R.; Novel phosphonate nucleosides as antiviral agents. Drugs Fut 2004, 29, 2, 163.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	60566	ethyl 2-{[tert-butyl(diphenyl)silyl]oxy}acetate	C₂₀H₂₆O₃Si	详情	详情
(II)	60567	1-({[tert-butyl(diphenyl)silyl]oxy}methyl)cyclopropanol	C₂₀H₂₆O₂Si	详情	详情
(III)	60568	diisopropyl bromomethylphosphonate	C₇H₁₆BrO₃P	详情	详情
(IV)	60569	diisopropyl {[1-({[tert-butyl(diphenyl)silyl]oxy}methyl)cyclopropyl]oxy}methylphosphonate	C₂₇H₄₁O₅PSi	详情	详情
(V)	60570	diisopropyl {[1-(hydroxymethyl)cyclopropyl]oxy}methylphosphonate	C₁₁H₂₃O₅P	详情	详情
(VI)	63954	diisopropyl {[1-({[methyl(dimethylene)-lambda~6~-sulfanyl]oxy}methyl)cyclopropyl]oxy}methylphosphonate	C₁₄H₂₉O₅PS	详情	详情
(VII)	63955	6,9-dichloro-9H-purin-2-ylamine; 6,9-dichloro-9H-purin-2-amine	C₅H₃Cl₂N₅	详情	详情
(VIII)	63956	diisopropyl ({1-[(2-amino-6-chloro-9H-purin-9-yl)methyl]cyclopropyl}oxy)methylphosphonate	C₁₆H₂₅ClN₅O₄P	详情	详情

合成路线2

该中间体在本合成路线中的序号：(VI)

The key intermediate, cyclopropanol (I), was prepared by titanium-mediated Kulinkovich cyclopropanation in over 80% yield as a white solid. Etherification of compound (I) with diisopropyl bromomethylphosphonate, followed by sequential desilylation, mesylation and coupling reaction with 6-chloroguanine (VII), gave compound (VIII). Finally, hydrogenation of compound (VIII) in the presence of TMSBr afforded LB-80331.

参考文献中间体

合成目标

【1】 Hwang, J.-T.; Choi, J.-R.; Novel phosphonate nucleosides as antiviral agents. Drugs Fut 2004, 29, 2, 163.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	60566	ethyl 2-{[tert-butyl(diphenyl)silyl]oxy}acetate	C₂₀H₂₆O₃Si	详情	详情
(II)	60567	1-({[tert-butyl(diphenyl)silyl]oxy}methyl)cyclopropanol	C₂₀H₂₆O₂Si	详情	详情
(III)	60568	diisopropyl bromomethylphosphonate	C₇H₁₆BrO₃P	详情	详情
(IV)	60569	diisopropyl {[1-({[tert-butyl(diphenyl)silyl]oxy}methyl)cyclopropyl]oxy}methylphosphonate	C₂₇H₄₁O₅PSi	详情	详情
(V)	60570	diisopropyl {[1-(hydroxymethyl)cyclopropyl]oxy}methylphosphonate	C₁₁H₂₃O₅P	详情	详情
(VI)	63954	diisopropyl {[1-({[methyl(dimethylene)-lambda~6~-sulfanyl]oxy}methyl)cyclopropyl]oxy}methylphosphonate	C₁₄H₂₉O₅PS	详情	详情
(VII)	63955	6,9-dichloro-9H-purin-2-ylamine; 6,9-dichloro-9H-purin-2-amine	C₅H₃Cl₂N₅	详情	详情
(VIII)	63956	diisopropyl ({1-[(2-amino-6-chloro-9H-purin-9-yl)methyl]cyclopropyl}oxy)methylphosphonate	C₁₆H₂₅ClN₅O₄P	详情	详情

Extended Information