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【结 构 式】

【分子编号】52396

【品名】　

【CA登记号】

【 分 子 式 】C59H89IO8Si2

【 分 子 量 】1109.42633

【元素组成】C 63.88% H 8.09% I 11.44% O 11.54% Si 5.06%
与该中间体有关的原料药合成路线共 4 条
合成路线1合成路线2合成路线3合成路线4

合成路线1

该中间体在本合成路线中的序号：(XXXIII)

Alcohol (XXIX) was converted to the corresponding tosylate (XXX) employing p-toluenesulfonyl chloride and pyridine. Replacement of the pivaloyl protecting group of (XXX) for a mono-methoxytrityl group, yielding (XXXII), was effected by reductive cleavage of the pivaloyl ester of (XXX) and then treatment of alcohol (XXXI) with methoxytrityl chloride. Displacement of the tosylate group of (XXXII) by NaI in refluxing acetone provided the alkyl iodide (XXXIII).

参考文献 中间体
合成目标
【1】 Littlefield, B.A.; Zheng, W.; Seletsky, B.M.; Yu, M.J.; Palme, M.H.; Towle, M.J. (Eisai Co., Ltd.); Macrocyclic analogs and methods of their use and preparation. US 6214865; WO 9965894 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(XXIX) 52392 3-{5-[2-(6-{[5-(2,3-bis{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}propyl)-3-(hydroxymethyl)-4-(methyloxy)tetrahydro-2-furanyl]methyl}-4-methyl-5-methylidenetetrahydro-2H-pyran-2-yl)ethyl]-4-methylidenetetrahydro-2-furanyl}propyl 2,2-dimethylpropanoate C44H82O9Si2 详情 详情
(XXX) 52393 3-{(2S,5S)-5-[2-((2S,4R,6R)-6-{[(2S,3R,4R,5R)-5-((2S)-2,3-bis{[tert-butyl(dimethyl)silyl]oxy}propyl)-4-methoxy-3-({[(4-methylphenyl)sulfonyl]oxy}methyl)tetrahydro-2-furanyl]methyl}-4-methyl-5-methylenetetrahydro-2H-pyran-2-yl)ethyl]-4-methylenetetrahydro-2-furanyl}propyl 2,2-dimethylpropanoate C51H88O11SSi2 详情 详情
(XXXI) 52394 [5-(2,3-bis{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}propyl)-2-[(6-{2-[5-(3-hydroxypropyl)-3-methylidenetetrahydro-2-furanyl]ethyl}-4-methyl-3-methylidenetetrahydro-2H-pyran-2-yl)methyl]-4-(methyloxy)tetrahydro-3-furanyl]methyl 4-methylbenzenesulfonate C46H80O10SSi2 详情 详情
(XXXII) 52395 　 C66H96O11SSi2 详情 详情
(XXXIII) 52396 　 C59H89IO8Si2 详情 详情

合成路线2

该中间体在本合成路线中的序号：(XXXIII)

The aldehyde building block (XXXV) was obtained by DIBAL reduction of the previously described methyl ester (XXXIV). Lithiation of alkyl iodide (XXXIII) by means of tert-BuLi and then addition to aldehyde (XXXV) furnished the carbinol adduct (XXXVI). The methoxytrityl protecting group of (XXXVI) was then removed by acidic treatment, yielding (XXXVII). Oxidation of both free hydroxyl groups of (XXXVII) with Dess-Martin periodinane reagent gave rise to the keto aldehyde (XXXVIII).

参考文献 中间体
合成目标
【1】 Littlefield, B.A.; Zheng, W.; Seletsky, B.M.; Yu, M.J.; Palme, M.H.; Towle, M.J. (Eisai Co., Ltd.); Macrocyclic analogs and methods of their use and preparation. US 6214865; WO 9965894 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(XXXIII) 52396 　 C59H89IO8Si2 详情 详情
(XXXIV) 48420 methyl 2-[(2R,4aS,6S,7R,8S,8aS)-7,8-bis[[tert-butyl(dimethyl)silyl]oxy]-6-((1S,2E)-1-[[tert-butyl(dimethyl)silyl]oxy]-3-iodo-2-propenyl)octahydropyrano[3,2-b]pyran-2-yl]acetate C32H63IO7Si3 详情 详情
(XXXV) 52397 　 C31H61IO6Si3 详情 详情
(XXXVI) 52398 　 C90H151IO14Si5 详情 详情
(XXXVII) 52399 　 C70H135IO13Si5 详情 详情
(XXXVIII) 52400 　 C70H131IO13Si5 详情 详情

合成路线3

该中间体在本合成路线中的序号：(XXXIII)

Alcohol (XXIX) was converted to the corresponding tosylate (XXX) employing p-toluenesulfonyl chloride and pyridine. Replacement of the pivaloyl protecting group of (XXX) for a mono-methoxytrityl group, yielding (XXXII), was effected by reductive cleavage of the pivaloyl ester of (XXX) and then treatment of alcohol (XXXI) with methoxytrityl chloride. Displacement of the tosylate group of (XXXII) by NaI in refluxing acetone provided the alkyl iodide (XXXIII).

参考文献 中间体
合成目标
【1】 Littlefield, B.A.; Zheng, W.; Seletsky, B.M.; Yu, M.J.; Palme, M.H.; Towle, M.J. (Eisai Co., Ltd.); Macrocyclic analogs and methods of their use and preparation. US 6214865; WO 9965894 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(XXIX) 52392 3-{5-[2-(6-{[5-(2,3-bis{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}propyl)-3-(hydroxymethyl)-4-(methyloxy)tetrahydro-2-furanyl]methyl}-4-methyl-5-methylidenetetrahydro-2H-pyran-2-yl)ethyl]-4-methylidenetetrahydro-2-furanyl}propyl 2,2-dimethylpropanoate C44H82O9Si2 详情 详情
(XXX) 52393 3-{(2S,5S)-5-[2-((2S,4R,6R)-6-{[(2S,3R,4R,5R)-5-((2S)-2,3-bis{[tert-butyl(dimethyl)silyl]oxy}propyl)-4-methoxy-3-({[(4-methylphenyl)sulfonyl]oxy}methyl)tetrahydro-2-furanyl]methyl}-4-methyl-5-methylenetetrahydro-2H-pyran-2-yl)ethyl]-4-methylenetetrahydro-2-furanyl}propyl 2,2-dimethylpropanoate C51H88O11SSi2 详情 详情
(XXXI) 52394 [5-(2,3-bis{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}propyl)-2-[(6-{2-[5-(3-hydroxypropyl)-3-methylidenetetrahydro-2-furanyl]ethyl}-4-methyl-3-methylidenetetrahydro-2H-pyran-2-yl)methyl]-4-(methyloxy)tetrahydro-3-furanyl]methyl 4-methylbenzenesulfonate C46H80O10SSi2 详情 详情
(XXXII) 52395 　 C66H96O11SSi2 详情 详情
(XXXIII) 52396 　 C59H89IO8Si2 详情 详情

合成路线4

该中间体在本合成路线中的序号：(XXXIII)

The aldehyde building block (XXXV) was obtained by DIBAL reduction of the previously described methyl ester (XXXIV). Lithiation of alkyl iodide (XXXIII) by means of tert-BuLi and then addition to aldehyde (XXXV) furnished the carbinol adduct (XXXVI). The methoxytrityl protecting group of (XXXVI) was then removed by acidic treatment, yielding (XXXVII). Oxidation of both free hydroxyl groups of (XXXVII) with Dess-Martin periodinane reagent gave rise to the keto aldehyde (XXXVIII).

参考文献 中间体
合成目标
【1】 Littlefield, B.A.; Zheng, W.; Seletsky, B.M.; Yu, M.J.; Palme, M.H.; Towle, M.J. (Eisai Co., Ltd.); Macrocyclic analogs and methods of their use and preparation. US 6214865; WO 9965894 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(XXXIII) 52396 　 C59H89IO8Si2 详情 详情
(XXXIV) 48420 methyl 2-[(2R,4aS,6S,7R,8S,8aS)-7,8-bis[[tert-butyl(dimethyl)silyl]oxy]-6-((1S,2E)-1-[[tert-butyl(dimethyl)silyl]oxy]-3-iodo-2-propenyl)octahydropyrano[3,2-b]pyran-2-yl]acetate C32H63IO7Si3 详情 详情
(XXXV) 52397 　 C31H61IO6Si3 详情 详情
(XXXVI) 52398 　 C90H151IO14Si5 详情 详情
(XXXVII) 52399 　 C70H135IO13Si5 详情 详情
(XXXVIII) 52400 　 C70H131IO13Si5 详情 详情
Extended Information