Yaozh News Star Club Edu BBS TOP100 Customer Service APP
Iphone Download Android Download
  • English
  • 简体中文
Login Register
Search
Current Location： Home > Feedback Help Print

【结 构 式】

【分子编号】51430

【品名】(3S)-3-[[tert-butyl(dimethyl)silyl]oxy]-2,2-dimethyl-4-penten-1-ol

【CA登记号】

【 分 子 式 】C13H28O2Si

【 分 子 量 】244.44962

【元素组成】C 63.88% H 11.55% O 13.09% Si 11.49%
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：(IV)

The synthesis of the chiral 3-heptanone intermediate has been obtained as follows: The protection of the OH group of the chiral lactone (I) with Tbdms-Cl and imidazole gives the silyl ether (II), which is reduced with DIBAL to yield the lactol (III).The reaction of (III) with the Tebbe reagent affords the pentenol derivative (IV), which is oxidized with Dess-Martin periodinane (DMP), affording the aldehyde (V). The Grignard synthesis of (V) with ethylmagnesium bromide (VI) provides the 3-heptanol derivative (VII), which is hydroxylated at the terminal double bond by means of BH3/THF and H2O2, giving the diol (VIII). The selective protection of the primary OH group of (VIII) with Dmt-Cl, DIEA and DMAP yields the trityl ether (IX), which is finally oxidized with DMP to afford the desired chiral heptanone (X)

参考文献 中间体
合成目标
【1】 Martin, N.; Thomas, E.J.; Total syntheses of epothilones B and D: Applications of allylstannanes in organic synthesis. Tetrahedron Lett 2001, 42, 47, 8373.
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) 51427 D-Pantolactone; R(-)-2-Hydroxy-3,3-dimethyl-gamma-butyrolactone 599-04-2 C6H10O3 详情 详情
(II) 51428 (3R)-3-[[tert-butyl(dimethyl)silyl]oxy]-4,4-dimethyldihydro-2(3H)-furanone C12H24O3Si 详情 详情
(III) 51429 (3R)-3-[[tert-butyl(dimethyl)silyl]oxy]-4,4-dimethyltetrahydro-2-furanol C12H26O3Si 详情 详情
(IV) 51430 (3S)-3-[[tert-butyl(dimethyl)silyl]oxy]-2,2-dimethyl-4-penten-1-ol C13H28O2Si 详情 详情
(V) 51431 (3S)-3-[[tert-butyl(dimethyl)silyl]oxy]-2,2-dimethyl-4-pentenal C13H26O2Si 详情 详情
(VI) 24239 bromo(ethyl)magnesium；ethylmagnesium bromide 925-90-6 C2H5BrMg 详情 详情
(VII) 51432 (5S)-5-[[tert-butyl(dimethyl)silyl]oxy]-4,4-dimethyl-6-hepten-3-ol C15H32O2Si 详情 详情
(VIII) 51433 (3S)-3-[[tert-butyl(dimethyl)silyl]oxy]-4,4-dimethyl-1,5-heptanediol C15H34O3Si 详情 详情
(IX) 51434 (5S)-7-[bis(4-methoxyphenyl)(phenyl)methoxy]-5-[[tert-butyl(dimethyl)silyl]oxy]-4,4-dimethyl-3-heptanol C36H52O5Si 详情 详情
(X) 51435 (5S)-7-[bis(4-methoxyphenyl)(phenyl)methoxy]-5-[[tert-butyl(dimethyl)silyl]oxy]-4,4-dimethyl-3-heptanone C36H50O5Si 详情 详情

合成路线2

该中间体在本合成路线中的序号：(IV)

The synthesis of the chiral 3-heptanone intermediate has been obtained as follows: The protection of the OH group of the chiral lactone (I) with Tbdms-Cl and imidazole gives the silyl ether (II), which is reduced with DIBAL to yield the lactol (III).The reaction of (III) with the Tebbe reagent affords the pentenol derivative (IV), which is oxidized with Dess-Martin periodinane (DMP), affording the aldehyde (V). The Grignard synthesis of (V) with ethylmagnesium bromide (VI) provides the 3-heptanol derivative (VII), which is hydroxylated at the terminal double bond by means of BH3/THF and H2O2, giving the diol (VIII). The selective protection of the primary OH group of (VIII) with Dmt-Cl, DIEA and DMAP yields the trityl ether (IX), which is finally oxidized with DMP to afford the desired chiral heptanone (X).

参考文献 中间体
合成目标
【1】 Martin, N.; Thomas, E.J.; Total syntheses of epothilones B and D: Applications of allylstannanes in organic synthesis. Tetrahedron Lett 2001, 42, 47, 8373.
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) 51427 D-Pantolactone; R(-)-2-Hydroxy-3,3-dimethyl-gamma-butyrolactone 599-04-2 C6H10O3 详情 详情
(II) 51428 (3R)-3-[[tert-butyl(dimethyl)silyl]oxy]-4,4-dimethyldihydro-2(3H)-furanone C12H24O3Si 详情 详情
(III) 51429 (3R)-3-[[tert-butyl(dimethyl)silyl]oxy]-4,4-dimethyltetrahydro-2-furanol C12H26O3Si 详情 详情
(IV) 51430 (3S)-3-[[tert-butyl(dimethyl)silyl]oxy]-2,2-dimethyl-4-penten-1-ol C13H28O2Si 详情 详情
(V) 51431 (3S)-3-[[tert-butyl(dimethyl)silyl]oxy]-2,2-dimethyl-4-pentenal C13H26O2Si 详情 详情
(VI) 24239 bromo(ethyl)magnesium；ethylmagnesium bromide 925-90-6 C2H5BrMg 详情 详情
(VII) 51432 (5S)-5-[[tert-butyl(dimethyl)silyl]oxy]-4,4-dimethyl-6-hepten-3-ol C15H32O2Si 详情 详情
(VIII) 51433 (3S)-3-[[tert-butyl(dimethyl)silyl]oxy]-4,4-dimethyl-1,5-heptanediol C15H34O3Si 详情 详情
(IX) 51434 (5S)-7-[bis(4-methoxyphenyl)(phenyl)methoxy]-5-[[tert-butyl(dimethyl)silyl]oxy]-4,4-dimethyl-3-heptanol C36H52O5Si 详情 详情
(X) 51435 (5S)-7-[bis(4-methoxyphenyl)(phenyl)methoxy]-5-[[tert-butyl(dimethyl)silyl]oxy]-4,4-dimethyl-3-heptanone C36H50O5Si 详情 详情
Extended Information