Cyclopentanol, 3-[(1R,2E)-1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-(phenylmethoxy)-2- butenyl]-4-[(1E,6S)-6-(phenylmethoxy)-1-heptenyl]-, (1R,3R,4S)-

Base Information

Chemical Name:Cyclopentanol, 3-[(1R,2E)-1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-(phenylmethoxy)-2- butenyl]-4-[(1E,6S)-6-(phenylmethoxy)-1-heptenyl]-, (1R,3R,4S)-
CAS No.:664997-57-3
Molecular Formula:C36H54O4Si
Molecular Weight:578.908
Hs Code.:

Cyclopentanol,
3-[(1R,2E)-1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-(phenylmethoxy)-2-
butenyl]-4-[(1E,6S)-6-(phenylmethoxy)-1-heptenyl]-, (1R,3R,4S)-

Synonyms:

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of Cyclopentanol, 3-[(1R,2E)-1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-(phenylmethoxy)-2- butenyl]-4-[(1E,6S)-6-(phenylmethoxy)-1-heptenyl]-, (1R,3R,4S)-

Chemical Property:

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Technology Process of Cyclopentanol, 3-[(1R,2E)-1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-(phenylmethoxy)-2- butenyl]-4-[(1E,6S)-6-(phenylmethoxy)-1-heptenyl]-, (1R,3R,4S)-

There total 28 articles about Cyclopentanol, 3-[(1R,2E)-1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-(phenylmethoxy)-2- butenyl]-4-[(1E,6S)-6-(phenylmethoxy)-1-heptenyl]-, (1R,3R,4S)- which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

: 664997-52-8
(3R,4S)-3-[(E)-(R)-4-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-but-2-enyl]-4-((E)-(S)-6-benzyloxy-hept-1-enyl)-cyclopentanone

: 664997-57-3
(1R,3R,4S)-3-[(E)-(R)-4-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-but-2-enyl]-4-((E)-(S)-6-benzyloxy-hept-1-enyl)-cyclopentanol

Guidance literature:: With tert.-butyl lithium; diisobutylaluminium hydride; In tetrahydrofuran; toluene; pentane; at -78 ℃; for 0.5h; Inert atmosphere;
DOI:10.1021/ol800137f

Reference yield: 75.0%

: 664997-52-8
(3R,4S)-3-[(E)-(R)-4-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-but-2-enyl]-4-((E)-(S)-6-benzyloxy-hept-1-enyl)-cyclopentanone

: 664997-57-3
(1R,3R,4S)-3-[(E)-(R)-4-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-but-2-enyl]-4-((E)-(S)-6-benzyloxy-hept-1-enyl)-cyclopentanol

: 664997-53-9
(1S,3R,4S)-3-[(E)-(R)-4-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-but-2-enyl]-4-((E)-(S)-6-benzyloxy-hept-1-enyl)-cyclopentanol

Guidance literature:: With samarium diiodide; In tetrahydrofuran; isopropyl alcohol; at 0 ℃; for 3h; diastereoselective reaction; Inert atmosphere;
DOI:10.1021/ol800137f

Reference yield:

: 29264-40-2
5-pentenylbenzoate

: 664997-57-3
(1R,3R,4S)-3-[(E)-(R)-4-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-but-2-enyl]-4-((E)-(S)-6-benzyloxy-hept-1-enyl)-cyclopentanol

Guidance literature:: Multi-step reaction with 11 steps

1.1: 95.1 percent / mCPBA

2.1: 46.4 percent / (R,R)-salenCo(III)OAc / H₂O / 72 h / 10 - 20 °C

3.1: 99 percent / H₂ / Pd/C; Co(OAc)4 / methanol / 20 °C / 760 Torr

4.1: TMSOTf / CH₂Cl₂; petroleum ether / 2 h

5.1: 2.70 g / NaOMe / methanol / 3 h / 20 °C

6.1: 73.3 percent / DMAP; Et₃N / CH₂Cl₂ / 20 °C

7.1: 86.1 percent / dimethylsulfoxide / 20 °C

8.1: 72.4 percent / cateholborane / 36 h / 20 °C

9.1: 95.4 percent / I₂; aq. NaOH / diethyl ether / 0.33 h / 20 °C

10.1: BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

10.2: MeCuCNLi / tetrahydrofuran; hexane; diethyl ether / 1 h / -78 °C

10.3: 92.6 percent / tetrahydrofuran; hexane; diethyl ether / 1 h / -78 °C

11.1: 87 mg / (S)-2-methyl-CBS-oxazaborolidine; BH₃*Me₂S / tetrahydrofuran; toluene / 0.25 h / 0 °C

With dmap; sodium hydroxide; n-butyllithium; (S,S)-(salen)cobalt(III)(OAc); trimethylsilyl trifluoromethanesulfonate; dimethylsulfide borane complex; hydrogen; iodine; sodium methylate; triethylamine; 3-chloro-benzenecarboperoxoic acid; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; benzo[1,3,2]dioxaborole; palladium on activated charcoal; Co(OAc)4; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; dimethyl sulfoxide; toluene; Petroleum ether; 2.1: Jacobsen kinetic hydrolytic resolution / 10.3: Michael addition;