(E)-(2S,4R,5R,8R)-9-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-4,6,8-trimethyl-non-6-en-3-one

Base Information

Chemical Name:(E)-(2S,4R,5R,8R)-9-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-4,6,8-trimethyl-non-6-en-3-one
CAS No.:905732-34-5
Molecular Formula:C₂₅H₄₂O₄Si
Molecular Weight:434.692
Hs Code.:

Synonyms:(E)-(2S,4R,5R,8R)-9-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-4,6,8-trimethyl-non-6-en-3-one

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Chemical Property of (E)-(2S,4R,5R,8R)-9-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-4,6,8-trimethyl-non-6-en-3-one

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Technology Process of (E)-(2S,4R,5R,8R)-9-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-4,6,8-trimethyl-non-6-en-3-one

There total 6 articles about (E)-(2S,4R,5R,8R)-9-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-4,6,8-trimethyl-non-6-en-3-one 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: 85.0%

: 373645-82-0
(E)-(R)-5-Benzyloxy-2,4-dimethyl-pent-2-enal

: 187590-50-7
(S) 4-(tert-butyldimethylsilyloxy)-3-pentanone

: 905732-34-5
(E)-(2S,4R,5R,8R)-9-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-4,6,8-trimethyl-non-6-en-3-one

Guidance literature:: With N-ethyl-N,N-diisopropylamine; titanium tetrachloride; In dichloromethane; at -78 ℃; for 3h;
DOI:10.1016/j.tetlet.2006.05.010

Reference yield:

: 81927-55-1
O-benzyl 2,2,2-trichloroacetimidate

: 905732-34-5
(E)-(2S,4R,5R,8R)-9-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-4,6,8-trimethyl-non-6-en-3-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: TfOH / cyclohexane; CH₂Cl₂ / 5 h / 0 °C

1.2: 85 percent / LAH / diethyl ether / 0.08 h / 0 °C

2.1: (COCl)2; Et₃N; DMSO / CH₂Cl₂ / -78 °C

3.1: CH₂Cl₂ / 3 h / 20 °C

4.1: LAH / diethyl ether / 0.17 h / 0 °C

5.1: SO₃-Py; Et₃N / dimethylsulfoxide; CH₂Cl₂ / 0.5 h / 0 °C

6.1: 85 percent / i-Pr₂NEt / TiCl₄ / CH₂Cl₂ / 3 h / -78 °C

With lithium aluminium tetrahydride; oxalyl dichloride; pyridine-SO₃ complex; trifluorormethanesulfonic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; titanium tetrachloride; In diethyl ether; dichloromethane; cyclohexane; dimethyl sulfoxide;
DOI:10.1016/j.tetlet.2006.05.010

Reference yield:

: 143680-11-9
(E)-5-Benzyloxy-2,3-dimethyl-2-pentensaeureethylester

: 905732-34-5
(E)-(2S,4R,5R,8R)-9-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-4,6,8-trimethyl-non-6-en-3-one

Guidance literature:: Multi-step reaction with 3 steps

1: LAH / diethyl ether / 0.17 h / 0 °C

2: SO₃-Py; Et₃N / dimethylsulfoxide; CH₂Cl₂ / 0.5 h / 0 °C

3: 85 percent / i-Pr₂NEt / TiCl₄ / CH₂Cl₂ / 3 h / -78 °C

With lithium aluminium tetrahydride; pyridine-SO₃ complex; triethylamine; N-ethyl-N,N-diisopropylamine; titanium tetrachloride; In diethyl ether; dichloromethane; dimethyl sulfoxide;
DOI:10.1016/j.tetlet.2006.05.010