(2Z,4R,5R,6R,7R)-6-benzoyloxy-4-methyl-1,5-di-(tert-butyldimethylsiloxy)-7,8-di-(triethylsiloxy)oct-2-ene

Base Information

Chemical Name:(2Z,4R,5R,6R,7R)-6-benzoyloxy-4-methyl-1,5-di-(tert-butyldimethylsiloxy)-7,8-di-(triethylsiloxy)oct-2-ene
CAS No.:251319-66-1
Molecular Formula:C₄₀H₇₈O₆Si₄
Molecular Weight:767.398
Hs Code.:

Synonyms:(2Z,4R,5R,6R,7R)-6-benzoyloxy-4-methyl-1,5-di-(tert-butyldimethylsiloxy)-7,8-di-(triethylsiloxy)oct-2-ene

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Chemical Property of (2Z,4R,5R,6R,7R)-6-benzoyloxy-4-methyl-1,5-di-(tert-butyldimethylsiloxy)-7,8-di-(triethylsiloxy)oct-2-ene

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Technology Process of (2Z,4R,5R,6R,7R)-6-benzoyloxy-4-methyl-1,5-di-(tert-butyldimethylsiloxy)-7,8-di-(triethylsiloxy)oct-2-ene

There total 13 articles about (2Z,4R,5R,6R,7R)-6-benzoyloxy-4-methyl-1,5-di-(tert-butyldimethylsiloxy)-7,8-di-(triethylsiloxy)oct-2-ene 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: 99.0%

: 994-30-9
triethylsilyl chloride

: 251319-59-2
(2R,3R,4R,5R,6Z)-3-benzoyloxy-5-methyl-4,8-di-(tert-butyldimethylsiloxy)-2,3-(oxirane) oct-6-en-1,2-diol

: 251319-66-1
(2Z,4R,5R,6R,7R)-6-benzoyloxy-4-methyl-1,5-di-(tert-butyldimethylsiloxy)-7,8-di-(triethylsiloxy)oct-2-ene

Guidance literature:: With triethylamine; In dichloromethane; at 20 ℃;
DOI:10.1016/S0040-4039(99)01481-1

Reference yield:

: 251319-56-9
(2R,3R,4E)-2-methyl-3-(tert-butyldimethylsilyloxy)-6-(phenylmethoxy)hex-4-en-1-al

: 251319-66-1
(2Z,4R,5R,6R,7R)-6-benzoyloxy-4-methyl-1,5-di-(tert-butyldimethylsiloxy)-7,8-di-(triethylsiloxy)oct-2-ene

Guidance literature:: Multi-step reaction with 7 steps

1: 89 percent / potassium hexamethyldisilazide; 18-crown-6 / tetrahydrofuran / 0.5 h / -78 °C

2: 100 percent / DIBAL / CH₂Cl₂ / 0.25 h / -78 °C

3: 97 percent / imidazole / dimethylformamide / 0.17 h

4: 97 percent / di-tert-butylbiphenyllithium / tetrahydrofuran / -78 °C

5: 82 percent / (-)-diethyltartrate; t-BuOOH; titanium(IV) isopropoxide / CH₂Cl₂ / 18 h / -28 °C

6: 80 percent / titanium(IV) isopropoxide / tetrahydrofuran / 18 h

7: 1.28 g / imidazole / dimethylformamide / 18 h

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; 18-crown-6 ether; potassium hexamethylsilazane; diisobutylaluminium hydride; lithium 4,4′-di-tert-butylbiphenylide; (-)-diethyl tartrate; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 1: Condensation / 2: Reduction / 3: Substitution / 4: Elimination / 5: Epoxidation / 6: Ring cleavage / 7: Substitution;
DOI:10.1016/S0040-4020(00)00804-8

Reference yield:

: 251319-57-0
(2E,4R,5R,6Z)-5-methyl-4,8-di-(tert-butyldimethylsiloxy)-octa-2,6-diene-1-ol

: 251319-66-1
(2Z,4R,5R,6R,7R)-6-benzoyloxy-4-methyl-1,5-di-(tert-butyldimethylsiloxy)-7,8-di-(triethylsiloxy)oct-2-ene

Guidance literature:: Multi-step reaction with 3 steps

1: 82 percent / (-)-diethyltartrate; t-BuOOH; titanium(IV) isopropoxide / CH₂Cl₂ / 18 h / -28 °C

2: 80 percent / titanium(IV) isopropoxide / tetrahydrofuran / 18 h

3: 1.28 g / imidazole / dimethylformamide / 18 h

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; (-)-diethyl tartrate; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 1: Epoxidation / 2: Ring cleavage / 3: Substitution;
DOI:10.1016/S0040-4020(00)00804-8