(E)-(3R,4S,5R,7S)-7-Benzyloxy-10-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-4,8-dimethyl-dec-8-en-1-yn-5-ol

Base Information

• Chemical Name: (E)-(3R,4S,5R,7S)-7-Benzyloxy-10-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-4,8-dimethyl-dec-8-en-1-yn-5-ol
• CAS No.: 169898-05-9
• Molecular Formula: C₂₆H₄₂O₄Si
• Molecular Weight: 446.703

Synonyms:(E)-(3R,4S,5R,7S)-7-Benzyloxy-10-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-4,8-dimethyl-dec-8-en-1-yn-5-ol

Chemical Property of (E)-(3R,4S,5R,7S)-7-Benzyloxy-10-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-4,8-dimethyl-dec-8-en-1-yn-5-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of (E)-(3R,4S,5R,7S)-7-Benzyloxy-10-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-4,8-dimethyl-dec-8-en-1-yn-5-ol

There total 13 articles about (E)-(3R,4S,5R,7S)-7-Benzyloxy-10-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-4,8-dimethyl-dec-8-en-1-yn-5-ol 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: 83.0%

(E)-(3R,4S,5R,7S)-7-Benzyloxy-10-(tert-butyl-dimethyl-silanyloxy)-4,8-dimethyl-dec-8-en-1-yne-3,5-diol (169898-17-3) + methyl iodide (74-88-4) → (E)-(3R,4S,5R,7S)-7-Benzyloxy-10-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-4,8-dimethyl-dec-8-en-1-yn-5-ol (169898-05-9)

Guidance literature:

With sodium hydride; In tetrahydrofuran; at -78 - 20 ℃;

DOI:10.1021/jo034011x

Reference yield:

tert-butyldimethylsiloxyacetaldehyde (102191-92-4) → (E)-(3R,4S,5R,7S)-7-Benzyloxy-10-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-4,8-dimethyl-dec-8-en-1-yn-5-ol (169898-05-9)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 84 percent / benzene / 48 h / 0 - 20 °C

2.1: diisopropylamine; n-BuLi / tetrahydrofuran / 1 h / -78 °C

2.2: 78 percent / tetrahydrofuran / 0.08 h

3.1: (-)-diisopropyl tartrate; Ti(O-iPr)4; tert-butylhydroperoxide / molecular sieves 3 Angstroem / CH₂Cl₂ / 20 h / -20 °C

3.2: 40 percent / FeSO₄; citric acid / H₂O; CH₂Cl₂

4.1: 76 percent / TfOH

5.1: DIBAL-H

6.1: dibutylboron triflate; diisopropylethylamine / CH₂Cl₂ / 0.25 h / 0 °C

6.2: CH₂Cl₂ / 3 h / -78 °C

6.3: 89 percent / sodium acetate; hydrogen peroxide / methanol; CH₂Cl₂; H₂O / 1.5 h / 0 °C

7.1: 95 percent / trimethylaluminum / hexane; tetrahydrofuran / 0 - 20 °C

8.1: 66 percent / tetrahydrofuran / 15 h / 20 °C

9.1: 84 percent / diethylmethoxyborane; sodium borohydride / tetrahydrofuran / 3.5 h / -78 °C

10.1: 83 percent / sodium hydride / tetrahydrofuran; various solvent(s) / -78 - 20 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium tetrahydroborate; n-butyllithium; (-)-diisopropyl tartrate; trifluorormethanesulfonic acid; di-n-butylboryl trifluoromethanesulfonate; diethyl methoxy borane; trimethylaluminum; sodium hydride; diisobutylaluminium hydride; diisopropylamine; N-ethyl-N,N-diisopropylamine; 3 A molecular sieve; In tetrahydrofuran; hexane; dichloromethane; benzene; 1.1: Wittig olefination;

DOI:10.1021/jo034011x

Reference yield:

(Z)-1,4-bis(tert-butyldimethylsilanyloxy)but-2-ene (132835-15-5) → (E)-(3R,4S,5R,7S)-7-Benzyloxy-10-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-4,8-dimethyl-dec-8-en-1-yn-5-ol (169898-05-9)

Guidance literature:

Multi-step reaction with 11 steps

1.1: O₃ / CH₂Cl₂ / -78 °C

1.2: 100 percent / PPh₃ / CH₂Cl₂ / -78 - 20 °C

2.1: 84 percent / benzene / 48 h / 0 - 20 °C

3.1: diisopropylamine; n-BuLi / tetrahydrofuran / 1 h / -78 °C

3.2: 78 percent / tetrahydrofuran / 0.08 h

4.1: (-)-diisopropyl tartrate; Ti(O-iPr)4; tert-butylhydroperoxide / molecular sieves 3 Angstroem / CH₂Cl₂ / 20 h / -20 °C

4.2: 40 percent / FeSO₄; citric acid / H₂O; CH₂Cl₂

5.1: 76 percent / TfOH

6.1: DIBAL-H

7.1: dibutylboron triflate; diisopropylethylamine / CH₂Cl₂ / 0.25 h / 0 °C

7.2: CH₂Cl₂ / 3 h / -78 °C

7.3: 89 percent / sodium acetate; hydrogen peroxide / methanol; CH₂Cl₂; H₂O / 1.5 h / 0 °C

8.1: 95 percent / trimethylaluminum / hexane; tetrahydrofuran / 0 - 20 °C

9.1: 66 percent / tetrahydrofuran / 15 h / 20 °C

10.1: 84 percent / diethylmethoxyborane; sodium borohydride / tetrahydrofuran / 3.5 h / -78 °C

11.1: 83 percent / sodium hydride / tetrahydrofuran; various solvent(s) / -78 - 20 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium tetrahydroborate; n-butyllithium; (-)-diisopropyl tartrate; trifluorormethanesulfonic acid; di-n-butylboryl trifluoromethanesulfonate; diethyl methoxy borane; trimethylaluminum; sodium hydride; diisobutylaluminium hydride; ozone; diisopropylamine; N-ethyl-N,N-diisopropylamine; 3 A molecular sieve; In tetrahydrofuran; hexane; dichloromethane; benzene; 2.1: Wittig olefination;

DOI:10.1021/jo034011x

upstream raw materials:

(E)-(3R,4S,5R,7S)-7-Benzyloxy-10-(tert-butyl-dimethyl-silanyloxy)-4,8-dimethyl-dec-8-en-1-yne-3,5-diol

methyl iodide

tert-butyldimethylsiloxyacetaldehyde

benzyl bromide

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