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

Base Information

Chemical Name:(E)-(3R,4S,5R,7S)-7-Benzyloxy-10-(tert-butyl-dimethyl-silanyloxy)-4,8-dimethyl-dec-8-en-1-yne-3,5-diol
CAS No.:169898-17-3
Molecular Formula:C₂₅H₄₀O₄Si
Molecular Weight:432.676
Hs Code.:

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

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

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

There total 12 articles about (E)-(3R,4S,5R,7S)-7-Benzyloxy-10-(tert-butyl-dimethyl-silanyloxy)-4,8-dimethyl-dec-8-en-1-yne-3,5-diol 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: 84.0%

: 169898-16-2
(E)-(4S,5R,7S)-7-Benzyloxy-10-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-4,8-dimethyl-dec-8-en-1-yn-3-one

: 169898-17-3
(E)-(3R,4S,5R,7S)-7-Benzyloxy-10-(tert-butyl-dimethyl-silanyloxy)-4,8-dimethyl-dec-8-en-1-yne-3,5-diol

Guidance literature:: With sodium tetrahydroborate; diethyl methoxy borane;
DOI:10.1016/0040-4039(95)01194-M

Reference yield:

: 102191-92-4
tert-butyldimethylsiloxyacetaldehyde

: 169898-17-3
(E)-(3R,4S,5R,7S)-7-Benzyloxy-10-(tert-butyl-dimethyl-silanyloxy)-4,8-dimethyl-dec-8-en-1-yne-3,5-diol

Guidance literature:: Multi-step reaction with 9 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

With titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium tetrahydroborate; n-butyllithium; (-)-diisopropyl tartrate; trifluorormethanesulfonic acid; di-n-butylboryl trifluoromethanesulfonate; diethyl methoxy borane; trimethylaluminum; 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:

: 132835-15-5
(Z)-1,4-bis(tert-butyldimethylsilanyloxy)but-2-ene

: 169898-17-3
(E)-(3R,4S,5R,7S)-7-Benzyloxy-10-(tert-butyl-dimethyl-silanyloxy)-4,8-dimethyl-dec-8-en-1-yne-3,5-diol

Guidance literature:: Multi-step reaction with 10 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

With titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium tetrahydroborate; n-butyllithium; (-)-diisopropyl tartrate; trifluorormethanesulfonic acid; di-n-butylboryl trifluoromethanesulfonate; diethyl methoxy borane; trimethylaluminum; 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