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

Base Information

Chemical Name:(E)-(4S,5R,7S)-7-Benzyloxy-10-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-4,8-dimethyl-dec-8-en-1-yn-3-one
CAS No.:169898-16-2
Molecular Formula:C₂₅H₃₈O₄Si
Molecular Weight:430.66
Hs Code.:

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

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

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

There total 10 articles about (E)-(4S,5R,7S)-7-Benzyloxy-10-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-4,8-dimethyl-dec-8-en-1-yn-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: 66.0%

: 169898-15-1
(E)-(2S,3R,5S)-5-Benzyloxy-8-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2,6-dimethyl-oct-6-enoic acid methoxy-methyl-amide

: 4301-14-8
acetylenemagnesium bromide

: 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

Guidance literature:: DOI:10.1016/0040-4039(95)01194-M

Reference yield:

: 102191-92-4
tert-butyldimethylsiloxyacetaldehyde

: 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

Guidance literature:: Multi-step reaction with 8 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

With titanium(IV) isopropylate; tert.-butylhydroperoxide; n-butyllithium; (-)-diisopropyl tartrate; trifluorormethanesulfonic acid; di-n-butylboryl trifluoromethanesulfonate; 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:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 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

Guidance literature:: Multi-step reaction with 10 steps

1.1: 100 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 0 - 20 °C

2.1: O₃ / CH₂Cl₂ / -78 °C

2.2: 100 percent / PPh₃ / CH₂Cl₂ / -78 - 20 °C

3.1: 84 percent / benzene / 48 h / 0 - 20 °C

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

4.2: 78 percent / tetrahydrofuran / 0.08 h

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

5.2: 40 percent / FeSO₄; citric acid / H₂O; CH₂Cl₂

6.1: 76 percent / TfOH

7.1: DIBAL-H

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

8.2: CH₂Cl₂ / 3 h / -78 °C

8.3: 89 percent / sodium acetate; hydrogen peroxide / methanol; CH₂Cl₂; H₂O / 1.5 h / 0 °C

9.1: 95 percent / trimethylaluminum / hexane; tetrahydrofuran / 0 - 20 °C

10.1: 66 percent / tetrahydrofuran / 15 h / 20 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; n-butyllithium; (-)-diisopropyl tartrate; trifluorormethanesulfonic acid; di-n-butylboryl trifluoromethanesulfonate; trimethylaluminum; diisobutylaluminium hydride; ozone; diisopropylamine; N-ethyl-N,N-diisopropylamine; 3 A molecular sieve; In tetrahydrofuran; hexane; dichloromethane; benzene; 3.1: Wittig olefination;
DOI:10.1021/jo034011x