Acetic acid (E)-(4S,5S,10R,11S,12S,13R,15R)-15-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-5,16-dimethoxy-10,12-dimethyl-9-oxo-13-triethylsilanyloxy-11-trimethylsilanyloxy-hexadec-7-enyl ester

Base Information

Chemical Name:Acetic acid (E)-(4S,5S,10R,11S,12S,13R,15R)-15-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-5,16-dimethoxy-10,12-dimethyl-9-oxo-13-triethylsilanyloxy-11-trimethylsilanyloxy-hexadec-7-enyl ester
CAS No.:869382-36-5
Molecular Formula:C₄₄H₈₂O₉Si₃
Molecular Weight:839.386
Hs Code.:

Acetic acid (E)-(4S,5S,10R,11S,12S,13R,15R)-15-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-5,16-dimethoxy-10,12-dimethyl-9-oxo-13-triethylsilanyloxy-11-trimethylsilanyloxy-hexadec-7-enyl ester

Synonyms:Acetic acid (E)-(4S,5S,10R,11S,12S,13R,15R)-15-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-5,16-dimethoxy-10,12-dimethyl-9-oxo-13-triethylsilanyloxy-11-trimethylsilanyloxy-hexadec-7-enyl ester

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Chemical Property of Acetic acid (E)-(4S,5S,10R,11S,12S,13R,15R)-15-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-5,16-dimethoxy-10,12-dimethyl-9-oxo-13-triethylsilanyloxy-11-trimethylsilanyloxy-hexadec-7-enyl ester

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Technology Process of Acetic acid (E)-(4S,5S,10R,11S,12S,13R,15R)-15-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-5,16-dimethoxy-10,12-dimethyl-9-oxo-13-triethylsilanyloxy-11-trimethylsilanyloxy-hexadec-7-enyl ester

There total 18 articles about Acetic acid (E)-(4S,5S,10R,11S,12S,13R,15R)-15-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-5,16-dimethoxy-10,12-dimethyl-9-oxo-13-triethylsilanyloxy-11-trimethylsilanyloxy-hexadec-7-enyl ester 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: 88.0%

: 869382-28-5
Acetic acid (4S,5S)-4-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-7-oxo-heptyl ester

: 869382-29-6
((3R,4S,5S,6R,8R)-8-Benzyloxy-9-methoxy-3,5-dimethyl-2-oxo-6-triethylsilanyloxy-4-trimethylsilanyloxy-nonyl)-phosphonic acid dimethyl ester

: 869382-36-5
Acetic acid (E)-(4S,5S,10R,11S,12S,13R,15R)-15-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-5,16-dimethoxy-10,12-dimethyl-9-oxo-13-triethylsilanyloxy-11-trimethylsilanyloxy-hexadec-7-enyl ester

Guidance literature:: With barium dihydroxide; In tetrahydrofuran;
DOI:10.1021/ja0549289

Reference yield:

: 869382-33-2
(S)-2-Methoxy-5-methyl-hex-4-enal

: 869382-36-5
Acetic acid (E)-(4S,5S,10R,11S,12S,13R,15R)-15-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-5,16-dimethoxy-10,12-dimethyl-9-oxo-13-triethylsilanyloxy-11-trimethylsilanyloxy-hexadec-7-enyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: 79 percent / TiCl₄ / CH₂Cl₂ / 0.5 h / -78 °C

2.1: 97 percent / 2,6-lutidine / CH₂Cl₂ / -78 °C

3.1: catecholborane; RhCl(PPh₃)3 / tetrahydrofuran

3.2: aq. H₂O₂; NaOH / tetrahydrofuran

4.1: Et₃N; DMAP / CH₂Cl₂

5.1: O₃ / CH₂Cl₂ / -78 °C

5.2: Me₂S / CH₂Cl₂

6.1: 88 percent / aq. Ba(OH)2 / tetrahydrofuran

With 2,6-dimethylpyridine; dmap; barium dihydroxide; RhCl(PPh₃)3; titanium tetrachloride; ozone; triethylamine; benzo[1,3,2]dioxaborole; In tetrahydrofuran; dichloromethane; 6.1: Horner-Wadsworth-Emmons reaction;
DOI:10.1021/ja0549289

Reference yield:

: (S)-2-Methoxy-5-methyl-hex-4-en-1-ol

: 869382-36-5
Acetic acid (E)-(4S,5S,10R,11S,12S,13R,15R)-15-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-5,16-dimethoxy-10,12-dimethyl-9-oxo-13-triethylsilanyloxy-11-trimethylsilanyloxy-hexadec-7-enyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: 99 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 25 °C

2.1: 79 percent / TiCl₄ / CH₂Cl₂ / 0.5 h / -78 °C

3.1: 97 percent / 2,6-lutidine / CH₂Cl₂ / -78 °C

4.1: catecholborane; RhCl(PPh₃)3 / tetrahydrofuran

4.2: aq. H₂O₂; NaOH / tetrahydrofuran

5.1: Et₃N; DMAP / CH₂Cl₂

6.1: O₃ / CH₂Cl₂ / -78 °C

6.2: Me₂S / CH₂Cl₂

7.1: 88 percent / aq. Ba(OH)2 / tetrahydrofuran

With 2,6-dimethylpyridine; dmap; barium dihydroxide; oxalyl dichloride; RhCl(PPh₃)3; titanium tetrachloride; ozone; dimethyl sulfoxide; triethylamine; benzo[1,3,2]dioxaborole; In tetrahydrofuran; dichloromethane; 1.1: Swern oxidation / 7.1: Horner-Wadsworth-Emmons reaction;
DOI:10.1021/ja0549289