(5S,6S,9R,11R,E)-11-(tert-butyldimethylsilyloxy)-2,2,3,3,6,9,18,18-octamethyl-17,17-diphenyl-5-vinyl-4,16-dioxa-3,17-disilanonadec-7-ene

Base Information

• Chemical Name: (5S,6S,9R,11R,E)-11-(tert-butyldimethylsilyloxy)-2,2,3,3,6,9,18,18-octamethyl-17,17-diphenyl-5-vinyl-4,16-dioxa-3,17-disilanonadec-7-ene
• CAS No.: 1207434-22-7
• Molecular Formula: C₄₃H₇₄O₃Si₃
• Molecular Weight: 723.315
• Mol file: 1207434-22-7.mol

Synonyms:(5S,6S,9R,11R,E)-11-(tert-butyldimethylsilyloxy)-2,2,3,3,6,9,18,18-octamethyl-17,17-diphenyl-5-vinyl-4,16-dioxa-3,17-disilanonadec-7-ene

Chemical Property of (5S,6S,9R,11R,E)-11-(tert-butyldimethylsilyloxy)-2,2,3,3,6,9,18,18-octamethyl-17,17-diphenyl-5-vinyl-4,16-dioxa-3,17-disilanonadec-7-ene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5S,6S,9R,11R,E)-11-(tert-butyldimethylsilyloxy)-2,2,3,3,6,9,18,18-octamethyl-17,17-diphenyl-5-vinyl-4,16-dioxa-3,17-disilanonadec-7-ene

There total 26 articles about (5S,6S,9R,11R,E)-11-(tert-butyldimethylsilyloxy)-2,2,3,3,6,9,18,18-octamethyl-17,17-diphenyl-5-vinyl-4,16-dioxa-3,17-disilanonadec-7-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: 96.0%

(5S,6S,7R,11R,Z)-11-(tert-butyldimethylsilyloxy)-2,2,3,3,6,18,18-heptamethyl-17,17-diphenyl-5-vinyl-4,16-dioxa-3,17-disilanonadec-8-en-7-ol (1207434-21-6) + lithium dimethylcuprate (15681-48-8) → (5S,6S,9R,11R,E)-11-(tert-butyldimethylsilyloxy)-2,2,3,3,6,9,18,18-octamethyl-17,17-diphenyl-5-vinyl-4,16-dioxa-3,17-disilanonadec-7-ene (1207434-22-7)

Guidance literature:

(5S,6S,7R,11R,Z)-11-(tert-butyldimethylsilyloxy)-2,2,3,3,6,18,18-heptamethyl-17,17-diphenyl-5-vinyl-4,16-dioxa-3,17-disilanonadec-8-en-7-ol; With potassium hexamethylsilazane; diethyl chlorophosphate; In diethyl ether; cyclohexane; at -78 - 0 ℃; for 1h; Inert atmosphere;

lithium dimethylcuprate; In diethyl ether; hexane; at -10 - 20 ℃; optical yield given as %de; Inert atmosphere;

DOI:10.1021/jo301066p

Reference yield:

C46H81O7PSi3 + methyllithium (917-54-4) → (5S,6S,9R,11R,E)-11-(tert-butyldimethylsilyloxy)-2,2,3,3,6,9,18,18-octamethyl-17,17-diphenyl-5-vinyl-4,16-dioxa-3,17-disilanonadec-7-ene (1207434-22-7)

Guidance literature:

methyllithium; With copper(l) iodide; In diethyl ether; at 0 ℃;

C₄₆H₈₁O₇PSi₃; In diethyl ether; toluene; at -40 - 20 ℃; optical yield given as %de; stereoselective reaction;

DOI:10.1021/ol902829e

Reference yield:

(R)-6-[(tert-butyldiphenylsilyl)oxy]-1,2-epoxyhexane (958635-16-0) → (5S,6S,9R,11R,E)-11-(tert-butyldimethylsilyloxy)-2,2,3,3,6,9,18,18-octamethyl-17,17-diphenyl-5-vinyl-4,16-dioxa-3,17-disilanonadec-7-ene (1207434-22-7)

Guidance literature:

Multi-step reaction with 8 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / -78 - 0 °C

1.2: 0.5 h / -78 °C

2.1: potassium carbonate / methanol / 16 h / 20 °C

3.1: 1H-imidazole / N,N-dimethyl-formamide / 3 h / 20 °C

4.1: n-butyllithium / tetrahydrofuran; hexane / -78 - 0 °C

4.2: -78 - 20 °C

5.1: sodium tetrahydroborate; cerium(III) chloride heptahydrate / ethanol / 5 h / -78 - -15 °C

5.2: 20 °C

6.1: quinoline; hydrogen / ethyl acetate / 1 h / 20 °C / 760.05 Torr / Inert atmosphere

7.1: potassium hexamethylsilazane / diethyl ether; toluene / 0.33 h / -78 °C

7.2: 1.67 h / -78 - -30 °C

8.1: copper(l) iodide / diethyl ether / 0 °C

8.2: -40 - 20 °C

With 1H-imidazole; quinoline; sodium tetrahydroborate; copper(l) iodide; n-butyllithium; cerium(III) chloride heptahydrate; hydrogen; potassium hexamethylsilazane; potassium carbonate; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; ethyl acetate; N,N-dimethyl-formamide; toluene; 5.1: Luche reduction;

DOI:10.1021/ol902829e

upstream raw materials:

methyllithium

(4R,2'R,3'S)-4-benzyl-3-[3-hydroxy-2-methylpent-4-enoyl]-oxazolidin-2-one

5-Hexen-1-ol

(R)-6-[(tert-butyldiphenylsilyl)oxy]-1,2-epoxyhexane