(2E,6R,8S,10R,12E)-10-((tert-butyldimethylsilyl)oxy)-6-hydroxy-3,12-dimethyl-1-phenylhexadeca-2,12,15-trien-8-yl propionate

Base Information

Chemical Name:(2E,6R,8S,10R,12E)-10-((tert-butyldimethylsilyl)oxy)-6-hydroxy-3,12-dimethyl-1-phenylhexadeca-2,12,15-trien-8-yl propionate
CAS No.:1376331-05-3
Molecular Formula:C₃₃H₅₄O₄Si
Molecular Weight:542.875
Hs Code.:

Synonyms:(2E,6R,8S,10R,12E)-10-((tert-butyldimethylsilyl)oxy)-6-hydroxy-3,12-dimethyl-1-phenylhexadeca-2,12,15-trien-8-yl propionate

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Chemical Property of (2E,6R,8S,10R,12E)-10-((tert-butyldimethylsilyl)oxy)-6-hydroxy-3,12-dimethyl-1-phenylhexadeca-2,12,15-trien-8-yl propionate

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Technology Process of (2E,6R,8S,10R,12E)-10-((tert-butyldimethylsilyl)oxy)-6-hydroxy-3,12-dimethyl-1-phenylhexadeca-2,12,15-trien-8-yl propionate

There total 15 articles about (2E,6R,8S,10R,12E)-10-((tert-butyldimethylsilyl)oxy)-6-hydroxy-3,12-dimethyl-1-phenylhexadeca-2,12,15-trien-8-yl propionate 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: 93.0%

: 1376331-04-2
(2E,8R,10R,12E)-10-((tert-butyldimethylsilyl)oxy)-8-hydroxy-3,12-dimethyl-1-phenylhexadeca-2,12,15-trien-6-one

: 123-38-6
propionaldehyde

: 1376331-05-3
(2E,6R,8S,10R,12E)-10-((tert-butyldimethylsilyl)oxy)-6-hydroxy-3,12-dimethyl-1-phenylhexadeca-2,12,15-trien-8-yl propionate

Guidance literature:: With samarium diiodide; In tetrahydrofuran; at -20 ℃; for 1h; Inert atmosphere;
DOI:10.1002/anie.201200871

Reference yield: 93.0%

: C₃₀H₄₈O₃Si

: 123-38-6
propionaldehyde

: 1376331-05-3
(2E,6R,8S,10R,12E)-10-((tert-butyldimethylsilyl)oxy)-6-hydroxy-3,12-dimethyl-1-phenylhexadeca-2,12,15-trien-8-yl propionate

Guidance literature:: With samarium diiodide; stereoselective reaction;
DOI:10.2533/chimia.2013.227

Reference yield:

: 1375950-76-7
(E)-5-methyl-7-phenylhept-5-en-2-one

: 1376331-05-3
(2E,6R,8S,10R,12E)-10-((tert-butyldimethylsilyl)oxy)-6-hydroxy-3,12-dimethyl-1-phenylhexadeca-2,12,15-trien-8-yl propionate

Guidance literature:: Multi-step reaction with 2 steps

1.1: triethylamine; B-chlorodiisopinocampheylborane / dichloromethane / 3 h / -78 °C / Inert atmosphere

1.2: 16 h / -78 - -20 °C / Inert atmosphere

1.3: 1.5 h / 0 °C / pH 7 / aq. phosphate buffer

2.1: samarium diiodide / tetrahydrofuran / 1 h / -20 °C / Inert atmosphere

With samarium diiodide; triethylamine; B-chlorodiisopinocampheylborane; In tetrahydrofuran; dichloromethane; 1.1: Paterson aldol reaction / 1.2: Paterson aldol reaction / 2.1: Evans-Tishchenko reduction;
DOI:10.1002/anie.201200871