(1S,2R,5S,6R,8R,9R,11R)-11-(2-Benzenesulfonyl-ethyl)-5-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-6,10,10-trimethyl-12-oxo-13-oxa-tricyclo[6.4.1.0^1,6]tridecane-9-carbonitrile

Base Information

• Chemical Name: (1S,2R,5S,6R,8R,9R,11R)-11-(2-Benzenesulfonyl-ethyl)-5-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-6,10,10-trimethyl-12-oxo-13-oxa-tricyclo[6.4.1.0^1,6]tridecane-9-carbonitrile
• CAS No.: 166533-83-1
• Molecular Formula: C₃₇H₆₁NO₆SSi₂
• Molecular Weight: 704.131

Synonyms:

Chemical Property of (1S,2R,5S,6R,8R,9R,11R)-11-(2-Benzenesulfonyl-ethyl)-5-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-6,10,10-trimethyl-12-oxo-13-oxa-tricyclo[6.4.1.0^1,6]tridecane-9-carbonitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of (1S,2R,5S,6R,8R,9R,11R)-11-(2-Benzenesulfonyl-ethyl)-5-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-6,10,10-trimethyl-12-oxo-13-oxa-tricyclo[6.4.1.0^1,6]tridecane-9-carbonitrile

There total 2 articles about (1S,2R,5S,6R,8R,9R,11R)-11-(2-Benzenesulfonyl-ethyl)-5-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-6,10,10-trimethyl-12-oxo-13-oxa-tricyclo[6.4.1.0^1,6]tridecane-9-carbonitrile 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:

(benzenesulfonyl)methyllithium (116511-95-6) + (1S,2R,5S,6R,8R,9R)-5-(tert-Butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-6,10,10-trimethyl-11-methylene-12-oxo-13-oxa-tricyclo[6.4.1.01,6]tridecane-9-carbonitrile → (1S,2R,5S,6R,8R,9R,11R)-11-(2-Benzenesulfonyl-ethyl)-5-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-6,10,10-trimethyl-12-oxo-13-oxa-tricyclo[6.4.1.01,6]tridecane-9-carbonitrile (166533-83-1)

Guidance literature:

In tetrahydrofuran; at -78 ℃;

DOI:10.1016/00404-0399(50)1084U-

Reference yield:

methylphenylsulfonate (3112-85-4) + (1S,2R,5S,6R,8R)-5-(tert-Butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-6,10,10-trimethyl-11-methylene-12-oxo-13-oxa-tricyclo[6.4.1.01,6]tridecane-9-carbonitrile → (1S,2R,5S,6R,8R,9R,11R)-11-(2-Benzenesulfonyl-ethyl)-5-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-6,10,10-trimethyl-12-oxo-13-oxa-tricyclo[6.4.1.01,6]tridecane-9-carbonitrile (166533-83-1) + (1S,2R,5S,6R,8R,9S,11R)-11-(2-Benzenesulfonyl-ethyl)-5-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-6,10,10-trimethyl-12-oxo-13-oxa-tricyclo[6.4.1.01,6]tridecane-9-carbonitrile

Guidance literature:

With n-butyllithium; Yield given. Yields of byproduct given; 1.) THF, hexane, 0 deg C, 45 min, 2.) THF, hexane, -78 deg C, 1 h;

DOI:10.1016/S0040-4020(98)00056-8

Reference yield:

(1S,2R,5S,6R,8R,9R,11R)-11-(2-Benzenesulfonyl-ethyl)-5-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-6,10,10-trimethyl-12-oxo-13-oxa-tricyclo[6.4.1.01,6]tridecane-9-carbonitrile (166533-83-1) → C31H47NO5SSi

Guidance literature:

With sodium cyanoborohydride; In trifluoroacetic acid; at 0 ℃;

DOI:10.1016/00404-0399(50)1084U-

upstream raw materials:

(benzenesulfonyl)methyllithium

methylphenylsulfonate

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