(2R,4S,5S)-5-(tert-butyldimethylsiloxy)-4-(tert-butyldiphenylsiloxy)-2-methylcycloheptanone

Base Information

• Chemical Name: (2R,4S,5S)-5-(tert-butyldimethylsiloxy)-4-(tert-butyldiphenylsiloxy)-2-methylcycloheptanone
• CAS No.: 1015071-66-5
• Molecular Formula: C₃₀H₄₆O₃Si₂
• Molecular Weight: 510.864

Synonyms:(2R,4S,5S)-5-(tert-butyldimethylsiloxy)-4-(tert-butyldiphenylsiloxy)-2-methylcycloheptanone

Chemical Property of (2R,4S,5S)-5-(tert-butyldimethylsiloxy)-4-(tert-butyldiphenylsiloxy)-2-methylcycloheptanone

Chemical Property:

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Technology Process of (2R,4S,5S)-5-(tert-butyldimethylsiloxy)-4-(tert-butyldiphenylsiloxy)-2-methylcycloheptanone

There total 2 articles about (2R,4S,5S)-5-(tert-butyldimethylsiloxy)-4-(tert-butyldiphenylsiloxy)-2-methylcycloheptanone 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:

(3R,5S,1'S)-5-[1-(tert-butyldimethylsiloxy)-3-iodopropyl]-3-methyldihydrofuran-2-one (1015071-64-3) + tert-butylchlorodiphenylsilane (58479-61-1) → (2R,4S,5S)-5-(tert-butyldimethylsiloxy)-4-(tert-butyldiphenylsiloxy)-2-methylcycloheptanone (1015071-66-5)

Guidance literature:

(3R,5S,1'S)-5-[1-(tert-butyldimethylsiloxy)-3-iodopropyl]-3-methyldihydrofuran-2-one; With tert.-butyl lithium; In tetrahydrofuran; pentane; at -78 ℃; for 0.5h; Inert atmosphere;

tert-butylchlorodiphenylsilane; With 1H-imidazole; dmap; In dichloromethane; at 20 ℃; for 48h; Inert atmosphere;

DOI:10.1021/ol8001333

Reference yield:

C14H28O3Si + tert-butylchlorodiphenylsilane (58479-61-1) → (2R,4S,5S)-5-(tert-butyldimethylsiloxy)-4-(tert-butyldiphenylsiloxy)-2-methylcycloheptanone (1015071-66-5)

Guidance literature:

With 1H-imidazole; dmap; In dichloromethane; at 20 ℃;

DOI:10.1016/j.tet.2010.08.061

Reference yield:

(2R,4S,5S)-5-(tert-butyldimethylsiloxy)-4-(tert-butyldiphenylsiloxy)-2-methylcycloheptanone (1015071-66-5) + vinyl magnesium bromide (1826-67-1) → (1R,2R,4S,5S)-5-(tert-butyldimethylsilyloxy)-4-(tert-butyldiphenylsilyloxy)-2-methyl-1-vinylcycloheptanol (1015071-68-7)

Guidance literature:

In tetrahydrofuran; for 6h; Inert atmosphere; Reflux;

DOI:10.1021/ol8001333

upstream raw materials:

(3R,5S,1'S)-5-[1-(tert-butyldimethylsiloxy)-3-iodopropyl]-3-methyldihydrofuran-2-one

tert-butylchlorodiphenylsilane

Downstream raw materials:

(1R,2R,4S,5S)-5-(tert-butyldimethylsilyloxy)-4-(tert-butyldiphenylsilyloxy)-2-methyl-1-vinylcycloheptanol

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