(2R,3R,5R,6S,7S,8S)-2,6-Dibenzyloxy-3-(tert-butyldimethylsiloxy)-5-(p-methoxybenzyloxy)-4,4,8-trimethyl-7-{1-[3-(triethylsiloxy)propyl]vinyl}cyclooctanone

Base Information

Chemical Name:(2R,3R,5R,6S,7S,8S)-2,6-Dibenzyloxy-3-(tert-butyldimethylsiloxy)-5-(p-methoxybenzyloxy)-4,4,8-trimethyl-7-{1-[3-(triethylsiloxy)propyl]vinyl}cyclooctanone
CAS No.:194420-15-0
Molecular Formula:C₅₀H₇₆O₇Si₂
Molecular Weight:845.32
Hs Code.:

(2R,3R,5R,6S,7S,8S)-2,6-Dibenzyloxy-3-(tert-butyldimethylsiloxy)-5-(p-methoxybenzyloxy)-4,4,8-trimethyl-7-{1-[3-(triethylsiloxy)propyl]vinyl}cyclooctanone

Synonyms:(2R,3R,5R,6S,7S,8S)-2,6-Dibenzyloxy-3-(tert-butyldimethylsiloxy)-5-(p-methoxybenzyloxy)-4,4,8-trimethyl-7-{1-[3-(triethylsiloxy)propyl]vinyl}cyclooctanone

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Chemical Property of (2R,3R,5R,6S,7S,8S)-2,6-Dibenzyloxy-3-(tert-butyldimethylsiloxy)-5-(p-methoxybenzyloxy)-4,4,8-trimethyl-7-{1-[3-(triethylsiloxy)propyl]vinyl}cyclooctanone

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Technology Process of (2R,3R,5R,6S,7S,8S)-2,6-Dibenzyloxy-3-(tert-butyldimethylsiloxy)-5-(p-methoxybenzyloxy)-4,4,8-trimethyl-7-{1-[3-(triethylsiloxy)propyl]vinyl}cyclooctanone

There total 3 articles about (2R,3R,5R,6S,7S,8S)-2,6-Dibenzyloxy-3-(tert-butyldimethylsiloxy)-5-(p-methoxybenzyloxy)-4,4,8-trimethyl-7-{1-[3-(triethylsiloxy)propyl]vinyl}cyclooctanone 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: 92.0%

: 178626-24-9
2-bromo-5-(triethylsilyloxy)pentene

: (4S,5R,7R,8R)-4,8-Dibenzyloxy-7-(tert-butyldimethylsiloxy)-5-(p-methoxybenzyloxy)-2,6,6-trimethyl-2-cycloocten-1-one

: 194420-15-0
(2R,3R,5R,6S,7S,8S)-2,6-Dibenzyloxy-3-(tert-butyldimethylsiloxy)-5-(p-methoxybenzyloxy)-4,4,8-trimethyl-7-{1-[3-(triethylsiloxy)propyl]vinyl}cyclooctanone

Guidance literature:: 2-bromo-5-(triethylsilyloxy)pentene; With tert.-butyl lithium; In diethyl ether; pentane; at -78 ℃; for 0.333333h;

In diethyl ether; pentane; at 0 ℃; for 0.5h;

(4S,5R,7R,8R)-4,8-Dibenzyloxy-7-(tert-butyldimethylsiloxy)-5-(p-methoxybenzyloxy)-2,6,6-trimethyl-2-cycloocten-1-one; In diethyl ether; pentane; at -23 ℃; for 1.33333h;
DOI:10.1002/(sici)1521-3765(19990104)5:1<121::aid-chem121>3.3.co;2-f

Reference yield:

: 64180-78-5
4-bromopent-4-en-1-ol

: 194420-15-0
(2R,3R,5R,6S,7S,8S)-2,6-Dibenzyloxy-3-(tert-butyldimethylsiloxy)-5-(p-methoxybenzyloxy)-4,4,8-trimethyl-7-{1-[3-(triethylsiloxy)propyl]vinyl}cyclooctanone

Guidance literature:: Multi-step reaction with 2 steps

1.1: 94 percent / imidazole / dimethylformamide / 1.5 h / 0 °C

2.1: t-BuLi / diethyl ether; pentane / 0.33 h / -78 °C

2.2: CuCN / diethyl ether; pentane / 0.5 h / 0 °C

2.3: 92 percent / diethyl ether; pentane / 1.33 h / -23 °C

With 1H-imidazole; tert.-butyl lithium; In diethyl ether; N,N-dimethyl-formamide; pentane; 1.1: Etherification / 2.1: Metallation / 2.2: Substitution / 2.3: Addition;
DOI:10.1002/(sici)1521-3765(19990104)5:1<121::aid-chem121>3.3.co;2-f

Reference yield:

: 35804-44-5
ethyl 4-bromo-4-pentenoate

: 194420-15-0
(2R,3R,5R,6S,7S,8S)-2,6-Dibenzyloxy-3-(tert-butyldimethylsiloxy)-5-(p-methoxybenzyloxy)-4,4,8-trimethyl-7-{1-[3-(triethylsiloxy)propyl]vinyl}cyclooctanone

Guidance literature:: Multi-step reaction with 3 steps

1.1: LiAlH₄ / tetrahydrofuran / 0.67 h / 0 °C

2.1: 94 percent / imidazole / dimethylformamide / 1.5 h / 0 °C

3.1: t-BuLi / diethyl ether; pentane / 0.33 h / -78 °C

3.2: CuCN / diethyl ether; pentane / 0.5 h / 0 °C

3.3: 92 percent / diethyl ether; pentane / 1.33 h / -23 °C

With 1H-imidazole; lithium aluminium tetrahydride; tert.-butyl lithium; In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide; pentane; 1.1: Reduction / 2.1: Etherification / 3.1: Metallation / 3.2: Substitution / 3.3: Addition;
DOI:10.1002/(sici)1521-3765(19990104)5:1<121::aid-chem121>3.3.co;2-f