(2R,3R,5R,6S,7S,8S)-2,6-Dibenzyloxy-3-(tert-butyldimethylsiloxy)-7-[1-(3-hydroxypropyl)vinyl]-5-(p-methoxybenzyloxy)-4,4,8-trimethylcyclooctanone

Base Information

Chemical Name:(2R,3R,5R,6S,7S,8S)-2,6-Dibenzyloxy-3-(tert-butyldimethylsiloxy)-7-[1-(3-hydroxypropyl)vinyl]-5-(p-methoxybenzyloxy)-4,4,8-trimethylcyclooctanone
CAS No.:222726-93-4
Molecular Formula:C₄₄H₆₂O₇Si
Molecular Weight:731.058
Hs Code.:

(2R,3R,5R,6S,7S,8S)-2,6-Dibenzyloxy-3-(tert-butyldimethylsiloxy)-7-[1-(3-hydroxypropyl)vinyl]-5-(p-methoxybenzyloxy)-4,4,8-trimethylcyclooctanone

Synonyms:(2R,3R,5R,6S,7S,8S)-2,6-Dibenzyloxy-3-(tert-butyldimethylsiloxy)-7-[1-(3-hydroxypropyl)vinyl]-5-(p-methoxybenzyloxy)-4,4,8-trimethylcyclooctanone

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Chemical Property of (2R,3R,5R,6S,7S,8S)-2,6-Dibenzyloxy-3-(tert-butyldimethylsiloxy)-7-[1-(3-hydroxypropyl)vinyl]-5-(p-methoxybenzyloxy)-4,4,8-trimethylcyclooctanone

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Technology Process of (2R,3R,5R,6S,7S,8S)-2,6-Dibenzyloxy-3-(tert-butyldimethylsiloxy)-7-[1-(3-hydroxypropyl)vinyl]-5-(p-methoxybenzyloxy)-4,4,8-trimethylcyclooctanone

There total 4 articles about (2R,3R,5R,6S,7S,8S)-2,6-Dibenzyloxy-3-(tert-butyldimethylsiloxy)-7-[1-(3-hydroxypropyl)vinyl]-5-(p-methoxybenzyloxy)-4,4,8-trimethylcyclooctanone 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: 97.0%

: 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

: 222726-93-4
(2R,3R,5R,6S,7S,8S)-2,6-Dibenzyloxy-3-(tert-butyldimethylsiloxy)-7-[1-(3-hydroxypropyl)vinyl]-5-(p-methoxybenzyloxy)-4,4,8-trimethylcyclooctanone

Guidance literature:: With hydrogenchloride; water; In tetrahydrofuran; at 0 ℃; for 0.833333h;
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

: 222726-93-4
(2R,3R,5R,6S,7S,8S)-2,6-Dibenzyloxy-3-(tert-butyldimethylsiloxy)-7-[1-(3-hydroxypropyl)vinyl]-5-(p-methoxybenzyloxy)-4,4,8-trimethylcyclooctanone

Guidance literature:: Multi-step reaction with 3 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

3.1: 97 percent / HCl; H₂O / tetrahydrofuran / 0.83 h / 0 °C

With 1H-imidazole; hydrogenchloride; water; tert.-butyl lithium; In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide; pentane; 1.1: Etherification / 2.1: Metallation / 2.2: Substitution / 2.3: Addition / 3.1: Hydrolysis;
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

: 222726-93-4
(2R,3R,5R,6S,7S,8S)-2,6-Dibenzyloxy-3-(tert-butyldimethylsiloxy)-7-[1-(3-hydroxypropyl)vinyl]-5-(p-methoxybenzyloxy)-4,4,8-trimethylcyclooctanone

Guidance literature:: Multi-step reaction with 4 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

4.1: 97 percent / HCl; H₂O / tetrahydrofuran / 0.83 h / 0 °C

With 1H-imidazole; hydrogenchloride; lithium aluminium tetrahydride; water; 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 / 4.1: Hydrolysis;
DOI:10.1002/(sici)1521-3765(19990104)5:1<121::aid-chem121>3.3.co;2-f