(3R,4R,6R,7S,8R,12R)-3,7-Dibenzyloxy-4-(tert-butyldimethylsiloxy)-12-hydroxy-6-(p-methoxybenzyloxy)-5,5-dimethyl-9-methylenebicyclo[6.4.0]dodecan-2-one

Base Information

Chemical Name:(3R,4R,6R,7S,8R,12R)-3,7-Dibenzyloxy-4-(tert-butyldimethylsiloxy)-12-hydroxy-6-(p-methoxybenzyloxy)-5,5-dimethyl-9-methylenebicyclo[6.4.0]dodecan-2-one
CAS No.:222726-92-3
Molecular Formula:C₄₃H₅₈O₇Si
Molecular Weight:715.015
Hs Code.:

(3R,4R,6R,7S,8R,12R)-3,7-Dibenzyloxy-4-(tert-butyldimethylsiloxy)-12-hydroxy-6-(p-methoxybenzyloxy)-5,5-dimethyl-9-methylenebicyclo[6.4.0]dodecan-2-one

Synonyms:(3R,4R,6R,7S,8R,12R)-3,7-Dibenzyloxy-4-(tert-butyldimethylsiloxy)-12-hydroxy-6-(p-methoxybenzyloxy)-5,5-dimethyl-9-methylenebicyclo[6.4.0]dodecan-2-one

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Chemical Property of (3R,4R,6R,7S,8R,12R)-3,7-Dibenzyloxy-4-(tert-butyldimethylsiloxy)-12-hydroxy-6-(p-methoxybenzyloxy)-5,5-dimethyl-9-methylenebicyclo[6.4.0]dodecan-2-one

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Technology Process of (3R,4R,6R,7S,8R,12R)-3,7-Dibenzyloxy-4-(tert-butyldimethylsiloxy)-12-hydroxy-6-(p-methoxybenzyloxy)-5,5-dimethyl-9-methylenebicyclo[6.4.0]dodecan-2-one

There total 3 articles about (3R,4R,6R,7S,8R,12R)-3,7-Dibenzyloxy-4-(tert-butyldimethylsiloxy)-12-hydroxy-6-(p-methoxybenzyloxy)-5,5-dimethyl-9-methylenebicyclo[6.4.0]dodecan-2-one 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: 82.0%

: 178626-15-8
4-[(1S,2S,3R,5R,6R)-2,6-Dibenzyloxy-5-(tert-butyldimethylsiloxy)-3-(p-methoxybenzyloxy)-4,4-dimethyl-7-oxocyclooctyl]-4-pentenal

: (3R,4R,6R,7S,8R,12S)-3,7-Dibenzyloxy-4-(tert-butyldimethylsiloxy)-12-hydroxy-6-(p-methoxybenzyloxy)-5,5-dimethyl-9-methylenebicyclo[6.4.0]dodecan-2-one

: 222726-92-3
(3R,4R,6R,7S,8R,12R)-3,7-Dibenzyloxy-4-(tert-butyldimethylsiloxy)-12-hydroxy-6-(p-methoxybenzyloxy)-5,5-dimethyl-9-methylenebicyclo[6.4.0]dodecan-2-one

Guidance literature:: With sodium methylate; In methanol; at 20 ℃; for 6h;
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

: 222726-92-3
(3R,4R,6R,7S,8R,12R)-3,7-Dibenzyloxy-4-(tert-butyldimethylsiloxy)-12-hydroxy-6-(p-methoxybenzyloxy)-5,5-dimethyl-9-methylenebicyclo[6.4.0]dodecan-2-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: t-BuLi / diethyl ether; pentane / 0.5 h / -78 °C

1.2: lithium 2-thienylcyanocuprate / tetrahydrofuran; diethyl ether; pentane / 0.58 h / -78 °C

1.3: 91 percent / tetrahydrofuran; diethyl ether; pentane / 0.83 h / -45 - 0 °C

2.1: 89 percent / NMO; TPAP; molecular sieves 4 Angstroem / CH₂Cl₂ / 0.5 h / 0 °C

3.1: 18 percent / MeONa / methanol / 6 h / 20 °C

With N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; tert.-butyl lithium; sodium methylate; In methanol; diethyl ether; dichloromethane; pentane; 1.1: Metallation / 1.2: Substitution / 1.3: Addition / 2.1: Oxidation / 3.1: Cycloaddition;
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

: 222726-92-3
(3R,4R,6R,7S,8R,12R)-3,7-Dibenzyloxy-4-(tert-butyldimethylsiloxy)-12-hydroxy-6-(p-methoxybenzyloxy)-5,5-dimethyl-9-methylenebicyclo[6.4.0]dodecan-2-one

Guidance literature:: Multi-step reaction with 4 steps

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

2.1: t-BuLi / diethyl ether; pentane / 0.5 h / -78 °C

2.2: lithium 2-thienylcyanocuprate / tetrahydrofuran; diethyl ether; pentane / 0.58 h / -78 °C

2.3: 91 percent / tetrahydrofuran; diethyl ether; pentane / 0.83 h / -45 - 0 °C

3.1: 89 percent / NMO; TPAP; molecular sieves 4 Angstroem / CH₂Cl₂ / 0.5 h / 0 °C

4.1: 18 percent / MeONa / methanol / 6 h / 20 °C

With lithium aluminium tetrahydride; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; tert.-butyl lithium; sodium methylate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; pentane; 1.1: Reduction / 2.1: Metallation / 2.2: Substitution / 2.3: Addition / 3.1: Oxidation / 4.1: Cycloaddition;
DOI:10.1002/(sici)1521-3765(19990104)5:1<121::aid-chem121>3.3.co;2-f