2α,10β-dibenzyloxy-11β-(t-butyldimethylsiloxy)-7β-hydroxy-1α-(p-methoxybenzyloxy)-8β,15,15-trimethyl-4-methylene-trans-bicyclo[6.4.0]dodecan-9-one

Base Information

• Chemical Name: 2α,10β-dibenzyloxy-11β-(t-butyldimethylsiloxy)-7β-hydroxy-1α-(p-methoxybenzyloxy)-8β,15,15-trimethyl-4-methylene-trans-bicyclo[6.4.0]dodecan-9-one
• CAS No.: 194420-17-2
• Molecular Formula: C₄₄H₆₀O₇Si
• Molecular Weight: 729.042
• Mol file: 194420-17-2.mol

Synonyms:2α,10β-dibenzyloxy-11β-(t-butyldimethylsiloxy)-7β-hydroxy-1α-(p-methoxybenzyloxy)-8β,15,15-trimethyl-4-methylene-trans-bicyclo[6.4.0]dodecan-9-one

Chemical Property of 2α,10β-dibenzyloxy-11β-(t-butyldimethylsiloxy)-7β-hydroxy-1α-(p-methoxybenzyloxy)-8β,15,15-trimethyl-4-methylene-trans-bicyclo[6.4.0]dodecan-9-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2α,10β-dibenzyloxy-11β-(t-butyldimethylsiloxy)-7β-hydroxy-1α-(p-methoxybenzyloxy)-8β,15,15-trimethyl-4-methylene-trans-bicyclo[6.4.0]dodecan-9-one

There total 10 articles about 2α,10β-dibenzyloxy-11β-(t-butyldimethylsiloxy)-7β-hydroxy-1α-(p-methoxybenzyloxy)-8β,15,15-trimethyl-4-methylene-trans-bicyclo[6.4.0]dodecan-9-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: 90.0%

4-[(1S,2S,3R,5R,6R,8S)-2,6-Dibenzyloxy-5-(tert-butyldimethylsiloxy)-3-(p-methoxybenzyloxy)-4,4,8-trimethyl-7-oxocyclooctyl]-4-pentenal (194420-16-1) → 2α,10β-dibenzyloxy-11β-(t-butyldimethylsiloxy)-7β-hydroxy-1α-(p-methoxybenzyloxy)-8β,15,15-trimethyl-4-methylene-trans-bicyclo[6.4.0]dodecan-9-one (194420-17-2) + (1S,3R,4R,6R,7S,8R,12R)-3,7-Dibenzyloxy-4-(tert-butyldimethylsiloxy)-12-hydroxy-6-(p-methoxybenzyloxy)-1,5,5-trimethyl-9-methylenebicyclo[6.4.0]dodecan-2-one (194420-18-3)

Guidance literature:

With sodium methylate; In methanol; at 0 ℃; for 1h;

DOI:10.1002/(sici)1521-3765(19990104)5:1<121::aid-chem121>3.3.co;2-f

Reference yield: 75.0%

(1S,3R,4R,6R,7S,8R,12R)-3,7-Dibenzyloxy-4-(tert-butyldimethylsiloxy)-12-hydroxy-6-(p-methoxybenzyloxy)-1,5,5-trimethyl-9-methylenebicyclo[6.4.0]dodecan-2-one (194420-18-3) → 2α,10β-dibenzyloxy-11β-(t-butyldimethylsiloxy)-7β-hydroxy-1α-(p-methoxybenzyloxy)-8β,15,15-trimethyl-4-methylene-trans-bicyclo[6.4.0]dodecan-9-one (194420-17-2)

Guidance literature:

With sodium methylate; In methanol; at 0 - 20 ℃; for 1.08333h;

DOI:10.1002/(sici)1521-3765(19990104)5:1<121::aid-chem121>3.3.co;2-f

Reference yield:

2-bromo-5-(triethylsilyloxy)pentene (178626-24-9) → 2α,10β-dibenzyloxy-11β-(t-butyldimethylsiloxy)-7β-hydroxy-1α-(p-methoxybenzyloxy)-8β,15,15-trimethyl-4-methylene-trans-bicyclo[6.4.0]dodecan-9-one (194420-17-2)

Guidance literature:

Multi-step reaction with 4 steps

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

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

1.3: 92 percent / diethyl ether; pentane / 1.33 h / -23 °C

2.1: 97 percent / HCl; H₂O / tetrahydrofuran / 0.83 h / 0 °C

3.1: 92 percent / NMO; TPAP; molecular sieves 4 Angstroem / CH₂Cl₂ / 0.5 h / 0 °C

4.1: 90 percent / MeONa / methanol / 1 h / 0 °C

With hydrogenchloride; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; water; tert.-butyl lithium; sodium methylate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; pentane; 1.1: Metallation / 1.2: Substitution / 1.3: Addition / 2.1: Hydrolysis / 3.1: Oxidation / 4.1: Cycloaddition;

DOI:10.1002/(sici)1521-3765(19990104)5:1<121::aid-chem121>3.3.co;2-f

upstream raw materials:

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

(1S,3R,4R,6R,7S,8R,12R)-3,7-Dibenzyloxy-4-(tert-butyldimethylsiloxy)-12-hydroxy-6-(p-methoxybenzyloxy)-1,5,5-trimethyl-9-methylenebicyclo[6.4.0]dodecan-2-one

4-bromopent-4-en-1-ol

ethyl 4-bromo-4-pentenoate

Downstream raw materials:

[(3aS,6aR,7S,8R,10R,11S,11aR,11bS)-7,11-Bis-benzyloxy-8-(4-methoxy-benzyloxy)-2,2,9,9,11b-pentamethyl-6-methylene-dodecahydro-1,3-dioxa-cycloocta[de]naphthalen-10-yloxy]-tert-butyl-dimethyl-silane

(3aS,6aR,7S,8S,11S,11aR,11bS)-7,11-Bis-benzyloxy-8-(ethyl-dimethyl-silanyloxy)-2,2,9,9,11b-pentamethyl-6-methylene-8-(2-oxo-propyl)-decahydro-1,3-dioxa-cycloocta[de]naphthalen-10-one

(3aS,6aR,7S,8S,11S,11aR,11bS)-8-Allyl-7,11-bis-benzyloxy-8-(ethyl-dimethyl-silanyloxy)-2,2,9,9,11b-pentamethyl-6-methylene-decahydro-1,3-dioxa-cycloocta[de]naphthalen-10-one

C₃₉H₅₄O₆Si