(3S,3aS,4S,6aS,10aR)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-3-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyloxy)-7,7-dimethyl-3a,4,6a,7,8,9-hexahydro-3H-2-oxa-cyclopenta[d]naphthalene-1,10-dione

Base Information

• Chemical Name: (3S,3aS,4S,6aS,10aR)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-3-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyloxy)-7,7-dimethyl-3a,4,6a,7,8,9-hexahydro-3H-2-oxa-cyclopenta[d]naphthalene-1,10-dione
• CAS No.: 303780-20-3
• Molecular Formula: C₄₁H₅₆O₅Si
• Molecular Weight: 656.978
• Mol file: 303780-20-3.mol

Synonyms:(3S,3aS,4S,6aS,10aR)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-3-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyloxy)-7,7-dimethyl-3a,4,6a,7,8,9-hexahydro-3H-2-oxa-cyclopenta[d]naphthalene-1,10-dione

Chemical Property of (3S,3aS,4S,6aS,10aR)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-3-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyloxy)-7,7-dimethyl-3a,4,6a,7,8,9-hexahydro-3H-2-oxa-cyclopenta[d]naphthalene-1,10-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,3aS,4S,6aS,10aR)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-3-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyloxy)-7,7-dimethyl-3a,4,6a,7,8,9-hexahydro-3H-2-oxa-cyclopenta[d]naphthalene-1,10-dione

There total 10 articles about (3S,3aS,4S,6aS,10aR)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-3-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyloxy)-7,7-dimethyl-3a,4,6a,7,8,9-hexahydro-3H-2-oxa-cyclopenta[d]naphthalene-1,10-dione 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: 95.0%

(3S,3aS,4S,6aS,10R,10aR)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-10-hydroxy-3-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyloxy)-7,7-dimethyl-3,3a,4,6a,7,8,9,10-octahydro-2-oxa-cyclopenta[d]naphthalen-1-one (248250-13-7) → (3S,3aS,4S,6aS,10aR)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-3-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyloxy)-7,7-dimethyl-3a,4,6a,7,8,9-hexahydro-3H-2-oxa-cyclopenta[d]naphthalene-1,10-dione (303780-20-3)

Guidance literature:

With dipyridinium dichromate; 3 A molecular sieve; for 2h;

DOI:10.1002/1521-3773(20000804)39:15<2764::AID-ANIE2764>3.0.CO;2-S

Reference yield: 79.0%

(S)-3-[(5E,7E)-(R)-9-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxy-4,4-dimethyl-nona-5,7-dienyl]-5-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyloxy)-5H-furan-2-one (248250-12-6) → (3S,3aS,4S,6aS,10aR)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-3-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyloxy)-7,7-dimethyl-3a,4,6a,7,8,9-hexahydro-3H-2-oxa-cyclopenta[d]naphthalene-1,10-dione (303780-20-3) + (3R,3aR,4R,6aR,10aS)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-3-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyloxy)-7,7-dimethyl-3a,4,6a,7,8,9-hexahydro-3H-2-oxa-cyclopenta[d]naphthalene-1,10-dione

Guidance literature:

With 2,6-dimethylpyridine; Dess-Martin periodane; In dichloromethane; at 20 ℃; for 16h;

DOI:10.1016/S0957-4166(00)00286-X

Reference yield:

2,2-dimethyl-4-pentenal (5497-67-6) → (3S,3aS,4S,6aS,10aR)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-3-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyloxy)-7,7-dimethyl-3a,4,6a,7,8,9-hexahydro-3H-2-oxa-cyclopenta[d]naphthalene-1,10-dione (303780-20-3)

Guidance literature:

Multi-step reaction with 9 steps

1: 85 percent / LiHMDS / tetrahydrofuran / -40 °C

2: 97 percent / DIBALH / diethyl ether / 0.5 h / 0 °C

3: 100 percent / imidazole / dimethylformamide / 2 h / 20 °C

4: tetrahydrofuran / 4 h / 20 °C

5: H₂O₂; NaOH / ethanol / 4 h / 0 °C

6: 98 percent / TEMPO; diacetoxyiodobenzene / CH₂Cl₂ / 1.5 h / 20 °C

7: 88 percent / PhSeLi / tetrahydrofuran / 6 h / -60 °C

8: 68 percent / xylene / 60 h / 140 °C

9: 95 percent / PDC; molecular sieves 3 Angstroem / 2 h

With 1H-imidazole; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hydroxide; dipyridinium dichromate; [bis(acetoxy)iodo]benzene; 3 A molecular sieve; lithium phenylselenide; dihydrogen peroxide; diisobutylaluminium hydride; lithium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; xylene; 1: Horner-Wadsworth-Emmons reaction / 2: Reduction / 3: Etherification / 4: Addition / 5: Oxidation / 6: Oxidation / 7: tandem Michael-aldol-retro-Michael reaction / 8: Cyclization / 9: Oxidation;

DOI:10.1002/1521-3773(20000804)39:15<2764::AID-ANIE2764>3.0.CO;2-S

upstream raw materials:

(S)-3-[(5E,7E)-(R)-9-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxy-4,4-dimethyl-nona-5,7-dienyl]-5-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyloxy)-5H-furan-2-one

(3S,3aS,4S,6aS,10R,10aR)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-10-hydroxy-3-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyloxy)-7,7-dimethyl-3,3a,4,6a,7,8,9,10-octahydro-2-oxa-cyclopenta[d]naphthalen-1-one

2,2-dimethyl-4-pentenal

(2E,4E)-6,6-dimethyl-2,4,8-nonatrien-1-ol

Downstream raw materials:

(3S,3aS,4S,6aS,10aR)-4-Hydroxymethyl-3-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyloxy)-7,7-dimethyl-3a,4,6a,7,8,9-hexahydro-3H-2-oxa-cyclopenta[d]naphthalene-1,10-dione