(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

Base Information

• Chemical Name: (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
• CAS No.: 303780-21-4
• Molecular Formula: C₂₅H₃₈O₅
• Molecular Weight: 418.574
• Mol file: 303780-21-4.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 11 articles about (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 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: 93.0%

(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) → (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 (303780-21-4)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 1h;

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

Reference yield: 13.0%

2,2-dimethyl-4-pentenal (5497-67-6) + (5S)-(D-menthyloxy)-2(5H)-furanone (122079-41-8) + trans-4-bromo-2-buten-1-ol (113661-09-9) → (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 (303780-21-4)

Guidance literature:

Multistep reaction;

DOI:10.1055/s-2001-9714

Reference yield:

2,2-dimethyl-4-pentenal (5497-67-6) → (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 (303780-21-4)

Guidance literature:

Multi-step reaction with 10 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

10: 93 percent / TBAF / tetrahydrofuran / 1 h / 20 °C

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; tetrabutyl ammonium fluoride; 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 / 10: Silyl ether cleavage;

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

upstream raw materials:

2,2-dimethyl-4-pentenal

(5S)-(D-menthyloxy)-2(5H)-furanone

trans-4-bromo-2-buten-1-ol

(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