(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
Hs Code.:

(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

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

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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

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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%

: 303780-20-3
(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

: 303780-21-4
(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

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%

: 5497-67-6
2,2-dimethyl-4-pentenal

: 122079-41-8
(5S)-(D-menthyloxy)-2(5H)-furanone

: 113661-09-9
trans-4-bromo-2-buten-1-ol

: 303780-21-4
(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

Guidance literature:: Multistep reaction;
DOI:10.1055/s-2001-9714

Reference yield:

: 5497-67-6
2,2-dimethyl-4-pentenal

: 303780-21-4
(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

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