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

Base Information

• Chemical Name: (3S,3aS,4S,6aS,10aR)-4-Hydroxymethyl-3-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyloxy)-7,7-dimethyl-3,3a,4,6a,7,8-hexahydro-2-oxa-cyclopenta[d]naphthalen-1-one
• CAS No.: 329897-86-1
• Molecular Formula: C₂₅H₃₈O₄
• Molecular Weight: 402.574
• Mol file: 329897-86-1.mol

Synonyms:(3S,3aS,4S,6aS,10aR)-4-Hydroxymethyl-3-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyloxy)-7,7-dimethyl-3,3a,4,6a,7,8-hexahydro-2-oxa-cyclopenta[d]naphthalen-1-one

Chemical Property of (3S,3aS,4S,6aS,10aR)-4-Hydroxymethyl-3-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyloxy)-7,7-dimethyl-3,3a,4,6a,7,8-hexahydro-2-oxa-cyclopenta[d]naphthalen-1-one

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-3,3a,4,6a,7,8-hexahydro-2-oxa-cyclopenta[d]naphthalen-1-one

There total 10 articles about (3S,3aS,4S,6aS,10aR)-4-Hydroxymethyl-3-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyloxy)-7,7-dimethyl-3,3a,4,6a,7,8-hexahydro-2-oxa-cyclopenta[d]naphthalen-1-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%

(3S,3aS,4S,6aS,10aR)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-3-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyloxy)-7,7-dimethyl-3,3a,4,6a,7,8-hexahydro-2-oxa-cyclopenta[d]naphthalen-1-one (329897-84-9) → (3S,3aS,4S,6aS,10aR)-4-Hydroxymethyl-3-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyloxy)-7,7-dimethyl-3,3a,4,6a,7,8-hexahydro-2-oxa-cyclopenta[d]naphthalen-1-one (329897-86-1)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 2h;

DOI:10.1055/s-2001-9711

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-3,3a,4,6a,7,8-hexahydro-2-oxa-cyclopenta[d]naphthalen-1-one (329897-86-1)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 85 percent / LiHMDS / tetrahydrofuran / -40 °C

2.1: 98 percent / DIBALH / diethyl ether / 0.5 h / 0 °C

3.1: 100 percent / imidazole / dimethylformamide / 2 h / 20 °C

4.1: 9-BBN / tetrahydrofuran / 4 h / 20 °C

4.2: 91 percent / H₂O₂; NaOH / ethanol / 1 h / 0 °C

5.1: 98 percent / TEMPO; PhI(OAc)2 / 2 h / 20 °C

6.1: 88 percent / PhSeLi / tetrahydrofuran / 6 h / -60 °C

7.1: 69 percent / xylene / 60 h / 140 °C

8.1: 98 percent / DMAP / 2 h / 0 °C

9.1: 84 percent / 2,6-lutidine / 4 h / 100 °C

10.1: 90 percent / TBAF / tetrahydrofuran / 2 h / 20 °C

With 1H-imidazole; 2,6-dimethylpyridine; dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; 9-borabicyclo[3.3.1]nonane dimer; [bis(acetoxy)iodo]benzene; lithium phenylselenide; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; lithium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide; xylene; 1.1: Horner-Emmons reaction / 6.1: Baylis-Hillman reaction / 7.1: Intramolecular Diels-Alder reaction;

DOI:10.1055/s-2001-9711

Reference yield:

(2E,4E)-6,6-dimethyl-2,4,8-nonatrien-1-ol (248250-08-0) → (3S,3aS,4S,6aS,10aR)-4-Hydroxymethyl-3-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyloxy)-7,7-dimethyl-3,3a,4,6a,7,8-hexahydro-2-oxa-cyclopenta[d]naphthalen-1-one (329897-86-1)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 100 percent / imidazole / dimethylformamide / 2 h / 20 °C

2.1: 9-BBN / tetrahydrofuran / 4 h / 20 °C

2.2: 91 percent / H₂O₂; NaOH / ethanol / 1 h / 0 °C

3.1: 98 percent / TEMPO; PhI(OAc)2 / 2 h / 20 °C

4.1: 88 percent / PhSeLi / tetrahydrofuran / 6 h / -60 °C

5.1: 69 percent / xylene / 60 h / 140 °C

6.1: 98 percent / DMAP / 2 h / 0 °C

7.1: 84 percent / 2,6-lutidine / 4 h / 100 °C

8.1: 90 percent / TBAF / tetrahydrofuran / 2 h / 20 °C

With 1H-imidazole; 2,6-dimethylpyridine; dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; 9-borabicyclo[3.3.1]nonane dimer; [bis(acetoxy)iodo]benzene; lithium phenylselenide; tetrabutyl ammonium fluoride; In tetrahydrofuran; N,N-dimethyl-formamide; xylene; 4.1: Baylis-Hillman reaction / 5.1: Intramolecular Diels-Alder reaction;

DOI:10.1055/s-2001-9711

upstream raw materials:

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

2,2-dimethyl-4-pentenal

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

(2E,4E)-6,6-Dimethyl-nona-2,4,8-trienoic acid methyl ester

Downstream raw materials:

(3S,3aS,6aS,10aR)-3-((1S,2R,5S)-2-Isopropyl-5-methyl-cyclohexyloxy)-7,7-dimethyl-1-oxo-3,3a,6,6a,7,8-hexahydro-2-oxa-cyclopenta[d]naphthalene-4-carbaldehyde