(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

Base Information

• Chemical Name: (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
• CAS No.: 329897-87-2
• Molecular Formula: C₂₅H₃₆O₄
• Molecular Weight: 400.558

Synonyms:(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

Chemical Property of (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

Chemical Property:

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Technology Process of (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

There total 11 articles about (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 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: 79.0%

(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) → (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 (329897-87-2)

Guidance literature:

With sulfur trioxide pyridine complex; triethylamine; In dimethyl sulfoxide; at 20 ℃;

DOI:10.1055/s-2001-9711

Reference yield:

2,2-dimethyl-4-pentenal (5497-67-6) → (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 (329897-87-2)

Guidance literature:

Multi-step reaction with 11 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

11.1: 79 percent / pyridine*SO₃; Et₃N / dimethylsulfoxide / 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; sulfur trioxide pyridine complex; diisobutylaluminium hydride; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; dimethyl sulfoxide; N,N-dimethyl-formamide; xylene; 1.1: Horner-Emmons reaction / 6.1: Baylis-Hillman reaction / 7.1: Intramolecular Diels-Alder reaction / 11.1: Parikh-Doering oxidation;

DOI:10.1055/s-2001-9711

Reference yield:

(2E,4E)-6,6-dimethyl-2,4,8-nonatrien-1-ol (248250-08-0) → (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 (329897-87-2)

Guidance literature:

Multi-step reaction with 9 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

9.1: 79 percent / pyridine*SO₃; Et₃N / dimethylsulfoxide / 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; sulfur trioxide pyridine complex; triethylamine; In tetrahydrofuran; dimethyl sulfoxide; N,N-dimethyl-formamide; xylene; 4.1: Baylis-Hillman reaction / 5.1: Intramolecular Diels-Alder reaction / 9.1: Parikh-Doering oxidation;

DOI:10.1055/s-2001-9711

upstream raw materials:

(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

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

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