(3S,3aS,6aS,10S,10aR)-10-Hydroxy-3-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyloxy)-7,7-dimethyl-1-oxo-3,3a,6,6a,7,8,9,10-octahydro-2-oxa-cyclopenta[d]naphthalene-4-carbaldehyde

Base Information

Chemical Name:(3S,3aS,6aS,10S,10aR)-10-Hydroxy-3-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyloxy)-7,7-dimethyl-1-oxo-3,3a,6,6a,7,8,9,10-octahydro-2-oxa-cyclopenta[d]naphthalene-4-carbaldehyde
CAS No.:330998-95-3
Molecular Formula:C₂₅H₃₈O₅
Molecular Weight:418.574
Hs Code.:

(3S,3aS,6aS,10S,10aR)-10-Hydroxy-3-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyloxy)-7,7-dimethyl-1-oxo-3,3a,6,6a,7,8,9,10-octahydro-2-oxa-cyclopenta[d]naphthalene-4-carbaldehyde

Synonyms:(3S,3aS,6aS,10S,10aR)-10-Hydroxy-3-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyloxy)-7,7-dimethyl-1-oxo-3,3a,6,6a,7,8,9,10-octahydro-2-oxa-cyclopenta[d]naphthalene-4-carbaldehyde

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Chemical Property of (3S,3aS,6aS,10S,10aR)-10-Hydroxy-3-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyloxy)-7,7-dimethyl-1-oxo-3,3a,6,6a,7,8,9,10-octahydro-2-oxa-cyclopenta[d]naphthalene-4-carbaldehyde

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Technology Process of (3S,3aS,6aS,10S,10aR)-10-Hydroxy-3-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyloxy)-7,7-dimethyl-1-oxo-3,3a,6,6a,7,8,9,10-octahydro-2-oxa-cyclopenta[d]naphthalene-4-carbaldehyde

There total 13 articles about (3S,3aS,6aS,10S,10aR)-10-Hydroxy-3-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyloxy)-7,7-dimethyl-1-oxo-3,3a,6,6a,7,8,9,10-octahydro-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: 72.0%

: 330998-94-2
4-Nitro-benzoic acid (3S,3aS,6aS,10S,10aR)-4-formyl-3-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyloxy)-7,7-dimethyl-1-oxo-3,3a,6,6a,7,8,9,10-octahydro-2-oxa-cyclopenta[d]naphthalen-10-yl ester

: 330998-95-3
(3S,3aS,6aS,10S,10aR)-10-Hydroxy-3-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyloxy)-7,7-dimethyl-1-oxo-3,3a,6,6a,7,8,9,10-octahydro-2-oxa-cyclopenta[d]naphthalene-4-carbaldehyde

Guidance literature:: With potassium carbonate; In methanol; at 20 ℃; for 1h;
DOI:10.1002/1099-0690(200102)2001:3<473::AID-EJOC473>3.0.CO;2-J

Reference yield:

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

: 330998-95-3
(3S,3aS,6aS,10S,10aR)-10-Hydroxy-3-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyloxy)-7,7-dimethyl-1-oxo-3,3a,6,6a,7,8,9,10-octahydro-2-oxa-cyclopenta[d]naphthalene-4-carbaldehyde

Guidance literature:: Multi-step reaction with 13 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 / 4 h / 0 °C

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

6.1: 88 percent / Li(SePh) / tetrahydrofuran / 6 h / -60 °C

7.1: 68 percent / xylene / 60 h / 140 °C

8.1: 95 percent / DMAP / 4 h / 20 °C

9.1: 49.8 percent / KNO₂; 18-crown-6 / dimethylformamide / 12 h / 40 - 50 °C

10.1: 98 percent / DCC; DMAP / 3 h / 20 °C

11.1: 83 percent / TBAF / tetrahydrofuran / 2 h / 20 °C

12.1: 62 percent / SO₃*py; Et₃N / dimethylsulfoxide / 18 h / 20 °C

13.1: 72 percent / K₂CO₃ / methanol / 1 h / 20 °C

With 1H-imidazole; dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; 9-borabicyclo[3.3.1]nonane dimer; potassium nitrite; 18-crown-6 ether; pyridine-SO₃ complex; [bis(acetoxy)iodo]benzene; lithium phenylselenide; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; potassium carbonate; triethylamine; dicyclohexyl-carbodiimide; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; diethyl ether; dimethyl sulfoxide; N,N-dimethyl-formamide; xylene; 1.1: Horner-Emmons reaction / 7.1: intramolecular Diels-Alder reaction / 12.1: Parikh-Doering oxidation;
DOI:10.1002/1099-0690(200102)2001:3<473::AID-EJOC473>3.0.CO;2-J

Reference yield:

: 248250-07-9
(2E,4E)-6,6-Dimethyl-nona-2,4,8-trienoic acid methyl ester

: 330998-95-3
(3S,3aS,6aS,10S,10aR)-10-Hydroxy-3-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyloxy)-7,7-dimethyl-1-oxo-3,3a,6,6a,7,8,9,10-octahydro-2-oxa-cyclopenta[d]naphthalene-4-carbaldehyde

Guidance literature:: Multi-step reaction with 12 steps

1.1: 98 percent / DIBALH / diethyl ether / 0.5 h / 0 °C

2.1: 100 percent / imidazole / dimethylformamide / 2 h / 20 °C

3.1: 9-BBN / tetrahydrofuran / 4 h / 20 °C

3.2: 91 percent / H₂O₂; NaOH / ethanol / 4 h / 0 °C

4.1: 98 percent / TEMPO; PhI(OAc)2 / 2 h / 20 °C

5.1: 88 percent / Li(SePh) / tetrahydrofuran / 6 h / -60 °C

6.1: 68 percent / xylene / 60 h / 140 °C

7.1: 95 percent / DMAP / 4 h / 20 °C

8.1: 49.8 percent / KNO₂; 18-crown-6 / dimethylformamide / 12 h / 40 - 50 °C

9.1: 98 percent / DCC; DMAP / 3 h / 20 °C

10.1: 83 percent / TBAF / tetrahydrofuran / 2 h / 20 °C

11.1: 62 percent / SO₃*py; Et₃N / dimethylsulfoxide / 18 h / 20 °C

12.1: 72 percent / K₂CO₃ / methanol / 1 h / 20 °C

With 1H-imidazole; dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; 9-borabicyclo[3.3.1]nonane dimer; potassium nitrite; 18-crown-6 ether; pyridine-SO₃ complex; [bis(acetoxy)iodo]benzene; lithium phenylselenide; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; potassium carbonate; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; diethyl ether; dimethyl sulfoxide; N,N-dimethyl-formamide; xylene; 6.1: intramolecular Diels-Alder reaction / 11.1: Parikh-Doering oxidation;
DOI:10.1002/1099-0690(200102)2001:3<473::AID-EJOC473>3.0.CO;2-J