(2S,3R,4R,4aα,8aβ)-3,4,4a,5,6,7,8,8a-Octahydro-2β,7β-dihydroxy-4-[(Z)-3-hydroxy-1-oxo-2-propenyl]-2α,4,5α,7α-tetramethyl-3-[(R)-1-methylpropyl]-1(2H)-naphthalenone

Base Information

Chemical Name:(2S,3R,4R,4aα,8aβ)-3,4,4a,5,6,7,8,8a-Octahydro-2β,7β-dihydroxy-4-[(Z)-3-hydroxy-1-oxo-2-propenyl]-2α,4,5α,7α-tetramethyl-3-[(R)-1-methylpropyl]-1(2H)-naphthalenone
CAS No.:85269-25-6
Molecular Formula:C₂₁H₃₄O₅
Molecular Weight:366.498
Hs Code.:
Mol file:85269-25-6.mol

(2S,3R,4R,4aα,8aβ)-3,4,4a,5,6,7,8,8a-Octahydro-2β,7β-dihydroxy-4-[(Z)-3-hydroxy-1-oxo-2-propenyl]-2α,4,5α,7α-tetramethyl-3-[(R)-1-methylpropyl]-1(2H)-naphthalenone

Synonyms:betaenone C;

Suppliers and Price of (2S,3R,4R,4aα,8aβ)-3,4,4a,5,6,7,8,8a-Octahydro-2β,7β-dihydroxy-4-[(Z)-3-hydroxy-1-oxo-2-propenyl]-2α,4,5α,7α-tetramethyl-3-[(R)-1-methylpropyl]-1(2H)-naphthalenone

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (2S,3R,4R,4aα,8aβ)-3,4,4a,5,6,7,8,8a-Octahydro-2β,7β-dihydroxy-4-[(Z)-3-hydroxy-1-oxo-2-propenyl]-2α,4,5α,7α-tetramethyl-3-[(R)-1-methylpropyl]-1(2H)-naphthalenone

Chemical Property:

PSA：94.83000
LogP:3.04280

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:: SDS file from LookChem

Useful:

Technology Process of (2S,3R,4R,4aα,8aβ)-3,4,4a,5,6,7,8,8a-Octahydro-2β,7β-dihydroxy-4-[(Z)-3-hydroxy-1-oxo-2-propenyl]-2α,4,5α,7α-tetramethyl-3-[(R)-1-methylpropyl]-1(2H)-naphthalenone

There total 24 articles about (2S,3R,4R,4aα,8aβ)-3,4,4a,5,6,7,8,8a-Octahydro-2β,7β-dihydroxy-4-[(Z)-3-hydroxy-1-oxo-2-propenyl]-2α,4,5α,7α-tetramethyl-3-[(R)-1-methylpropyl]-1(2H)-naphthalenone 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: 74.0%

: 85269-23-4
betaenone B

: 85269-25-6
(-)-betaenone C

Guidance literature:: With Dess-Martin periodane; In dichloromethane; at 20 ℃; for 2h;
DOI:10.1002/chem.201904360

Reference yield:

: 106-25-2
Nerol

: 85269-25-6
(-)-betaenone C

Guidance literature:: Multi-step reaction with 20 steps

1: Sharpless oxidation

3: 60 percent / imidazole / dimethylformamide / Ambient temperature

4: LDA / tetrahydrofuran / -40 °C

5: 91 percent / LiAlH₄ / tetrahydrofuran / 1.5 h / -50 °C

6: pyridine / 36 h / Ambient temperature

7: Pr₂NEt / 24 h / Ambient temperature

8: n-Bu₄NF / tetrahydrofuran / 3.5 h / 0 °C

9: n-Bu₃P / pyridine / 24 h / Ambient temperature

10: 99.7 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 14 h / -20 - -10 °C

12: SiO₂ / benzene / 36 h / Ambient temperature

13: oxalyl chloride / dimethylsulfoxide / 0.33 h / -55 °C

14: 46.8 percent / BuLi / 40 h / -4 - -3 °C

15: 40.5 percent / toluene / 36 h / 115 °C / sealed tube

16: 66.1 percent / OsO₄ / pyridine; diethyl ether / 3 h / -30 °C

17: 65.3 percent / PCC, NaOAc / CH₂Cl₂ / 1 h / Ambient temperature

18: 91.7 percent / AlCl₃, NaI / acetonitrile; CH₂Cl₂ / 30 h / 20 °C

19: 34 percent / AlCl₃, EtSH / 4 h / -8 °C

With 1H-imidazole; osmium(VIII) oxide; lithium aluminium tetrahydride; n-butyllithium; aluminium trichloride; oxalyl dichloride; dipropylethylamine; tributylphosphine; tetrabutyl ammonium fluoride; sodium acetate; silica gel; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; ethanethiol; sodium iodide; lithium diisopropyl amide; In tetrahydrofuran; pyridine; diethyl ether; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; acetonitrile; benzene;
DOI:10.1016/S0040-4039(01)80742-5

Reference yield:

: 127760-69-4
(2E, 4R)-2,4-dimethyl-2-hexen-1-ol

: 85269-25-6
(-)-betaenone C

Guidance literature:: Multi-step reaction with 11 steps

1: PCC / CH₂Cl₂ / 0.5 h / 0 - 25 °C

3: SiO₂ / benzene / 36 h / Ambient temperature

4: oxalyl chloride / dimethylsulfoxide / 0.33 h / -55 °C

5: 46.8 percent / BuLi / 40 h / -4 - -3 °C

6: 40.5 percent / toluene / 36 h / 115 °C / sealed tube

7: 66.1 percent / OsO₄ / pyridine; diethyl ether / 3 h / -30 °C

8: 65.3 percent / PCC, NaOAc / CH₂Cl₂ / 1 h / Ambient temperature

9: 91.7 percent / AlCl₃, NaI / acetonitrile; CH₂Cl₂ / 30 h / 20 °C

10: 34 percent / AlCl₃, EtSH / 4 h / -8 °C

With osmium(VIII) oxide; n-butyllithium; aluminium trichloride; oxalyl dichloride; sodium acetate; silica gel; pyridinium chlorochromate; ethanethiol; sodium iodide; In pyridine; diethyl ether; dichloromethane; dimethyl sulfoxide; toluene; acetonitrile; benzene;
DOI:10.1016/S0040-4039(01)80742-5