(5R)-5,6,7,8-Tetrahydro-4-hydroxy-8β-[(1S,4E)-6-hydroxy-1,5-dimethyl-4-hexenyl]-5α-methyl-2-naphthalenecarboxylic acid

Base Information

Chemical Name:(5R)-5,6,7,8-Tetrahydro-4-hydroxy-8β-[(1S,4E)-6-hydroxy-1,5-dimethyl-4-hexenyl]-5α-methyl-2-naphthalenecarboxylic acid
CAS No.:65003-68-1
Molecular Formula:
Molecular Weight:332.43
Hs Code.:

Synonyms:(5R)-5,6,7,8-Tetrahydro-4-hydroxy-8β-[(1S,4E)-6-hydroxy-1,5-dimethyl-4-hexenyl]-5α-methyl-2-naphthalenecarboxylic acid;Dihydroxyserrulatic acid

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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 (5R)-5,6,7,8-Tetrahydro-4-hydroxy-8β-[(1S,4E)-6-hydroxy-1,5-dimethyl-4-hexenyl]-5α-methyl-2-naphthalenecarboxylic acid

Chemical Property:

Boiling Point:470.0±45.0 °C(Predicted)
PKA:4.29±0.60(Predicted)
Density:1.135±0.06 g/cm3(Predicted)

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

Useful:

Technology Process of (5R)-5,6,7,8-Tetrahydro-4-hydroxy-8β-[(1S,4E)-6-hydroxy-1,5-dimethyl-4-hexenyl]-5α-methyl-2-naphthalenecarboxylic acid

There total 11 articles about (5R)-5,6,7,8-Tetrahydro-4-hydroxy-8β-[(1S,4E)-6-hydroxy-1,5-dimethyl-4-hexenyl]-5α-methyl-2-naphthalenecarboxylic acid 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: 60.0%

: 65003-61-4
(5S,8R)-4-Acetoxy-8-((E)-(R)-6-acetoxy-1,5-dimethyl-hex-4-enyl)-5-methyl-5,6,7,8-tetrahydro-naphthalene-2-carboxylic acid methyl ester

: 65003-68-1,130274-07-6
(+/-)-dihydroxyserrulatic acid

Guidance literature:: With sodium hydroxide; In methanol; at 70 ℃; for 5h;
DOI:10.1021/ja00014a036

Reference yield:

: 76741-85-0
4-(ethylenedioxy)-5-methoxy-1-oxo-1,2,3,4-tetrahydronaphthalene

: 65003-68-1,130274-07-6
(+/-)-dihydroxyserrulatic acid

Guidance literature:: Multi-step reaction with 9 steps

2: 95 percent / EtSH/NaH / dimethylformamide / 6 h / Heating

3: 95 percent / pyridine, 4-(N,N-dimethylamino)pyridine

4: 1.) 9-BBN, 2.) PdCl₂(dppf), K₂CO₃, H₂O / 1.) THF, RT, 2 h, 2.) THF, DMF, 50 deg C, 16 h

5: DIBAL / CH₂Cl₂ / 3 h / -78 - 0 °C

6: pyridine, 4-(N,N-dimethylamino)pyridine

7: 69 percent / BF₃*OEt₂, HgO / tetrahydrofuran; H₂O / 0.33 h / Ambient temperature

8: 85 percent / MnO₂, AcOH, NaCN / 6 h / Ambient temperature

9: 60 percent / 1 M aq. NaOH / methanol / 5 h / 70 °C

With pyridine; dmap; manganese(IV) oxide; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; boron trifluoride diethyl etherate; sodium cyanide; water; sodium hydride; diisobutylaluminium hydride; potassium carbonate; acetic acid; ethanethiol; mercury(II) oxide; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/ja00014a036

Reference yield:

: 130216-25-0
(5R,8S)-3-[1,3]Dithian-2-yl-8-methyl-5-((R)-1-methyl-allyl)-5,6,7,8-tetrahydro-naphthalen-1-ol

: 65003-68-1,130274-07-6
(+/-)-dihydroxyserrulatic acid

Guidance literature:: Multi-step reaction with 7 steps

1: 95 percent / pyridine, 4-(N,N-dimethylamino)pyridine

2: 1.) 9-BBN, 2.) PdCl₂(dppf), K₂CO₃, H₂O / 1.) THF, RT, 2 h, 2.) THF, DMF, 50 deg C, 16 h

3: DIBAL / CH₂Cl₂ / 3 h / -78 - 0 °C

4: pyridine, 4-(N,N-dimethylamino)pyridine

5: 69 percent / BF₃*OEt₂, HgO / tetrahydrofuran; H₂O / 0.33 h / Ambient temperature

6: 85 percent / MnO₂, AcOH, NaCN / 6 h / Ambient temperature

7: 60 percent / 1 M aq. NaOH / methanol / 5 h / 70 °C

With pyridine; dmap; manganese(IV) oxide; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; boron trifluoride diethyl etherate; sodium cyanide; water; diisobutylaluminium hydride; potassium carbonate; acetic acid; mercury(II) oxide; In tetrahydrofuran; methanol; dichloromethane; water;
DOI:10.1021/ja00014a036