[1S,(+)]-1,2,3,4,4a,9,10,10aα-Octahydro-6-hydroxy-1,4aβ-dimethyl-7-(1-methylethyl)-1β-phenanthrenecarboxylic acid

Base Information

• Chemical Name: [1S,(+)]-1,2,3,4,4a,9,10,10aα-Octahydro-6-hydroxy-1,4aβ-dimethyl-7-(1-methylethyl)-1β-phenanthrenecarboxylic acid
• CAS No.: 55051-96-2
• Molecular Formula: C20H28O3
• Molecular Weight: 316.43
• Mol file: 55051-96-2.mol

Synonyms:Lambertsaeure;13-Isopropyl-podocarpsaeure;lambertic acid;12-Hydroxy-abieta-8,11,13-trien-19-oic Acid;

Chemical Property of [1S,(+)]-1,2,3,4,4a,9,10,10aα-Octahydro-6-hydroxy-1,4aβ-dimethyl-7-(1-methylethyl)-1β-phenanthrenecarboxylic acid

Chemical Property:

• Melting Point: 252-254℃
• PSA: 57.53000
• Density: 1.121±0.06 g/cm3 (20 ºC 760 Torr)
• LogP: 4.61050

Purity/Quality:

98%Min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of [1S,(+)]-1,2,3,4,4a,9,10,10aα-Octahydro-6-hydroxy-1,4aβ-dimethyl-7-(1-methylethyl)-1β-phenanthrenecarboxylic acid

There total 28 articles about [1S,(+)]-1,2,3,4,4a,9,10,10aα-Octahydro-6-hydroxy-1,4aβ-dimethyl-7-(1-methylethyl)-1β-phenanthrenecarboxylic 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: 83.0%

methyl O-methyl-13-isopropylpodocarpate (24035-61-8,30905-78-3,57745-84-3,94669-26-8,111583-88-1) → (1S,4aS)-6-Hydroxy-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene-1-carboxylic acid (55051-96-2,116032-84-9)

Guidance literature:

With boron tribromide; In dichloromethane; at -10 ℃; for 1h;

DOI:10.1139/v87-132

Reference yield: 82.0%

methyl (+)-12-methoxyabieta-8,11,13-trien-19-oate (24035-61-8) → lambertic acid (116032-84-9,55051-96-2)

Guidance literature:

With aluminium trichloride; ethanethiol;

DOI:10.1016/S0040-4039(00)99343-2

Reference yield:

(S)-(-)-2-Methyl-2-(2'-nitrovinyl)-δ-valerolactone (102631-75-4) → lambertic acid (116032-84-9,55051-96-2)

Guidance literature:

Multi-step reaction with 11 steps

1: 364 mg / tetrahydrofuran / 2 h / -78 °C

2: 100 percent / NaOMe / 8 h / Ambient temperature

3: Et₃N / CH₂Cl₂ / 1 h / 0 °C

4: NaI / acetone / 1.) room temperature, 10 h, 2.) reflux, 3 h

5: 56 percent / NaH / dimethylformamide / 14 h / 0 °C

6: 1.) NaOMe, 2.) TiCl₃, NH₄OAc / 1.) MeOH, room temperature, 1 h, 2.) H₂O, room temperature, 2 h

7: 85 percent / TiCl₄, Zn / tetrahydrofuran; CH₂Cl₂ / 1 h / Ambient temperature

8: 92 percent / P₂O₅, MeSO₃H / 0.25 h / Ambient temperature

10: 92 percent / Et₃SiH, CF₃CO₂H / CH₂Cl₂ / 8 h / Ambient temperature

11: 82 percent / AlCl₃, EtSH / 24 h / Ambient temperature

With triethylsilane; aluminium trichloride; titanium(III) chloride; methanesulfonic acid; ammonium acetate; sodium methylate; phosphorus pentoxide; titanium tetrachloride; sodium hydride; triethylamine; trifluoroacetic acid; ethanethiol; sodium iodide; zinc; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetone;

DOI:10.1039/P19920001505

upstream raw materials:

methyl (+)-12-methoxyabieta-8,11,13-trien-19-oate

12-methoxy-abietatrien-(8.11.13)-oic acid-⁽¹⁹⁾

methyl O-methylpodocarpate

methyl 13-α-hydroxyisopropyl-12-methoxypodocarpa-8,11,13-trien-19-oate

Refernces

• 1、 Wu, Xiongyu,Silver? Ejneby, Malin,Ottosson, Nina E,Elinder, Fredrik,Konradsson, Peter. "A Suzuki–Miyaura Coupling of ortho-Hydroxyaryl Bromide with Isopropenylboronic Pinacol Ester: Synthesis of the Potassium-Channel Opener (+)-Callitrisic Acid". . p. 1730 - 1734. Retrieved 2018/04/24.
• 2、 Node, Manabu,Hao, Xiao-jiang,Nagasawa, Hideko,Fuji, Kaoru. "GENERAL ENTRY TO THE SYNTHESIS OF OPTICALLY ACTIVE DITERPENOIDS OF C-20β SERIES". . p. 4141 - 4144. Retrieved 2007/10/02.