2-[[(2S,4aS,6aR,6aS,6bR,8aR,12aR,14bR)-10-(2-carboxybenzoyl)oxy-2,4a,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicen-2-yl]methoxycarbonyl]benzoic acid

Base Information

• Chemical Name: 2-[[(2S,4aS,6aR,6aS,6bR,8aR,12aR,14bR)-10-(2-carboxybenzoyl)oxy-2,4a,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicen-2-yl]methoxycarbonyl]benzoic acid
• CAS No.: 102416-27-3
• Molecular Formula: C46H58 O8
• Molecular Weight: 738.962
• DSSTox Substance ID: DTXSID60907485
• Mol file: 102416-27-3.mol

Synonyms:18-olean-12-ene-3,30-diol dihemiphthalate;deoxoglycyrrhetol dihemiphthalate;DGDH;di-Na salt (3beta,18alpha,20beta)-isomer of deoxoglycyrrhetol dihemiphthalate;di-Na salt (3beta,20beta)-isomer of deoxoglycyrrhetol dihemiphthalate

Chemical Property of 2-[[(2S,4aS,6aR,6aS,6bR,8aR,12aR,14bR)-10-(2-carboxybenzoyl)oxy-2,4a,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicen-2-yl]methoxycarbonyl]benzoic acid

Chemical Property:

• Vapor Pressure: 5.95E-27mmHg at 25°C
• Boiling Point: 799.2°Cat760mmHg
• Flash Point: 231.8°C
• PSA: 127.20000
• Density: 1.23g/cm³
• LogP: 10.26710
• XLogP3: 11.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 9
• Exact Mass: 738.41316880
• Heavy Atom Count: 54
• Complexity: 1550

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C2CCC3(C(C2(CCC1OC(=O)C4=CC=CC=C4C(=O)O)C)CC=C5C3(CCC6(C5CC(CC6)(C)COC(=O)C7=CC=CC=C7C(=O)O)C)C)C)C
• Isomeric SMILES: C[C@]12CC[C@](C[C@H]1C3=CC[C@@H]4[C@]5(CCC(C([C@@H]5CC[C@]4([C@@]3(CC2)C)C)(C)C)OC(=O)C6=CC=CC=C6C(=O)O)C)(C)COC(=O)C7=CC=CC=C7C(=O)O

Technology Process of 2-[[(2S,4aS,6aR,6aS,6bR,8aR,12aR,14bR)-10-(2-carboxybenzoyl)oxy-2,4a,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicen-2-yl]methoxycarbonyl]benzoic acid

There total 5 articles about 2-[[(2S,4aS,6aR,6aS,6bR,8aR,12aR,14bR)-10-(2-carboxybenzoyl)oxy-2,4a,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicen-2-yl]methoxycarbonyl]benzoic 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:

phthalic anhydride (85-44-9) + 11-hydroxymethyl-4,4a,6a,6b,8a,11,14b-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-eicosahydropicen-3-ol (6813-59-8) → deoxoglycyrrhetol 3β,30-dihemiphthalate (102416-27-3)

Guidance literature:

With triethylamine; In pyridine; at 90 - 100 ℃; for 7h;

DOI:10.1248/cpb.35.1910

Reference yield:

enoxolone (471-53-4) → deoxoglycyrrhetol 3β,30-dihemiphthalate (102416-27-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 660 mg / NaAlH₂(OCH₂CH₂OCH₃)2 / tetrahydrofuran; toluene / 1 h / 60 °C

2: 500 mg / NaHCO₃/H₂ / 10percent Pd-C / ethanol

3: 20.5 g / triethylamine / pyridine / 7 h / 90 - 100 °C

With hydrogen; sodium hydrogencarbonate; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; palladium on activated charcoal; In tetrahydrofuran; pyridine; ethanol; toluene;

DOI:10.1248/cpb.35.1910

Reference yield:

18β-olean-12-ene-3β,11β,30-triol (13947-06-3) → deoxoglycyrrhetol 3β,30-dihemiphthalate (102416-27-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 500 mg / NaHCO₃/H₂ / 10percent Pd-C / ethanol

2: 20.5 g / triethylamine / pyridine / 7 h / 90 - 100 °C

With hydrogen; sodium hydrogencarbonate; triethylamine; palladium on activated charcoal; In pyridine; ethanol;

DOI:10.1248/cpb.35.1910

upstream raw materials:

phthalic anhydride

11-hydroxymethyl-4,4a,6a,6b,8a,11,14b-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-eicosahydropicen-3-ol

enoxolone

18β-olean-12-ene-3β,11β,30-triol

Downstream raw materials:

disodium 18β-olean-12-ene-3β,30-diol di-O-hemiphthalate