Eriolangin

Base Information

• Chemical Name: Eriolangin
• CAS No.: 52617-35-3
• Molecular Formula: C20H28O6
• Molecular Weight: 364.4327
• Mol file: 52617-35-3.mol

Synonyms:ERIOLANGIN;

Chemical Property of Eriolangin

Chemical Property:

• Vapor Pressure: 7.1E-15mmHg at 25°C
• Boiling Point: 560°Cat760mmHg
• PKA: 14?+-.0.10(Predicted)
• Flash Point: 194.8°C
• PSA: 93.06000
• Density: 1.19g/cm³
• LogP: 2.06340

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Eriolangin

There total 13 articles about Eriolangin 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: 81.0%

(Z)-2-Methyl-but-2-enoic acid (3aR,4S,7aR)-6-formyloxymethyl-5-((S)-4-formyloxy-1-methyl-butyl)-3-methylene-2-oxo-2,3,3a,4,7,7a-hexahydro-benzofuran-4-yl ester (74663-42-6,74663-43-7) → eriolangin (52617-35-3,74708-54-6)

Guidance literature:

With methanol; Dowex 1-X₈ (OH^(1-)); at 0 ℃; for 2h;

DOI:10.1021/ja00538a030

Reference yield:

(Z)-2-methyl-2-butenoic anhydride (94487-74-8) → eriolangin (52617-35-3,74708-54-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 5.0 mg / pyridine, 4-dimethylaminopyridine / tetrahydrofuran / 43 h

2: 81 percent / Dowex 1-X₈ (OH^(1-)), methanol / 2 h / 0 °C

With pyridine; methanol; dmap; Dowex 1-X₈ (OH^(1-)); In tetrahydrofuran;

DOI:10.1021/ja00538a030

Reference yield:

(3aα,5β,8aα,9aα)-3a,6,7,8a,9,9a-hexahydro-5,8a-dimethylnaphtho<2,3-b>furan-2,8(3H,5H)-dione (66365-19-3) → eriolangin (52617-35-3,74708-54-6)

Guidance literature:

Multi-step reaction with 12 steps

1: 1.) N-bromoacetamide, water, 2.) silver oxide / 1) acetone, irradiation, 60 min; 2) dimethoxyethane, reflux, 1 h

2: 64 percent / m-chloroperbenzoic acid, lithium carbonate, 4,4'-thiobis(2-tert-butyl-6-methylphenol) / CH₂Cl₂ / 168 h / Heating

3: 100 percent / aq. sodium hydroxide / tetrahydrofuran / 1 h

4: 94 percent / diborane / tetrahydrofuran / 1) -20 deg C, 3 h; 2) -10 deg C, 3 h; 3) 0 deg C, 3 h; 4) 25 deg C, 4.5 h

5: 76 percent / imidazole / dimethylformamide / 18 h / Ambient temperature

6: 46 percent / thionyl chloride, pyridine / benzene / 0.42 h / Ambient temperature

7: 1.) lithium diisopropylamide / 1) THF, hexane, -78 deg C, 10 min, -25 deg C, 10 min; 2) -23 deg C, 10 min

8: pyridine / CH₂Cl₂ / 4.5 h / Ambient temperature

9: 77 percent / 1,5-diazobicyclo<5.4.0>undec-5-ene / benzene / 0.67 h

10: 67 percent / Dowex 50W-X₈ (H+) / CHCl₃ / 3 h

11: 5.0 mg / pyridine, 4-dimethylaminopyridine / tetrahydrofuran / 43 h

12: 81 percent / Dowex 1-X₈ (OH^(1-)), methanol / 2 h / 0 °C

With pyridine; 1H-imidazole; methanol; dmap; sodium hydroxide; thionyl chloride; Dowex 1-X₈ (OH^(1-)); Dowex 50W-X₈ (H+); 6,6'-di-tert-butyl-4,4'-thiodi-o-cresol; water; lithium carbonate; 3-chloro-benzenecarboperoxoic acid; silver(l) oxide; diborane; 1,5-Diazabicyclo[5.4.0]undec-5-ene; lithium diisopropyl amide; N-bromoacetamide; In tetrahydrofuran; dichloromethane; chloroform; N,N-dimethyl-formamide; benzene;

DOI:10.1021/ja00538a030

upstream raw materials:

(Z)-2-Methyl-but-2-enoic acid (3aR,4S,7aR)-6-formyloxymethyl-5-((S)-4-formyloxy-1-methyl-butyl)-3-methylene-2-oxo-2,3,3a,4,7,7a-hexahydro-benzofuran-4-yl ester

(Z)-2-methyl-2-butenoic anhydride

(3aα,5β,8aα,9aα)-3a,6,7,8a,9,9a-hexahydro-5,8a-dimethylnaphtho<2,3-b>furan-2,8(3H,5H)-dione

(1aS*,2α,5aβ,6aβ,9aβ,9bα)-hexahydro-2,5a-dimethyl-2H-oxireno<4,4a>naphtho<2,3-b>furan-5,8(5aH,9H)-dione