(3beta,6beta)-Furanoeremophilane-3,6-diol

Base Information

• Chemical Name: (3beta,6beta)-Furanoeremophilane-3,6-diol
• CAS No.: 34335-94-9
• Molecular Formula: C₁₅H₂₂O₃
• Molecular Weight: 250.338
• Wikidata: Q110077533
• Mol file: 34335-94-9.mol

Synonyms:(3beta,6beta)-Furanoeremophilane-3,6-diol;Furanofukinol;CHEBI:174298;3,4a,5-trimethyl-5,6,7,8,8a,9-hexahydro-4H-benzo[][1]benzouran-4,6-diol

Chemical Property of (3beta,6beta)-Furanoeremophilane-3,6-diol

Chemical Property:

• PSA: 53.60000
• LogP: 2.59080
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 250.15689456
• Heavy Atom Count: 18
• Complexity: 332

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1C(CCC2C1(C(C3=C(C2)OC=C3C)O)C)O

Technology Process of (3beta,6beta)-Furanoeremophilane-3,6-diol

There total 2 articles about (3beta,6beta)-Furanoeremophilane-3,6-diol 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:

6-O-Angeloylfuranokinol (54911-14-7) → Furanofukinol (34335-94-9)

Guidance literature:

With potassium tert-butylate; In dimethyl sulfoxide; for 12h; Ambient temperature;

DOI:10.1246/bcsj.64.1071

Reference yield:

3β,6β-diangeloyloxy-10β-H-furanoeremophilane → Furanofukinol (34335-94-9)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; for 0.5h; Heating;

DOI:10.1016/0031-9422(80)85061-8

Reference yield:

Furanofukinol (34335-94-9) → Toluene-4-sulfonic acid (4aS,5R,6S,8aR,9aR)-3,4a,5-trimethyl-2-oxo-2,4,4a,5,6,7,8,8a,9,9a-decahydro-naphtho[2,3-b]furan-6-yl ester (135305-70-3)

Guidance literature:

Multi-step reaction with 5 steps

2: 1.) 1 M NaOMe-MeOH / 1.) MeOH, 2.) reflux, 9 h

3: 93 percent / p-toluenesulfonic acid / CH₂Cl₂ / 18 h

4: 66 percent / NaBH₄ / methanol / 2 h

5: 84.4 percent / pyridine / 24 h / Ambient temperature

With pyridine; methanol; sodium tetrahydroborate; sodium methylate; toluene-4-sulfonic acid; In methanol; dichloromethane;

DOI:10.1246/bcsj.64.1071

upstream raw materials:

6-O-Angeloylfuranokinol

Downstream raw materials:

Eremophilenolid

Toluene-4-sulfonic acid (4aS,5R,6S,8aR,9aR)-3,4a,5-trimethyl-2-oxo-2,4,4a,5,6,7,8,8a,9,9a-decahydro-naphtho[2,3-b]furan-6-yl ester