Phytuberin

Base Information

• Chemical Name: Phytuberin
• CAS No.: 37209-50-0
• Molecular Formula: C₁₇H₂₆O₄
• Molecular Weight: 294.391
• UNII: RR00OUQ5B6
• DSSTox Substance ID: DTXSID10958386
• Nikkaji Number: J18.390C
• Wikidata: Q27107914
• Mol file: 37209-50-0.mol

Synonyms:phytuberin

Chemical Property of Phytuberin

Chemical Property:

• Vapor Pressure: 1.48E-05mmHg at 25°C
• Boiling Point: 366.3°Cat760mmHg
• Flash Point: 157.5°C
• PSA: 44.76000
• Density: 1.11g/cm³
• LogP: 3.20610
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 294.18310931
• Heavy Atom Count: 21
• Complexity: 497

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OC(C)(C)C1CCC2(COC3(C2(C1)OC=C3)C)C
• Isomeric SMILES: CC(=O)OC(C)(C)[C@@H]1CC[C@]2(CO[C@]3([C@]2(C1)OC=C3)C)C

Technology Process of Phytuberin

There total 39 articles about Phytuberin 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: 84.0%

deacetylphytuberin (56857-64-8) + acetic anhydride (108-24-7) → (4R,5R)-1,4:2,5-diepoxy-1,2-secoeudesm-2-en-11-yl acetate (37209-50-0,55304-03-5,39311-20-1)

Guidance literature:

With dmap; triethylamine; for 16h; Ambient temperature;

DOI:10.1246/bcsj.55.1202

Reference yield: 62.0%

(3S,4S,5R)-1,4:2,5-diepoxy-3-phenylselanyl-1,2-secoeudesman-11-yl acetate (548757-12-6) → (4R,5R)-1,4:2,5-diepoxy-1,2-secoeudesm-2-en-11-yl acetate (37209-50-0,55304-03-5,39311-20-1)

Guidance literature:

(3S,4S,5R)-1,4:2,5-diepoxy-3-phenylselanyl-1,2-secoeudesman-11-yl acetate; With ozone; In dichloromethane; at -78 ℃;

With pyridine; In tetrachloromethane; dichloromethane; for 1.5h; Heating;

DOI:10.1021/jo034129d

Reference yield:

(1S,3S,6R)-3-Benzyloxymethyl-3,7,7-trimethyl-bicyclo[4.1.0]heptan-2-one (76207-98-2) → (4R,5R)-1,4:2,5-diepoxy-1,2-secoeudesm-2-en-11-yl acetate (37209-50-0,55304-03-5,39311-20-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 85 percent / p-toluenesulfonic acid

2: 92 percent / tetrahydrofuran / 1 h / -78 °C

3: 60 percent Turnov_. / diethyl ether / 84 h / -24 °C

4: hydrogen / 10percent Pd(C) / aq. ethanol

5: 63 percent / DIBAL-H / 1.) -40 deg C, 1.0 h, 2.) 0 deg C, 0.5 h

6: 71 percent / Et₃N, 4-N,N-dimethylaminopyridine

With dmap; hydrogen; diisobutylaluminium hydride; toluene-4-sulfonic acid; triethylamine; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethanol;

DOI:10.1021/ja00545a032

upstream raw materials:

deacetylphytuberin

acetic anhydride

Acetic acid (3aR,5aS,8R,9aR)-8-(1-acetoxy-1-methyl-ethyl)-3a,5a-dimethyl-octahydro-benzo[c]furo[3,2-b]furan-2-yl ester

(3S,4S,5R)-1,4:2,5-diepoxy-3-phenylselanyl-1,2-secoeudesman-11-yl acetate

Downstream raw materials:

deacetylphytuberin

Refernces

• 1、 Prange, Thierry,Rodriguez, Maria S.,Suarez, Ernesto. "Synthesis of phytuberin. 4-endo-tet acid-catalyzed cyclization of α-hydroxy epoxides". . p. 4422 - 4431. Retrieved 2007/10/03.
• 2、 Findlay, John A.,Desai, Dixit N.,Lonergan, Greg C.,White, Peter S.. "Total synthesis of (-)-phytuberin". . p. 2827 - 2828. Retrieved 2007/10/02.