Goniodiol 7-acetate

Base Information

• Chemical Name: Goniodiol 7-acetate
• CAS No.: 96422-53-6
• Deprecated CAS: 139067-63-3
• Molecular Formula: C₁₅H₁₆O₅
• Molecular Weight: 276.289
• Hs Code.: 2932999099
• DSSTox Substance ID: DTXSID30914520
• Nikkaji Number: J1.899.136E
• Wikidata: Q72480809
• Metabolomics Workbench ID: 135322
• ChEMBL ID: CHEMBL454527
• Mol file: 96422-53-6.mol

Synonyms:(7,8-dihydro-7-acetoxy-8-hydroxystyryl)-5,6-dihydro-2-pyrone;goniodiol-7-monoacetate

Chemical Property of Goniodiol 7-acetate

Chemical Property:

• Boiling Point: 396.7°Cat760mmHg
• Flash Point: 144.4°C
• PSA: 72.83000
• Density: 1.265g/cm³
• LogP: 1.52340
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 276.09977361
• Heavy Atom Count: 20
• Complexity: 384

Purity/Quality:

98%Min ^*data from raw suppliers

Goniodiol7-acetate ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OC(C1CC=CC(=O)O1)C(C2=CC=CC=C2)O
• Isomeric SMILES: CC(=O)O[C@@H]([C@H]1CC=CC(=O)O1)[C@@H](C2=CC=CC=C2)O

Technology Process of Goniodiol 7-acetate

There total 16 articles about Goniodiol 7-acetate 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:

acetic acid 2-(tert-butyl-dimethyl-silanyloxy)-1-(6-oxo-3,6-dihydro-2H-pyran-2-yl)-2-phenyl-ethyl ester → (6R,7R,8R)-goniodiol-7-monoacetate (96422-53-6)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃;

DOI:10.1055/s-2002-32977

Reference yield:

(1R,2R)-1-phenyl-but-3-ene-1,2-diol (145376-17-6) → (6R,7R,8R)-goniodiol-7-monoacetate (96422-53-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 98 percent / Et₃N / CH₂Cl₂ / 2 h / 0 °C

2: 71 percent / PdCl₂(CH₃CN)2 / dimethylformamide; H₂O / 1 h / 0 °C

3: 96 percent / Et₃N / dimethylformamide / 6 h / 20 °C

4: 90 percent / AD-mix-β / 16 h / 0 °C

5: 81 percent / PTS / toluene / 80 °C

6: Et₃N; DMAP / 1 h / 0 °C

7: TBAF / tetrahydrofuran / 20 °C

With dmap; AD-mix-β; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; triethylamine; dichloro bis(acetonitrile) palladium(II); In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; toluene; 4: Sharpless dihydroxylation;

DOI:10.1055/s-2002-32977

Reference yield:

(4R,5R)-4-Phenyl-5-vinyl-[1,3]dioxolan-2-one (474087-63-3) → (6R,7R,8R)-goniodiol-7-monoacetate (96422-53-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 71 percent / PdCl₂(CH₃CN)2 / dimethylformamide; H₂O / 1 h / 0 °C

2: 96 percent / Et₃N / dimethylformamide / 6 h / 20 °C

3: 90 percent / AD-mix-β / 16 h / 0 °C

4: 81 percent / PTS / toluene / 80 °C

5: Et₃N; DMAP / 1 h / 0 °C

6: TBAF / tetrahydrofuran / 20 °C

With dmap; AD-mix-β; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; triethylamine; dichloro bis(acetonitrile) palladium(II); In tetrahydrofuran; water; N,N-dimethyl-formamide; toluene; 3: Sharpless dihydroxylation;

DOI:10.1055/s-2002-32977

upstream raw materials:

acetic anhydride

(6S,7S,8S)-(-)-goniodiol

goniodiol diacetate

(1R,2R)-1-phenyl-but-3-ene-1,2-diol

Downstream raw materials:

goniodiol diacetate

goniotriol triacetate

7,8-di-O-acetyl-goniodiol

Refernces

• 1、 Surivet, Jean-Philippe,Gore, Jacques,Vatele, Jean-Michel. "Enantioselective synthesis of (+)-goniodiol and of its naturally occurring acetylated analogs". . p. 14877 - 14890. Retrieved 2007/10/03.