Goniodiol 8-acetate

Base Information

• Chemical Name: Goniodiol 8-acetate
• CAS No.: 144429-71-0
• Molecular Formula: C15H16O5
• Molecular Weight: 276.289
• Mol file: 144429-71-0.mol

Synonyms:Goniodiol 8-acetate

Chemical Property of Goniodiol 8-acetate

Chemical Property:

• Boiling Point: 412.4±15.0 °C(Predicted)
• PKA: 12.69±0.20(Predicted)
• PSA: 72.83000
• Density: 1.265±0.06 g/cm3(Predicted)
• LogP: 1.52340

Purity/Quality:

98% ^*data from raw suppliers

Goniodiol8-acetate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Goniodiol 8-acetate

There total 27 articles about Goniodiol 8-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: 72.0%

(Z)-(5R,6S,7R)-7-Acetoxy-5,6-dihydroxy-7-phenyl-hept-2-enoic acid methyl ester (473980-92-6) → (6R,7R,8R)-goniodiol-8-monoacetate (144429-71-0)

Guidance literature:

With pyridinium p-toluenesulfonate; In toluene; at 80 ℃;

DOI:10.1055/s-2002-32977

Reference yield:

(2E)-3-phenyl-2-propen-1-ol (4407-36-7) → (6R,7R,8R)-goniodiol-8-monoacetate (144429-71-0)

Guidance literature:

Multi-step reaction with 14 steps

1: 86 percent / TBHP, Ti(OiPr)4, L-(+)-diisopropyl tartrate, molecular sieves 4 Angstroem / CH₂Cl₂ / -20 °C

2: 90 percent / CHCl₃ / -20 - 0 °C

3: imidazole / tetrahydrofuran / Ambient temperature

4: 15percent aq. NaOH / tetrahydrofuran / Ambient temperature

5: p-TsOH / CH₂Cl₂ / Ambient temperature

6: nBu₄NF / tetrahydrofuran / 0 °C

7: Me₂SO, (COCl)2, Et₃N / CH₂Cl₂ / -78 - -20 °C

8: tetrahydrofuran / -78 - -30 °C

9: 84 percent / TBHP, VO(acac)2 / CH₂Cl₂ / 0 °C

10: 1) CrO₃, 2) NaBH(OAc)3 / 1) HOAc, 25 deg C to 30 deg C, 15 min, 2) iPrOH, HOAc, -10 deg C to r.t.

11: 98 percent / pyridine, DMAP / CH₂Cl₂ / 4 h / Ambient temperature

12: 87 percent / Zn-Hg, HCl / diethyl ether / 4 h / Ambient temperature

13: 85 percent / DBU / benzene / 2 h / 80 °C

14: 1) TFA, 2) DMAP, pyridine / 1) H₂O, r.t., 4 h, 2) CH₂Cl₂, 0 deg C to r.t.

With pyridine; 1H-imidazole; chromium(VI) oxide; titanium(IV) isopropylate; hydrogenchloride; tert.-butylhydroperoxide; dmap; sodium hydroxide; oxalyl dichloride; bis(acetylacetonate)oxovanadium; L-(+)-diisopropyl tartrate; 4 A molecular sieve; tetrabutyl ammonium fluoride; sodium tris(acetoxy)borohydride; toluene-4-sulfonic acid; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; mercury; trifluoroacetic acid; zinc; In tetrahydrofuran; diethyl ether; dichloromethane; chloroform; benzene;

DOI:10.1039/c39950000743

Reference yield:

(1R,2R)-1-phenyl-but-3-ene-1,2-diol (145376-17-6) → (6R,7R,8R)-goniodiol-8-monoacetate (144429-71-0)

Guidance literature:

Multi-step reaction with 5 steps

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

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

3: 91 percent / Et₃N; DMAP / 1 h / 0 °C

4: 87 percent / AD-mix-β / 16 h / 0 °C

5: 72 percent / PTS / toluene / 80 °C

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

DOI:10.1055/s-2002-32977

upstream raw materials:

acetic anhydride

(6R,4'S,5'R)-6-(2',2'-dimethyl-5'-phenyl-[1',3']dioxolan-4'-yl)-5,6-dihydropyran-2-one

(Z)-(5R,6S,7R)-7-Acetoxy-5,6-dihydroxy-7-phenyl-hept-2-enoic acid methyl ester

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

Downstream raw materials:

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.