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

Base Information

• Chemical Name: (6S,7S,8S)-(-)-goniodiol
• CAS No.: 936210-36-5
• Molecular Formula: C₁₃H₁₄O₄
• Molecular Weight: 234.252
• Mol file: 936210-36-5.mol

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

Chemical Property of (6S,7S,8S)-(-)-goniodiol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (6S,7S,8S)-(-)-goniodiol

There total 23 articles about (6S,7S,8S)-(-)-goniodiol 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: 96.0%

(S)-6-((2R,3R)-3-phenyloxiran-2-yl)-5,6-dihydro-2H-pyran-2-one (110044-45-6) → (6S,7S,8S)-(-)-goniodiol (936210-36-5)

Guidance literature:

With water; at 60 ℃; for 24h; Temperature; Reagent/catalyst; stereoselective reaction;

DOI:10.1021/acs.jnatprod.6b00386

Reference yield: 35.0%

(S)-6-((2R,3R)-3-phenyloxiran-2-yl)-5,6-dihydro-2H-pyran-2-one (110044-45-6) → (1S,5S,7R,8R)-3-endo,7-endo-(?)-9-deoxygoniopypyrone + (S)-goniothalamin (122046-62-2) + (6S,7S,8S)-(-)-goniodiol (936210-36-5)

Guidance literature:

(S)-6-((2R,3R)-3-phenyloxiran-2-yl)-5,6-dihydro-2H-pyran-2-one; With water; silver trifluoromethanesulfonate; at 20 ℃; for 3h;

With sodium hydrogencarbonate; In water; stereoselective reaction;

DOI:10.1021/acs.jnatprod.6b00386

Reference yield:

(2E)-3-phenyl-2-propen-1-ol (4407-36-7) → (6S,7S,8S)-(-)-goniodiol (936210-36-5)

Guidance literature:

Multi-step reaction with 5 steps

1: LiBEt₃H / tetrahydrofuran / 1 h / -78 °C

2: ethyldiisopropylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 5 h / 0 °C

3: benzylidene-bis(tricyclohexylphosphine)dichlororuthenium / CH₂Cl₂ / 20 °C

4: FeCl₃ / CHCl₃

With dmap; iron(III) chloride; lithium triethylborohydride; N-ethyl-N,N-diisopropylamine; Grubbs catalyst first generation; In tetrahydrofuran; dichloromethane; chloroform;

DOI:10.1246/bcsj.80.387

upstream raw materials:

goniodiol diacetate

(6S)-6-[(4R,5S)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]-5,6-dihydro-2H-pyran-2-one

(1S)-1-[(4R,5S)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]but-3-enyl acrylate

(2E)-3-phenyl-2-propen-1-ol

Downstream raw materials:

goniotriol triacetate

goniodiol diacetate

goniodiol monoacetate