(-)-Colletol

Base Information

• Chemical Name: (-)-Colletol
• CAS No.: 50376-40-4
• Molecular Formula: C₁₄H₂₀O₅
• Molecular Weight: 268.31
• Mol file: 50376-40-4.mol

Synonyms:1,7-Dioxacyclotetradeca-3,9-diene-2,8-dione,12-hydroxy-6,14-dimethyl-, [6R-(3E,6R*,9E,12S*,14R*)]-; (-)-Colletol; Colletol

Chemical Property of (-)-Colletol

Chemical Property:

• PSA: 72.83000
• LogP: 1.50700

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (-)-Colletol

There total 63 articles about (-)-Colletol 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: 81.0%

(+)-(6R,14R,12S,3E,9E)-6,14-dimethyl-12-(tert-butyldiphenylsilyloxy)-1,7-dioxacyclotetradeca-3,9-diene-2,8-dione → (-)-colletol (50376-40-4)

Guidance literature:

With tetrabutyl ammonium fluoride; benzoic acid; In tetrahydrofuran; at 20 ℃; for 72h;

DOI:10.1002/(SICI)1099-0690(200001)2000:2<357::AID-EJOC357>3.0.CO;2-N

Reference yield: 79.0%

(3E,6R,9E,12S,14R)-12-(methoxymethoxy)-6,14-dimethyl-1,7-dioxacyclotetradeca-3,9-diene-2,8-dione (231297-92-0) → (-)-colletol (50376-40-4)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; at 25 ℃;

DOI:10.1016/j.tetlet.2005.11.161

Reference yield:

(7R)-7-hydroxy-octa-2,4-dienoic acid methyl ester → (-)-colletol (50376-40-4)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 97 percent / Et₃N; DMAP / CH₂Cl₂ / 48 h

2.1: 71 percent / CH₃SO₂NH₂; K₂CO₃; K₃Fe(CN)6 / OsO₄; (DHQD)2PHAL / 2-methyl-propan-2-ol; H₂O / 0 °C

3.1: PPTS / methanol / 24 h

3.2: 88 percent / p-TsOH / methanol / 12 h

4.1: Et₃N; trichlorobenzoyl chloride / tetrahydrofuran / 3 h

4.2: 77 percent / DMAP / toluene / 2 h / 90 °C

5.1: 79 percent / TBAF; benzoic acid / tetrahydrofuran / 48 h

6.1: 79 percent / LiOH / tetrahydrofuran; H₂O / 6 h

7.1: 72 percent / DCC; DMAP; DMAP*HCl / CH₂Cl₂ / 12 h

8.1: 86 percent / Dowex 50W-8H⁽¹⁺⁾ resin / methanol / 6 h / Heating

9.1: 90 percent / pyridine / CH₂Cl₂ / 1 h

10.1: HCO₂H; Et₃N; Pd₂(dba)3*CHCl₃ / tetrahydrofuran / 2 h / Heating

With pyridine; dmap; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; lithium hydroxide; formic acid; methanesulfonamide; Dowex 50W-8H⁽¹⁺⁾ resin; trichlorobenzoyl chloride; tetrabutyl ammonium fluoride; 4-(dimethylamino)pyridine hydrochloride; pyridinium p-toluenesulfonate; potassium carbonate; triethylamine; dicyclohexyl-carbodiimide; benzoic acid; potassium hexacyanoferrate(III); osmium(VIII) oxide; 1,4-bis(9-O-dihydroquinidine)phthalazine; In tetrahydrofuran; methanol; dichloromethane; water; tert-butyl alcohol; 2.1: Sharpless asymmetric dihydroxylation;

DOI:10.1021/ol0269502

upstream raw materials:

(3E,6R,9E,12S,14R)-12-(methoxymethoxy)-6,14-dimethyl-1,7-dioxacyclotetradeca-3,9-diene-2,8-dione

(8E,14E)-(3aR,5R,11R,15aR)-5,11-Dimethyl-3a,4,5,10,11,15a-hexahydro-1,3,6,12-tetraoxa-cyclopentacyclotetradecene-2,7,13-trione

tert-Butyl-((1R,3S)-3-methoxymethoxy-1-methyl-hex-5-enyloxy)-dimethyl-silane

(E)-(5S,7R)-7-Hydroxy-5-methoxymethoxy-oct-2-enoic acid (R)-1-methyl-but-3-enyl ester