(S)-Patulin Methyl Ether

Base Information

• Chemical Name: (S)-Patulin Methyl Ether
• CAS No.: 123251-09-2
• Molecular Formula: C₈H₈O₄
• Molecular Weight: 168.149
• DSSTox Substance ID: DTXSID60559302
• Metabolomics Workbench ID: 163433
• Wikidata: Q82441976
• Mol file: 123251-09-2.mol

Synonyms:(S)-Patulin Methyl Ether;123251-09-2;(S)-O-Methyl Patulin;(S)-4-Methoxy-4H-furo[3,2-c]pyran-2(6H)-one;(4S)-4-methoxy-4,6-dihydrofuro[3,2-c]pyran-2-one;Aspergilsmin C;(4S)-4-methoxy-2H,4H,6H-furo[3,2-c]pyran-2-one;DTXSID60559302;CHEBI:210120;4-methoxy-4,6-dihydrouro[3,2-c]pyran-2-one;A905713;(4S)-4-Methoxy-4H-furo[3,2-c]pyran-2(6H)-one;J-004902

Chemical Property of (S)-Patulin Methyl Ether

Chemical Property:

• PSA: 44.76000
• LogP: 0.35620
• XLogP3: -0.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 168.04225873
• Heavy Atom Count: 12
• Complexity: 277

Purity/Quality:

97% ^*data from raw suppliers

(S)-PatulinMethylEther ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1C2=CC(=O)OC2=CCO1
• Isomeric SMILES: CO[C@@H]1C2=CC(=O)OC2=CCO1
• Uses: Protected Patulin.

Technology Process of (S)-Patulin Methyl Ether

There total 11 articles about (S)-Patulin Methyl Ether 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: 80.0%

(4S,7S,7aR)-7-hydroxy-4-methoxy-7,7a-dihydrofuro<3,2-c>pyran-2(4H,6H)-one (123251-08-1) → (S)-O-methylpatulin (123251-09-2)

Guidance literature:

With methanesulfonyl chloride; In pyridine; for 24h;

Reference yield: 41.0%

(Z)-2-methoxy-3-methoxycarbonylmethylene-2,3,5,6-tetrahydro-4-pyranone (162337-84-0) → methylpatulin (123251-09-2)

Guidance literature:

With calcium hydroxide; In benzene; for 0.5h; Heating;

DOI:10.1248/cpb.42.2167

Reference yield:

3-oxopentanedioic acid dimethyl ester (1830-54-2) → methylpatulin (123251-09-2)

Guidance literature:

Multi-step reaction with 7 steps

1: 78 percent / pyridine / H₂O / 24 h / 50 °C

2: 80 percent / LiAlH₄ / diethyl ether / 3 h

3: 68 percent / MnO₂ / CH₂Cl₂ / 1.5 h

4: 91 percent / pyridinium p-toluenesulfonate / benzene / 1.5 h / Heating

5: m-chloroperbenzoic acid, citrate buffer pH 8 / CH₂Cl₂ / 2 h

6: methanol; diethyl ether

7: 41 percent / Ca(OH)2 / benzene / 0.5 h / Heating

With pyridine; manganese(IV) oxide; calcium hydroxide; lithium aluminium tetrahydride; citrate buffer pH 8; pyridinium p-toluenesulfonate; 3-chloro-benzenecarboperoxoic acid; In methanol; diethyl ether; dichloromethane; water; benzene;

DOI:10.1248/cpb.42.2167

upstream raw materials:

patulin

methyl iodide

(Z)-2-methoxy-3-methoxycarbonylmethylene-2,3,5,6-tetrahydro-4-pyranone

2-(2-hydroxy-ethyliden)-5-oxo-2,5-dihydro-furan-3-carbaldehyde