6-(1,2-Epoxypropyl)-5,6-dihydro-5-hydroxy-2H-pyran-2-one acetate

Base Information

• Chemical Name: 6-(1,2-Epoxypropyl)-5,6-dihydro-5-hydroxy-2H-pyran-2-one acetate
• CAS No.: 30387-51-0
• Molecular Formula: C₁₀H₁₂O₅
• Molecular Weight: 212.202
• Hs Code.: 2932999099
• UNII: 8KOW0SA4L3
• DSSTox Substance ID: DTXSID501037425
• Nikkaji Number: J647.238I
• Wikidata: Q27270679
• NCI Thesaurus Code: C90674
• Metabolomics Workbench ID: 114730
• Mol file: 30387-51-0.mol

Synonyms:asperlin

Chemical Property of 6-(1,2-Epoxypropyl)-5,6-dihydro-5-hydroxy-2H-pyran-2-one acetate

Chemical Property:

• Vapor Pressure: 2.23E-05mmHg at 25°C
• Boiling Point: 360.4°Cat760mmHg
• Flash Point: 162.3°C
• PSA: 65.13000
• Density: 1.28g/cm³
• LogP: 0.18700
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 212.06847348
• Heavy Atom Count: 15
• Complexity: 322

Purity/Quality:

95%+ ^*data from raw suppliers

ASPERLIN 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(O1)C2C(C=CC(=O)O2)OC(=O)C
• Isomeric SMILES: C[C@@H]1[C@H](O1)[C@H]2[C@H](C=CC(=O)O2)OC(=O)C
• Uses: Antibacterial; antineoplastic.

Technology Process of 6-(1,2-Epoxypropyl)-5,6-dihydro-5-hydroxy-2H-pyran-2-one acetate

There total 62 articles about 6-(1,2-Epoxypropyl)-5,6-dihydro-5-hydroxy-2H-pyran-2-one 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: 91.0%

Acetic acid (2R,3S,6R)-6-hydroxy-2-((2S,3R)-3-methyl-oxiranyl)-3,6-dihydro-2H-pyran-3-yl ester → (+)-asperlin (30387-51-0)

Guidance literature:

With Celite; sodium acetate; pyridinium chlorochromate; In dichloromethane;

DOI:10.3987/COM-94-7001

Reference yield: 91.0%

(2S,3S)-3-acetoxy-2-<(1S,2R)-1',2'-epoxypropyl>-2,6-dihydropyran-6-ol (220278-22-8) → (+)-asperlin (30387-51-0)

Guidance literature:

With Celite; sodium acetate; pyridinium chlorochromate; In dichloromethane; for 1h; Ambient temperature;

DOI:10.3987/com-98-s(h)5

Reference yield: 73.0%

(+)-Acetylphomalactone (23791-20-0) → (+)-asperlin (30387-51-0)

Guidance literature:

With dihydrogen peroxide; trifluoroacetic acid; In dichloromethane; at 0 ℃;

DOI:10.1016/S0040-4039(98)02675-6

upstream raw materials:

acetic acid

(5R,6R,1'S,2'R)-5,6-dihydro-5-hydroxy-6-(1',2'-epoxypropyl)-2H-pyran-2-one

(+)-Acetylphomalactone

acetic anhydride

Refernces

• 1、 Schlessinger, Richard H.,Gillman, Kevin W.. "Asymmetric total synthesis of (+)-phomalactone, (+)-acetylphomalactone and (+)-asperlin utilizing a novel syn-selective C4-oxa-vinylogous urethane". . p. 1257 - 1260. Retrieved 2007/10/03.
• 2、 Yang, Zhi-Cai,Jiang, Xiao-Bin,Wang, Zhi-Min,Zhou, Wei-Shan. "Total syntheses of (+)-asperlin, (+)-acetylphomalactone and (5S,6S,7R,8S)-asperlin based on the kinetic resolution of 2-furylmethanols". . p. 317 - 321. Retrieved 2007/10/03.