(4-acetyloxy-3,4-dihydro-2H-pyran-3-yl) acetate

Base Information

• Chemical Name: (4-acetyloxy-3,4-dihydro-2H-pyran-3-yl) acetate
• CAS No.: 3945-18-4
• Molecular Formula: C9H12 O5
• Molecular Weight: 200.191
• Hs Code.: 29400000
• European Community (EC) Number: 609-685-6
• Nikkaji Number: J649.999F
• Mol file: 3945-18-4.mol

Synonyms:SCHEMBL14356318;OWKCFBYWQGPLSJ-UHFFFAOYSA-N;3945-18-4;FT-0666326

Chemical Property of (4-acetyloxy-3,4-dihydro-2H-pyran-3-yl) acetate

Chemical Property:

• Appearance/Colour: Clear colorless to yellow oil
• Vapor Pressure: 0.00878mmHg at 25°C
• Refractive Index: 1.458-1.46
• Boiling Point: 266.2 °C at 760 mmHg
• Flash Point: 112.8 °C
• PSA: 61.83000
• Density: 1.2 g/cm³
• LogP: 0.39370
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 200.06847348
• Heavy Atom Count: 14
• Complexity: 258

Purity/Quality:

98%Min ^*data from raw suppliers

3,4-Di-O-acetyl-L-arabinal ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OC1COC=CC1OC(=O)C

Technology Process of (4-acetyloxy-3,4-dihydro-2H-pyran-3-yl) acetate

There total 29 articles about (4-acetyloxy-3,4-dihydro-2H-pyran-3-yl) 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: 95.0%

(2R,3S,4R,5R)-2-bromotetrahydro-2H-pyran-3,4,5-triyl triacetate (39524-37-3) → 3,4-di-O-acetyl-D-arabinal (3152-43-0,3945-17-3,3945-18-4,86257-92-3,89921-34-6,89921-35-7,101052-70-4)

Guidance literature:

With β‐cyclodextrin; zinc; In water; at 20 ℃; for 0.5h; Sonication;

DOI:10.1002/cjoc.201180263

Reference yield: 91.0%

α-1-bromo-1-deoxy-2,3,4-tri-O-acetyl-L-arabinopyranose (75247-31-3) → 3,4-di-O-acetyl-L-arabinal (3945-18-4)

Guidance literature:

With ammonium chloride; zinc; bis(acetylacetonate)oxovanadium; In methanol; at 20 ℃; for 0.166667h; Product distribution / selectivity;

Reference yield: 90.1%

2,3,5-tri-O-acetyl-D-ribopyranosyl bromide (50730-32-0) → 3,4-di-O-acetyl-D-arabinal (3152-43-0,3945-17-3,3945-18-4,86257-92-3,89921-34-6,89921-35-7,101052-70-4)

Guidance literature:

With silver-graphite; zinc; In tetrahydrofuran; at -20 - 25 ℃; for 0.333333h;

DOI:10.1039/c39860001149

upstream raw materials:

2,3,4-tri-O-acetyl-β-D-arabinosyl bromide

acetic anhydride

2,3,4-Tri-O-acetyl-α-D-arabino-pyranosyl chloride

2,3,5-tri-O-acetyl-D-ribopyranosyl bromide

Downstream raw materials:

levulinic acid

Acetic acid (3R,6R)-6-(2-benzyloxymethyl-allyl)-3,6-dihydro-2H-pyran-3-yl ester

Refernces

• 1、 Nemcsok, Tamás,Rapi, Zsolt,Bagi, Péter,Keglevich, Gy?rgy,Bakó, Péter. "Synthesis of xylal- and arabinal-based crown ethers and their application as asymmetric phase transfer catalysts". . p. 107 - 119. Retrieved 2019/11/16.
• 2、 -. "THERAPEUTIC COMPOUNDS". Page/Page column 21. . Retrieved 2017/06/30.