[(2R,3S,4R)-3,4-diacetyloxy-6-cyano-3,4-dihydro-2H-pyran-2-yl]methyl acetate

Base Information

• Chemical Name: [(2R,3S,4R)-3,4-diacetyloxy-6-cyano-3,4-dihydro-2H-pyran-2-yl]methyl acetate
• CAS No.: 120085-62-3
• Molecular Formula: C₁₃H₁₅NO₇
• Molecular Weight: 297.265
• DSSTox Substance ID: DTXSID20370474
• Wikidata: Q82157631
• Mol file: 120085-62-3.mol

Synonyms:120085-62-3;4,5,7-TRI-O-ACETYL-2,6-ANHYDRO-3-DEOXY-D-LYXO-HEPT-2-ENONONITRILE;120085-63-4;[(2R,3S,4R)-3,4-diacetyloxy-6-cyano-3,4-dihydro-2H-pyran-2-yl]methyl acetate;[(2R,3S,4R)-3,4-BIS(ACETYLOXY)-6-CYANO-3,4-DIHYDRO-2H-PYRAN-2-YL]METHYL ACETATE;4,5,7-TRI-O-ACETYL-2,6-ANHYDRO-3-DEOXY-D-ARABINO-HEPT-2-ENONONITRILE,;ST50307549;DTXSID20370474;W-200933;4,5,7,-Tri-o-acetyl-2,6-anhyro-3-deoxy-D-lyxo-hept-2-enononitrile;(2R,3S,4R)-2-(acetoxymethyl)-6-cyano-3,4-dihydro-2H-pyran-3,4-diyl diacetate

Chemical Property of [(2R,3S,4R)-3,4-diacetyloxy-6-cyano-3,4-dihydro-2H-pyran-2-yl]methyl acetate

Chemical Property:

• Vapor Pressure: 1.54E-06mmHg at 25°C
• Boiling Point: 397.8°Cat760mmHg
• Flash Point: 174°C
• PSA: 111.92000
• Density: 1.29g/cm³
• LogP: 0.21918
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 7
• Exact Mass: 297.08485182
• Heavy Atom Count: 21
• Complexity: 516

Purity/Quality:

4,5,7-TRI-O-ACETYL-2,6-ANHYDRO-3-DEOXY-D-ARABINO-HEPT-2-ENONONITRILE 95.00% ^*data from reagent suppliers

Safty Information:

• Safety Statements: S24/25:Avoid contact with skin and eyes.

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCC1C(C(C=C(O1)C#N)OC(=O)C)OC(=O)C
• Isomeric SMILES: CC(=O)OC[C@@H]1[C@H]([C@@H](C=C(O1)C#N)OC(=O)C)OC(=O)C

Technology Process of [(2R,3S,4R)-3,4-diacetyloxy-6-cyano-3,4-dihydro-2H-pyran-2-yl]methyl acetate

There total 10 articles about [(2R,3S,4R)-3,4-diacetyloxy-6-cyano-3,4-dihydro-2H-pyran-2-yl]methyl 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: 70.0%

3,4,5,7-tetra-O-acetyl-2,6-anhydro-D-glycero-D-gulo-heptononitrile (52443-05-7) → 4,5,7-Tri-O-acetyl-2,6-anhydro-3-deoxy-2,3-didehydro-D-arabino-heptononitrile (120085-62-3)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; -20 deg C, 5 h; -5 deg C, overnight;

DOI:10.1016/S0008-6215(96)00227-3

Reference yield: 62.0%

2,3,4,6-tetra-O-acetyl-1-deoxy-1-bromo-β-D-glycopyranosyl cyanide (82469-74-7) → 4,5,7-Tri-O-acetyl-2,6-anhydro-3-deoxy-2,3-didehydro-D-arabino-heptononitrile (120085-62-3)

Guidance literature:

With pyridine; zinc; In benzene; Heating;

Reference yield: 60.0%

3,4,5,7-tetra-O-acetyl-2,6-anhydro-D-glycero-D-galacto-heptononitrile (86651-66-3) → 4,5,7-Tri-O-acetyl-2,6-anhydro-3-deoxy-2,3-didehydro-D-arabino-heptononitrile (120085-62-3)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; for 24h; Ambient temperature;

upstream raw materials:

(1R,2R)-trans-1,2-cyclohexanediol

4,5,7-tri-O-acetyl-2,6-anhydro-2-bromo-3-deoxy-D-gluco-heptononitrile

2,3,4,6-tetra-O-acetyl-1-deoxy-1-bromo-β-D-glycopyranosyl cyanide

3,4,5,7-tetra-O-acetyl-2,6-anhydro-D-glycero-D-galacto-heptononitrile

Downstream raw materials:

5-(3,4-Di-O-acetyl-2-deoxy-6-O-diphenoxyphosphinoyl-β-D-arabino-hexopyranosyl)tetrazole