[(2R,3S,4S)-3,4,5-triacetyloxy-6-cyano-3,4-dihydro-2H-pyran-2-yl]methyl acetate

Base Information

• Chemical Name: [(2R,3S,4S)-3,4,5-triacetyloxy-6-cyano-3,4-dihydro-2H-pyran-2-yl]methyl acetate
• CAS No.: 120085-67-8
• Molecular Formula: C₁₅H₁₇NO₉
• Molecular Weight: 355.301
• DSSTox Substance ID: DTXSID001177030
• Mol file: 120085-67-8.mol

Synonyms:120085-67-8;3,4,5,7-Tetra-O-acetyl-2,6-anhydro-D-lyxo-hept-2-enonitrile;[(2R,3S,4S)-3,4,5-triacetyloxy-6-cyano-3,4-dihydro-2H-pyran-2-yl]methyl acetate;BIQBNECJLXVDNJ-VHDGCEQUSA-N;DTXSID001177030;W-200935;D-lyxo-Hept-2-enononitrile, 2,6-anhydro-, 3,4,5,7-tetraacetate

Chemical Property of [(2R,3S,4S)-3,4,5-triacetyloxy-6-cyano-3,4-dihydro-2H-pyran-2-yl]methyl acetate

Chemical Property:

• PSA: 138.22000
• LogP: 0.10998
• XLogP3: -0.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 9
• Exact Mass: 355.09033112
• Heavy Atom Count: 25
• Complexity: 657

Purity/Quality:

98%min ^*data from raw suppliers

3,4,5,7-Tetra-O-acetyl-2,6-anhydro-D-lyxo-hept-2-enononitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCC1C(C(C(=C(O1)C#N)OC(=O)C)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)OC(=O)C

Technology Process of [(2R,3S,4S)-3,4,5-triacetyloxy-6-cyano-3,4-dihydro-2H-pyran-2-yl]methyl acetate

There total 2 articles about [(2R,3S,4S)-3,4,5-triacetyloxy-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: 81.0%

2,3,4,6-tetra-O-acetyl-1-bromo-1-deoxy-β-D-galactopyranosyl cyanide (83497-42-1) → 3,4,5,7-tetra-O-acetyl-2,6-anhydro-D-lyxo-hept-2-enononitrile (120085-67-8)

Guidance literature:

With silver trifluoromethanesulfonate; mercury(II) cyanide; In nitromethane; for 0.0833333h; Heating;

DOI:10.1016/0008-6215(89)85101-8

Reference yield: 20.0%

2,3,4,6-tetra-O-acetyl-1-bromo-1-deoxy-β-D-galactopyranosyl cyanide (83497-42-1) → 3,4,5,7-tetra-O-acetyl-2,6-anhydro-D-lyxo-hept-2-enononitrile (120085-67-8) + 2,3,5,6-tetra-O-acetyl-D-galactono-1,4-lactone (65143-68-2,69881-31-8,79580-58-8,79580-59-9,112241-17-5,136345-67-0,136345-68-1)

Guidance literature:

With mercury(II) cyanide; In dimethyl sulfoxide; at 100 ℃;

DOI:10.1016/0008-6215(91)84157-A

upstream raw materials:

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

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