2,3,4-Tri-O-acetyl-1-azido-1-deoxy-b-D-arabinopyranosyl cyanide

Base Information

• Chemical Name: 2,3,4-Tri-O-acetyl-1-azido-1-deoxy-b-D-arabinopyranosyl cyanide
• CAS No.: 168567-91-7
• Molecular Formula: C₁₂H₁₄N₄O₇
• Molecular Weight: 326.266
• DSSTox Substance ID: DTXSID50451063
• Nikkaji Number: J1.276.349B
• Mol file: 168567-91-7.mol

Synonyms:168567-91-7;2,3,4-Tri-O-acetyl-1-azido-1-deoxy-b-D-arabinopyranosyl cyanide;[(3R,4R,5S,6S)-4,5-diacetyloxy-6-azido-6-cyanooxan-3-yl] acetate;2,3,4-TRI-O-ACETYL-1-AZIDO-1-DEOXY-beta-D-ARABINOPYRANOSYL CYANIDE;alpha-D-arabino-2-Hexulopyranosononitrile, 2-azido-2-deoxy-, 3,4,5-triacetate (9CI);DTXSID50451063;MNQOBHCPCLXJGP-WYUUTHIRSA-N;AKOS025294694;2-O,3-O,4-O-Triacetyl-1-azido-beta-D-arabinopyranosyl cyanide

Chemical Property of 2,3,4-Tri-O-acetyl-1-azido-1-deoxy-b-D-arabinopyranosyl cyanide

Chemical Property:

• XLogP3: 0.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 7
• Exact Mass: 326.08624880
• Heavy Atom Count: 23
• Complexity: 606

Purity/Quality:

95% ^*data from raw suppliers

2,3,4-Tri-O-acetyl-1-azido-1-deoxy-b-D-arabinopyranosyl cyanide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(=O)OC1COC(C(C1OC(=O)C)OC(=O)C)(C#N)N=[N+]=[N-]
• Isomeric SMILES: CC(=O)O[C@@H]1CO[C@]([C@H]([C@@H]1OC(=O)C)OC(=O)C)(C#N)N=[N+]=[N-]

Technology Process of 2,3,4-Tri-O-acetyl-1-azido-1-deoxy-b-D-arabinopyranosyl cyanide

There total 3 articles about 2,3,4-Tri-O-acetyl-1-azido-1-deoxy-b-D-arabinopyranosyl cyanide 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%

2,3,4-tri-O-acetyl-1-deoxy-1-bromo-α-D-arabinopyranosyl cyanide (89158-09-8) → 2,3,4-tri-O-acetyl-1-cyano-α-D-arabinopyranosyl azide (168567-91-7)

Guidance literature:

With sodium azide; In dimethyl sulfoxide; for 0.0833333h; Ambient temperature;

DOI:10.1016/0040-4020(96)00440-1

Reference yield:

2,3,4-tri-O-acetyl-1-deoxy-1-bromo-β-D-xylopyranosyl cyanide (83497-43-2) → (1R)-2,3,4-tri-O-acetyl-1-azido-D-xylopyranosyl cyanide (168567-91-7) + (1S)-2,3,4-tri-O-acetyl-1-azido-D-xylopyranosyl cyanide (168567-91-7)

Guidance literature:

With sodium azide; In dimethyl sulfoxide; for 0.0833333h; Yield given. Yields of byproduct given; Ambient temperature;

DOI:10.1016/0040-4020(96)00440-1

Reference yield:

2,3,4-tri-O-acetyl-1-deoxy-1-bromo-β-D-xylopyranosyl cyanide (83497-43-2) → (1R)-2,3,4-tri-O-acetyl-1-azido-D-xylopyranosyl cyanide (168567-91-7) + (1S)-2,3,4-tri-O-acetyl-1-azido-D-xylopyranosyl cyanide (168567-91-7)

Guidance literature:

With sodium azide; In dimethyl sulfoxide; for 0.0833333h; Yield given. Yields of byproduct given; Ambient temperature;

DOI:10.1016/0040-4020(96)00440-1

upstream raw materials:

2,3,4-tri-O-acetyl-1-deoxy-1-bromo-α-D-arabinopyranosyl cyanide

2,3,4-tri-O-acetyl-1-deoxy-1-bromo-β-D-xylopyranosyl cyanide

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