(E)-5,6,7,9-tetra-O-acetyl-4,8-anhydro-2,3-dideoxy-D-arabino-non-4-enononitrile

Base Information

• Chemical Name: (E)-5,6,7,9-tetra-O-acetyl-4,8-anhydro-2,3-dideoxy-D-arabino-non-4-enononitrile
• CAS No.: 144427-71-4
• Molecular Formula: C₁₇H₂₁NO₉
• Molecular Weight: 383.355
• Mol file: 144427-71-4.mol

Synonyms:(E)-5,6,7,9-tetra-O-acetyl-4,8-anhydro-2,3-dideoxy-D-arabino-non-4-enononitrile

Chemical Property of (E)-5,6,7,9-tetra-O-acetyl-4,8-anhydro-2,3-dideoxy-D-arabino-non-4-enononitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-5,6,7,9-tetra-O-acetyl-4,8-anhydro-2,3-dideoxy-D-arabino-non-4-enononitrile

There total 2 articles about (E)-5,6,7,9-tetra-O-acetyl-4,8-anhydro-2,3-dideoxy-D-arabino-non-4-enononitrile 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: 25.0%

2,3,4,6-tetra-O-acetyl-1-bromo-β-D-glucopyranosyl chloride (112290-59-2) + acrylonitrile (107-13-1,25014-41-9) → 2,3,4,5-tetra-O-acetyl-D-glucopyranose (3947-62-4,6207-76-7,19235-21-3,22554-70-7,22860-22-6,47339-09-3,57884-82-9,62057-79-8,70191-05-8,109525-54-4,140147-37-1,10343-06-3) + (Z)-5,6,7,9-tetra-O-acetyl-4,8-anhydro-2,3-dideoxy-D-gluco-non-3-enononitrile (144427-70-3) + (4R)-5,6,7,9-tetra-O-acetyl-4,8-anhydro-4-chloro-2,3-dideoxy-D-glucononononitrile (144427-69-0) + (E)-5,6,7,9-tetra-O-acetyl-4,8-anhydro-2,3-dideoxy-D-arabino-non-4-enononitrile (144427-71-4) + 1-deoxy-D-glucose tetraacetate (13137-69-4) + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl chloride (4451-35-8)

Guidance literature:

With tri-n-butyl-tin hydride; In benzene; Product distribution; Mechanism; Heating; Irradiation; other solvents;

DOI:10.1016/S0008-6215(00)90998-4

Reference yield: 25.0%

2,3,4,6-tetra-O-acetyl-1-bromo-β-D-glucopyranosyl chloride (112290-59-2) + acrylonitrile (107-13-1,25014-41-9) → (Z)-5,6,7,9-tetra-O-acetyl-4,8-anhydro-2,3-dideoxy-D-gluco-non-3-enononitrile (144427-70-3) + (4R)-5,6,7,9-tetra-O-acetyl-4,8-anhydro-4-chloro-2,3-dideoxy-D-glucononononitrile (144427-69-0) + (E)-5,6,7,9-tetra-O-acetyl-4,8-anhydro-2,3-dideoxy-D-arabino-non-4-enononitrile (144427-71-4) + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl chloride (4451-35-8)

Guidance literature:

With tri-n-butyl-tin hydride; Heating; Irradiation;

DOI:10.1016/S0008-6215(00)90998-4

upstream raw materials:

2,3,4,6-tetra-O-acetyl-1-bromo-β-D-glucopyranosyl chloride

acrylonitrile