3-O-benzoyl-3-C-cyano-1,2:4,5-di-O-isopropylidene-β-D-psicopyranose

Base Information

• Chemical Name: 3-O-benzoyl-3-C-cyano-1,2:4,5-di-O-isopropylidene-β-D-psicopyranose
• CAS No.: 532394-78-8
• Molecular Formula: C₂₀H₂₃NO₇
• Molecular Weight: 389.405
• Mol file: 532394-78-8.mol

Synonyms:3-O-benzoyl-3-C-cyano-1,2:4,5-di-O-isopropylidene-β-D-psicopyranose

Chemical Property of 3-O-benzoyl-3-C-cyano-1,2:4,5-di-O-isopropylidene-β-D-psicopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-O-benzoyl-3-C-cyano-1,2:4,5-di-O-isopropylidene-β-D-psicopyranose

There total 2 articles about 3-O-benzoyl-3-C-cyano-1,2:4,5-di-O-isopropylidene-β-D-psicopyranose 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: 60.0%

1,2:4,5-di-O-isopropylidene-3-C-cyano-β-D-psicopyranose (144486-09-9) + benzoyl chloride (98-88-4) → 1,2:4,5-di-O-isopropylidene-3-C-cyano-3-O-benzoyl-β-D-fructopyranose + 3-O-benzoyl-3-C-cyano-1,2:4,5-di-O-isopropylidene-β-D-psicopyranose (532394-78-8)

Guidance literature:

With pyridine; In dichloromethane; at 0 - 20 ℃;

DOI:10.1016/j.bmc.2004.10.023

Reference yield:

Shi's ketone (69351-19-5,18422-53-2) → 3-O-benzoyl-3-C-cyano-1,2:4,5-di-O-isopropylidene-β-D-psicopyranose (532394-78-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 97 percent / tetrabutylammonium bromide / CH₂Cl₂; H₂O / 20 °C

2: 60 percent / pyridine / CH₂Cl₂ / 0 - 20 °C

With pyridine; tetrabutylammomium bromide; In dichloromethane; water;

DOI:10.1016/j.bmc.2004.10.023

Reference yield: 58.0%

3-O-benzoyl-3-C-cyano-1,2:4,5-di-O-isopropylidene-β-D-psicopyranose (532394-78-8) → 3-O-benzoyl-3-C-(N-hydroxycarbamimidoyl)-1,2:4,5-di-O-isopropylidene-β-D-psicopyranose (532394-79-9)

Guidance literature:

With hydroxylamine; In methanol; for 8h; Heating;

DOI:10.1016/S0008-6215(02)00401-9

upstream raw materials:

1,2:4,5-di-O-isopropylidene-3-C-cyano-β-D-psicopyranose

benzoyl chloride

Shi's ketone

Downstream raw materials:

3-O-benzoyl-3-C-(N-hydroxycarbamimidoyl)-1,2:4,5-di-O-isopropylidene-β-D-psicopyranose

1,2:4,5-di-O-isopropylidene-3-C-(5-phenyl-1,2,4-oxadiazol-3-yl)-β-D-psicopyranose

Refernces