3-(2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranosyl)propene

Base Information

• Chemical Name: 3-(2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranosyl)propene
• CAS No.: 1065524-59-5
• Molecular Formula: C₁₈H₂₃NO₅
• Molecular Weight: 333.384
• Mol file: 1065524-59-5.mol

Synonyms:3-(2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranosyl)propene

Chemical Property of 3-(2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranosyl)propene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-(2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranosyl)propene

There total 2 articles about 3-(2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranosyl)propene 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:

benzaldehyde (100-52-7) + 3-(2'-acetamido-3',4',6-tri-O-acetyl-2'-deoxy-α-D-glucopyranosyl)-1-propene (180778-36-3) → 3-(2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranosyl)propene (1065524-59-5)

Guidance literature:

3-(2'-acetamido-3',4',6-tri-O-acetyl-2'-deoxy-α-D-glucopyranosyl)-1-propene; With sodium methylate; In methanol; at 20 ℃;

benzaldehyde; With trifluoroacetic acid; at 20 ℃; for 3h;

DOI:10.1093/glycob/cwx017

Reference yield:

Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yl ester (3068-34-6) → 3-(2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranosyl)propene (1065524-59-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 2,2'-azobis(isobutyronitrile) / toluene / Reflux

2.1: sodium methylate / methanol / 20 °C

2.2: 3 h / 20 °C

With 2,2'-azobis(isobutyronitrile); sodium methylate; In methanol; toluene;

DOI:10.1093/glycob/cwx017

Reference yield: 97.0%

3-(2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranosyl)propene (1065524-59-5) + benzyl bromide (100-39-0) → C25H29NO5

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 1.5h;

DOI:10.1093/glycob/cwx017

upstream raw materials:

Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yl ester

benzaldehyde

3-(2'-acetamido-3',4',6-tri-O-acetyl-2'-deoxy-α-D-glucopyranosyl)-1-propene

Downstream raw materials:

3-(2-acetamido-4,6-O-benzylidene-2-deoxy-3-((R)-1-(methoxycarbonyl)ethoxy)-α-D-glucopyranosyl)propene

methyl 2-(2-acetamido-4,6-O-(R)-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-α-D-glucopyranosyl)acetate

dibenzyl 3-(2-acetamido-4,6-O-(R)-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-α-D-glucopyranosyl)-2-oxopropylphosphonate

benzyl 3-(2-acetamido-4,6-O-(R)-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-α-D-glucopyranosyl)-2-oxopropylphosphonate