3-O-(2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl)-N-benzyloxycarbonyl-L-serine methyl ester

Base Information

• Chemical Name: 3-O-(2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl)-N-benzyloxycarbonyl-L-serine methyl ester
• CAS No.: 101301-69-3
• Molecular Formula: C₂₇H₃₂N₂O₁₀
• Molecular Weight: 544.558
• Mol file: 101301-69-3.mol

Synonyms:3-O-(2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl)-N-benzyloxycarbonyl-L-serine methyl ester

Chemical Property of 3-O-(2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl)-N-benzyloxycarbonyl-L-serine methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-O-(2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl)-N-benzyloxycarbonyl-L-serine methyl ester

There total 1 articles about 3-O-(2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl)-N-benzyloxycarbonyl-L-serine methyl ester 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: 70.0%

benzaldehyde dimethyl acetal (1125-88-8) + 3-O-(2-acetamido-2-deoxy-α-D-galactopyranosyl)-N-(benzyloxycarbonyl)-L-serine methyl ester (74084-39-2) → 3-O-(2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl)-N-benzyloxycarbonyl-L-serine methyl ester (101301-69-3)

Guidance literature:

With toluene-4-sulfonic acid; In N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0008-6215(00)90729-8

Reference yield:

3-O-(2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl)-N-benzyloxycarbonyl-L-serine methyl ester (101301-69-3) → 3-O-<2-acetamido-3-(β-D-galactopyranosyl)-2-deoxy-α-D-galactopyranosyl>-N-benzyloxycarbonyl-L-serine methyl ester (101301-62-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) mercuric cianide, calcium sulfate / 1.) acetonitrile, 30 min; 2.) 24 h

2: 91 percent / acetic acid / H₂O / 1 h / 75 °C

3: 93 percent / triethylamine / methanol / 8 h

With calcium sulfate; mercury(II) cyanide; acetic acid; triethylamine; In methanol; water;

DOI:10.1016/S0008-6215(00)90729-8

Reference yield:

3-O-(2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl)-N-benzyloxycarbonyl-L-serine methyl ester (101301-69-3) → 3-O-<2-acetamido-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2-deoxy-α-D-galactopyranosyl>-N-benzyloxycarbonyl-L-serine methyl ester (101301-67-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) mercuric cianide, calcium sulfate / 1.) acetonitrile, 30 min; 2.) 24 h

2: 91 percent / acetic acid / H₂O / 1 h / 75 °C

With calcium sulfate; mercury(II) cyanide; acetic acid; In water;

DOI:10.1016/S0008-6215(00)90729-8

upstream raw materials:

benzaldehyde dimethyl acetal

3-O-(2-acetamido-2-deoxy-α-D-galactopyranosyl)-N-(benzyloxycarbonyl)-L-serine methyl ester

Downstream raw materials:

3-O-<2-acetamido-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl>-N-benzyloxycarbonyl-L-serine methyl ester

3-O-<2-acetamido-3-(β-D-galactopyranosyl)-2-deoxy-α-D-galactopyranosyl>-N-benzyloxycarbonyl-L-serine methyl ester

3-O-<2-acetamido-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2-deoxy-α-D-galactopyranosyl>-N-benzyloxycarbonyl-L-serine methyl ester