benzyl 2-acetamido-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside

Base Information

• Chemical Name: benzyl 2-acetamido-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside
• CAS No.: 58902-39-9
• Molecular Formula: C₂₉H₃₉NO₁₅
• Molecular Weight: 641.626
• Mol file: 58902-39-9.mol

Synonyms:benzyl 2-acetamido-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside

Chemical Property of benzyl 2-acetamido-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl 2-acetamido-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside

There total 5 articles about benzyl 2-acetamido-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside 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: 92.0%

benzyl 2-acetamido-2-deoxy-4,6-O-isopropylidene-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside (80035-18-3) → benzyl 2-acetamido-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside (58902-39-9,60831-31-4)

Guidance literature:

With perchloric acid; In dichloromethane; water; at 0 - 5 ℃; for 1h;

Reference yield:

benzyl 2-acetamido-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside (50605-12-4) → benzyl 2-acetamido-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside (58902-39-9,60831-31-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 73 percent / mercuric cyanide / acetonitrile / 8 h / Ambient temperature

2: 79 percent / acetic acid (80percent) / 0.5 h / 100 °C

With mercury(II) cyanide; acetic acid; In acetonitrile;

DOI:10.1016/S0008-6215(00)81873-X

Reference yield:

benzyl 2-acetamido-2-deoxy-β-D-glucopyranoside (3055-51-4,3554-93-6,10380-86-6,13343-62-9,13343-67-4,19374-70-0,33423-30-2,33501-36-9,41355-95-7,86834-14-2,111003-11-3,347411-88-5) → benzyl 2-acetamido-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside (58902-39-9,60831-31-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 68 percent / p-toluenesulfonic acid / dimethylformamide / 4 h / Ambient temperature

2: 73 percent / mercuric cyanide / acetonitrile / 8 h / Ambient temperature

3: 79 percent / acetic acid (80percent) / 0.5 h / 100 °C

With mercury(II) cyanide; toluene-4-sulfonic acid; acetic acid; In N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0008-6215(00)81873-X

upstream raw materials:

benzyl 2-acetamido-2-deoxy-4,6-O-isopropylidene-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside

benzyl 2-acetamido-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside

benzyl 2-acetamido-2-deoxy-β-D-glucopyranoside

2,3,4,6-tetra-O-acetyl-α-galactopyranosyl trichloroacetimidate

Downstream raw materials:

C₇₁H₇₃NO₂₂

benzyl 3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2-acetamido-4,6-di-O-benzoyl-2-deoxy-β-D-galactopyranoside

benzyl 3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2-acetamido-6-O-benzoyl-2-deoxy-β-D-glucopyranoside

Acetic acid (2R,3S,4R,5R,6R)-5-acetylamino-6-benzyloxy-3-hydroxy-4-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylmethyl ester