benzyl 2-acetamido-2-deoxy-3-O-methyl-6-O-p-tolylsulfonyl-α-D-glucopyranoside

Base Information

• Chemical Name: benzyl 2-acetamido-2-deoxy-3-O-methyl-6-O-p-tolylsulfonyl-α-D-glucopyranoside
• CAS No.: 93215-43-1
• Molecular Formula: C₂₃H₂₉NO₈S
• Molecular Weight: 479.551
• Mol file: 93215-43-1.mol

Synonyms:benzyl 2-acetamido-2-deoxy-3-O-methyl-6-O-p-tolylsulfonyl-α-D-glucopyranoside

Chemical Property of benzyl 2-acetamido-2-deoxy-3-O-methyl-6-O-p-tolylsulfonyl-α-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-methyl-6-O-p-tolylsulfonyl-α-D-glucopyranoside

There total 2 articles about benzyl 2-acetamido-2-deoxy-3-O-methyl-6-O-p-tolylsulfonyl-α-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: 76.0%

benzyl 2-acetamido-2-deoxy-3-O-methyl-α-D-glucopyranoside (93215-41-9) + p-toluenesulfonyl chloride (98-59-9) → benzyl 2-acetamido-2-deoxy-3-O-methyl-6-O-p-tolylsulfonyl-α-D-glucopyranoside (93215-43-1)

Guidance literature:

In pyridine; at 0 ℃; for 8h;

DOI:10.1016/0008-6215(84)85069-7

Reference yield:

benzyl 4,6-O-benzylidene-2-acetylamino-2-deoxy-α-D-glucopyranoside (13343-63-0) → benzyl 2-acetamido-2-deoxy-3-O-methyl-6-O-p-tolylsulfonyl-α-D-glucopyranoside (93215-43-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 52 percent / silver oxide / dimethylformamide / 6 h / Ambient temperature

2: 90 percent / 60 percent aq. acetic acid / 1 h / 100 °C

3: 76 percent / pyridine / 8 h / 0 °C

With acetic acid; silver(l) oxide; In pyridine; N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(84)85069-7

Reference yield: 76.0%

benzyl 2-acetamido-2-deoxy-3-O-methyl-6-O-p-tolylsulfonyl-α-D-glucopyranoside (93215-43-1) + sodium phenyl-methanolate (20194-18-7) → benzyl 2-acetamido-6-O-benzyl-2-deoxy-3-O-methyl-α-D-glucopyranoside (93215-44-2)

Guidance literature:

In N,N-dimethyl-formamide; benzyl alcohol; at 90 ℃; for 1h;

DOI:10.1016/0008-6215(84)85069-7

upstream raw materials:

benzyl 2-acetamido-2-deoxy-3-O-methyl-α-D-glucopyranoside

p-toluenesulfonyl chloride

benzyl 4,6-O-benzylidene-2-acetylamino-2-deoxy-α-D-glucopyranoside

Downstream raw materials:

benzyl 2-acetamido-6-O-benzyl-2-deoxy-3-O-methyl-α-D-glucopyranoside

benzyl 2-acetamido-6-O-benzyl-2-deoxy-4-O-β-D-galactopyranosyl-3-O-methyl-α-D-glucopyranoside

Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((2R,3S,4R,5R,6S)-5-acetylamino-6-benzyloxy-2-benzyloxymethyl-4-methoxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl ester