benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-allopyranoside-2,3-sulfamidate

Base Information

• Chemical Name: benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-allopyranoside-2,3-sulfamidate
• CAS No.: 176167-82-1
• Molecular Formula: C₂₂H₂₃NO₈S
• Molecular Weight: 461.493
• Mol file: 176167-82-1.mol

Synonyms:benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-allopyranoside-2,3-sulfamidate

Chemical Property of benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-allopyranoside-2,3-sulfamidate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-allopyranoside-2,3-sulfamidate

There total 13 articles about benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-allopyranoside-2,3-sulfamidate 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: 88.0%

benzyl 4,6-O-benzylidene-2-deoxy-β-D-allopyranoside-2,3-sulfamidate + acetyl chloride (75-36-5) → benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-allopyranoside-2,3-sulfamidate (176167-82-1)

Guidance literature:

With pyridine; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1016/j.bmc.2018.10.008

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-4,6-O-benzylidene-2-deoxy-β-D-allopyranoside-2,3-sulfamidate (176167-82-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 85 percent / Ph₃P, DEAD / tetrahydrofuran / 1.5 h / 65 °C

2: NaOMe / methanol / 1 h / Ambient temperature

3: p-TsOH / acetonitrile / 2 h / Ambient temperature

4: 1.) NaH, 1,1'-sulfuryl-diimidazole, 2.) pyridine / 1.) DMF, -40 deg C to r.t., 1 h, 2.) CH₂Cl₂, r.t., 2 h

With pyridine; sodium methylate; sodium hydride; toluene-4-sulfonic acid; triphenylphosphine; N,N`-sulfuryldiimidazole; diethylazodicarboxylate; In tetrahydrofuran; methanol; acetonitrile;

DOI:10.1039/CC9960000127

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) → benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-allopyranoside-2,3-sulfamidate (176167-82-1)

Guidance literature:

Multi-step reaction with 2 steps

1: p-TsOH / acetonitrile / 2 h / Ambient temperature

2: 1.) NaH, 1,1'-sulfuryl-diimidazole, 2.) pyridine / 1.) DMF, -40 deg C to r.t., 1 h, 2.) CH₂Cl₂, r.t., 2 h

With pyridine; sodium hydride; toluene-4-sulfonic acid; N,N`-sulfuryldiimidazole; In acetonitrile;

DOI:10.1039/CC9960000127

upstream raw materials:

acetyl chloride

benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-allopyranoside

benzaldehyde dimethyl acetal

N-((2R,3R,4S,5S,6R)-2-Benzyloxy-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl)-acetamide