methyl 2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside

Base Information

• Chemical Name: methyl 2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside
• CAS No.: 144789-65-1
• Molecular Formula: C₂₃H₂₇NO₆
• Molecular Weight: 413.47
• Mol file: 144789-65-1.mol

Synonyms:methyl 2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside

Chemical Property of methyl 2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside

There total 2 articles about methyl 2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-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: 71.0%

benzyl bromide (100-39-0) + methyl N-acetyl-2-amino-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside (6619-02-9,6619-04-1,10300-76-2,16727-56-3,17327-07-0,28978-56-5,52885-36-6,52885-45-7,78216-83-8,78513-50-5,87038-18-4,88295-36-7,110508-78-6,113159-04-9,117064-54-7,128657-61-4,129784-17-4,137330-28-0,78216-82-7) → methyl 2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside (144789-65-1) + methyl N-acetyl-N-benzyl-2-amino-2-deoxy-3-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside (354986-45-1)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 15h;

DOI:10.1021/ja010086b

Reference yield: 38.0%

phenyl 2,4-di-O-acetyl-3-O-benzyl-6-deoxy-6-dimethylphenylsilyl-1-thio-D-glucopyranoside + methyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside (85193-92-6) → methyl 2′,4′-di-O-acetyl-3′-O-benzyl-6′-deoxy-6′-dimethylphenylsilyl-β-D-glucopyranosyl-(1′→4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside + acetyl 2,4-di-O-acetyl-3-O-benzyl-6-deoxy-6-dimethylphenylsilyl-α-D-glucopyranoside + C25H32O7Si + methyl 2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside (144789-65-1)

Guidance literature:

With N-iodo-succinimide; trifluorormethanesulfonic acid; In dichloromethane; at -78 - 0 ℃; Inert atmosphere; Molecular sieve;

DOI:10.1002/ejoc.202000708

Reference yield: 84.0%

methyl 2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside (144789-65-1) → Methyl 2-amino-4,6-O-benzylidene-3-O-benzyl-2-deoxy-α-D-glucopyranoside (139573-22-1)

Guidance literature:

methyl 2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside; With pyridine; trifluoromethylsulfonic anhydride; In dichloromethane; at -40 - 0 ℃; for 6.5h;

With ethanol; In dichloromethane; at 0 - 20 ℃; Further stages.;

DOI:10.1039/b105872j

upstream raw materials:

benzyl bromide

methyl N-acetyl-2-amino-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside

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

Downstream raw materials:

Methyl 2-amino-4,6-O-benzylidene-3-O-benzyl-2-deoxy-α-D-glucopyranoside

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

methyl N,N-diacetyl-2-amino-2-deoxy-4,6-O-benzylidene-3-O-benzyl-α-D-glucopyranoside

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