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

Base Information

• Chemical Name: methyl 2-acetamido-4,6-O-benzylidene-2-N,3-O-carbonyl-2-deoxy-α-D-glucopyranoside
• CAS No.: 526199-43-9
• Molecular Formula: C₁₇H₁₉NO₇
• Molecular Weight: 349.34

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

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

Chemical Property:

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

There total 2 articles about methyl 2-acetamido-4,6-O-benzylidene-2-N,3-O-carbonyl-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: 92.0%

acetyl chloride (75-36-5) + methyl 2-amino-4,6-O-benzylidene-2-N,3-O-carbonyl-2-deoxy-α-D-glucopyranoside (526199-42-8) → methyl 2-acetamido-4,6-O-benzylidene-2-N,3-O-carbonyl-2-deoxy-α-D-glucopyranoside (526199-43-9)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; for 6h;

DOI:10.1021/ol0342305

Reference yield:

methyl 2-amino-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside (128657-58-9) → methyl 2-acetamido-4,6-O-benzylidene-2-N,3-O-carbonyl-2-deoxy-α-D-glucopyranoside (526199-43-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: NaHCO₃ / H₂O; acetonitrile / 3 h / 0 °C

1.2: 76 percent / Amberlite IR-120NA / dimethylformamide / 20 °C

2.1: 92 percent / diisopropylethylamine / CH₂Cl₂ / 6 h

With sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine; In dichloromethane; water; acetonitrile;

DOI:10.1021/jo0482559

Reference yield: 80.0%

methyl 2-acetamido-4,6-O-benzylidene-2-N,3-O-carbonyl-2-deoxy-α-D-glucopyranoside (526199-43-9) → methyl 2-acetamido-6-O-benzyl-2-N,3-O-carbonyl-2-deoxy-α-D-glucopyranoside (526199-44-0)

Guidance literature:

With hydrogenchloride; methyl orange; sodium cyanoborohydride; In tetrahydrofuran; diethyl ether; at 0 ℃; for 1.5h;

DOI:10.1021/ol0342305

upstream raw materials:

acetyl chloride

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

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

Downstream raw materials:

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

methyl 2-acetamido-6-O-benzyl-2-N,3-O-carbonyl-2-deoxy-[2,3-O-carbonate-4-O-benzoyl-α-L-rhamnopyranosyl]-(1->4)-α-D-glucopyranoside

methyl 2-acetamido-6-O-benzyl-2-N,3-O-carbonyl-2-deoxy-[2,3-di-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl]-(1->4)-α-D-glucopyranoside

methyl 2-acetamido-6-O-benzyl-2-N,3-O-carbonyl-2-deoxy-[2,3-di-O-benzyl-4,6-O-benzylidene-α-D-glucopyranosyl]-(1->4)-α-D-glucopyranoside

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