1-O-benzyl-4,6-O-diacetyl-3-O-((R)-phenylsulfonylethyl-propion-2-yl)-N-acetyl-α-D-glucosamine

Base Information

• Chemical Name: 1-O-benzyl-4,6-O-diacetyl-3-O-((R)-phenylsulfonylethyl-propion-2-yl)-N-acetyl-α-D-glucosamine
• CAS No.: 202464-71-9
• Molecular Formula: C₃₀H₃₇NO₁₂S
• Molecular Weight: 635.689

Synonyms:1-O-benzyl-4,6-O-diacetyl-3-O-((R)-phenylsulfonylethyl-propion-2-yl)-N-acetyl-α-D-glucosamine

Chemical Property of 1-O-benzyl-4,6-O-diacetyl-3-O-((R)-phenylsulfonylethyl-propion-2-yl)-N-acetyl-α-D-glucosamine

Chemical Property:

Purity/Quality:

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Technology Process of 1-O-benzyl-4,6-O-diacetyl-3-O-((R)-phenylsulfonylethyl-propion-2-yl)-N-acetyl-α-D-glucosamine

There total 8 articles about 1-O-benzyl-4,6-O-diacetyl-3-O-((R)-phenylsulfonylethyl-propion-2-yl)-N-acetyl-α-D-glucosamine 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: 85.0%

acetic anhydride (108-24-7) + benzyl 2-acetamido-2-deoxy-3-O-(D-1-{[2-(phenylsulfonyl)ethoxy]carbonyl}ethyl)-α-D-glucopyranoside (917029-90-4) → 1-O-benzyl-4,6-O-diacetyl-3-O-((R)-phenylsulfonylethyl-propion-2-yl)-N-acetyl-α-D-glucosamine (202464-71-9)

Guidance literature:

In pyridine; at 20 ℃; for 3h;

DOI:10.1021/ja302099u

Reference yield:

benzyl 2-acetamido-4,6-O-benzylidene-3-O-[(R)-1-carboxyethyl]-2-deoxy-α-D-glucopyranoside (73089-68-6) → 1-O-benzyl-4,6-O-diacetyl-3-O-((R)-phenylsulfonylethyl-propion-2-yl)-N-acetyl-α-D-glucosamine (202464-71-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / EDCI; DMAP / CH₂Cl₂

2: aq. AcOH / Heating

3: pyridine

With pyridine; dmap; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane;

DOI:10.1021/ja016082o

Reference yield:

2-(phenylsulfonyl)ethanol (20611-21-6) → 1-O-benzyl-4,6-O-diacetyl-3-O-((R)-phenylsulfonylethyl-propion-2-yl)-N-acetyl-α-D-glucosamine (202464-71-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / EDCI; DMAP / CH₂Cl₂

2: aq. AcOH / Heating

3: pyridine

With pyridine; dmap; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane;

DOI:10.1021/ja016082o

upstream raw materials:

acetic anhydride

benzyl 2-acetamido-2-deoxy-3-O-(D-1-{[2-(phenylsulfonyl)ethoxy]carbonyl}ethyl)-α-D-glucopyranoside

2-(phenylsulfonyl)ethanol

benzyl 2-acetamido-4,6-O-benzylidene-3-O-[(R)-1-carboxyethyl]-2-deoxy-α-D-glucopyranoside

Downstream raw materials:

4,6-O-diacetyl-3-O-((R)-phenylsulfonylethyl-propion-2-yl)-N-acetyl-α-D-glucosamine

C₅₃H₇₃F₃N₇O₂₁P

(R)-2-[(2R,3S,4R,5R,6R)-3-Acetoxy-2-acetoxymethyl-5-acetylamino-6-(bis-benzyloxy-phosphoryloxy)-tetrahydro-pyran-4-yloxy]-propionic acid

di-O-benzyl 4,6-O-diacetyl-3-O-((R)-phenylsulfonylethylpropion-2-yl)-N-acetyl-α-D-glucosamine-1-phosphate

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