allyl 2-acetamido-3-O-acetyl-4-O-benzyl-2-deoxy-6-O-tosyl-α-D-glucopyranoside

Base Information

• Chemical Name: allyl 2-acetamido-3-O-acetyl-4-O-benzyl-2-deoxy-6-O-tosyl-α-D-glucopyranoside
• CAS No.: 251324-20-6
• Molecular Formula: C₂₇H₃₃NO₉S
• Molecular Weight: 547.626
• Mol file: 251324-20-6.mol

Synonyms:allyl 2-acetamido-3-O-acetyl-4-O-benzyl-2-deoxy-6-O-tosyl-α-D-glucopyranoside

Chemical Property of allyl 2-acetamido-3-O-acetyl-4-O-benzyl-2-deoxy-6-O-tosyl-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of allyl 2-acetamido-3-O-acetyl-4-O-benzyl-2-deoxy-6-O-tosyl-α-D-glucopyranoside

There total 6 articles about allyl 2-acetamido-3-O-acetyl-4-O-benzyl-2-deoxy-6-O-tosyl-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: 72.0%

p-toluenesulfonyl chloride (98-59-9) + allyl 2-acetamido-3-O-acetyl-4-O-benzyl-2-deoxy-α-D-glucopyranoside (251324-19-3) → allyl 2-acetamido-3-O-acetyl-4-O-benzyl-2-deoxy-6-O-tosyl-α-D-glucopyranoside (251324-20-6)

Guidance literature:

With pyridine; dmap; at 20 ℃; for 6h;

DOI:10.1021/jo001183a

Reference yield:

allyl 2-acetamido-2-deoxy-α-D-glucopyranoside (54400-75-8) → allyl 2-acetamido-3-O-acetyl-4-O-benzyl-2-deoxy-6-O-tosyl-α-D-glucopyranoside (251324-20-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 86 percent / TsOH / dimethylformamide / 3 h / 60 °C / 10 Torr

2: 72 percent / pyridine; DMAP / 2.5 h / 20 °C

3: 90 percent / BH₃-NMe₃; Me₂BBr / CH₂Cl₂; toluene / 0.33 h / -78 °C

4: 72 percent / pyridine; DMAP / 6 h / 20 °C

With pyridine; dmap; dimethylboron bromide; trimethylamine-borane; toluene-4-sulfonic acid; In dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo001183a

Reference yield:

N-Acetyl-D-glucosamine (7512-17-6,72-87-7,1136-42-1,1136-44-3,6082-29-7,6730-06-9,7772-94-3,10036-64-3,14131-60-3,14131-64-7,14131-68-1,14215-68-0,62057-49-2,62057-50-5,62057-51-6,62057-52-7,62057-53-8,62057-54-9,62057-55-0,62057-56-1,62075-50-7,62137-54-6,134451-97-1,134522-12-6,148347-16-4) → allyl 2-acetamido-3-O-acetyl-4-O-benzyl-2-deoxy-6-O-tosyl-α-D-glucopyranoside (251324-20-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 63 percent / BF₃-Et₂O; HCl / 10 h / Heating

2: 86 percent / TsOH / dimethylformamide / 3 h / 60 °C / 10 Torr

3: 72 percent / pyridine; DMAP / 2.5 h / 20 °C

4: 90 percent / BH₃-NMe₃; Me₂BBr / CH₂Cl₂; toluene / 0.33 h / -78 °C

5: 72 percent / pyridine; DMAP / 6 h / 20 °C

With pyridine; hydrogenchloride; dmap; dimethylboron bromide; trimethylamine-borane; boron trifluoride diethyl etherate; toluene-4-sulfonic acid; In dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo001183a

upstream raw materials:

p-toluenesulfonyl chloride

allyl 2-acetamido-3-O-acetyl-4-O-benzyl-2-deoxy-α-D-glucopyranoside

allyl 2-acetamido-2-deoxy-α-D-glucopyranoside

N-Acetyl-D-glucosamine

Downstream raw materials:

allyl 2-acetamido-3-O-acetyl-6-azido-4-O-benzyl-2-deoxy-α-D-glucopyranoside