allyl 2-acetamido-6-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-3-O-benzoyl-4-O-benzyl-2-deoxy-β-D-glucopyranoside

Base Information

• Chemical Name: allyl 2-acetamido-6-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-3-O-benzoyl-4-O-benzyl-2-deoxy-β-D-glucopyranoside
• CAS No.: 92949-53-6
• Molecular Formula: C₃₉H₄₈N₂O₁₅
• Molecular Weight: 784.815
• Mol file: 92949-53-6.mol

Synonyms:allyl 2-acetamido-6-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-3-O-benzoyl-4-O-benzyl-2-deoxy-β-D-glucopyranoside

Chemical Property of allyl 2-acetamido-6-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-3-O-benzoyl-4-O-benzyl-2-deoxy-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of allyl 2-acetamido-6-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-3-O-benzoyl-4-O-benzyl-2-deoxy-β-D-glucopyranoside

There total 13 articles about allyl 2-acetamido-6-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-3-O-benzoyl-4-O-benzyl-2-deoxy-β-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: 64.0%

allyl 2-acetamido-3-O-benzoyl-4-O-benzyl-2-deoxy-β-D-glucopyranoside (92949-52-5) + 2-methyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-glucopyranoso)[1,2-d]-2-oxazoline (10378-06-0,20757-53-3,35954-65-5,123483-77-2,134308-33-1) → allyl 2-acetamido-6-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-3-O-benzoyl-4-O-benzyl-2-deoxy-β-D-glucopyranoside (92949-53-6)

Guidance literature:

With toluene-4-sulfonic acid; In chloroform; for 7h; Heating;

DOI:10.1016/S0040-4039(01)81258-2

Reference yield:

allyl 2-acetamido-2-deoxy-β-D-glucopyranoside (54400-75-8,64650-83-5,88903-97-3,116347-86-5,140849-88-3,144300-01-6,54400-77-0) → allyl 2-acetamido-6-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-3-O-benzoyl-4-O-benzyl-2-deoxy-β-D-glucopyranoside (92949-53-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 69 percent / pyridine; tetrahydrofuran / 1 h / -60 °C

2: 1.) trifluoromethanesulfonic acid, 2.) 1M hydrochloric acid, 3.) acetic anhydride, triethylamine / 1.) CH₂Cl₂, 4 deg C, 2.) THF, room temp. 3.) THF, room temp.

3: 79 percent / 0.02 M sodium methoxyde / 6 h / 0 °C

4: 64 percent / p-toluenesulfonic acid / CHCl₃ / 7 h / Heating

With hydrogenchloride; trifluorormethanesulfonic acid; sodium methylate; acetic anhydride; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; pyridine; chloroform;

DOI:10.1246/bcsj.60.2197

Reference yield:

allyl 2-acetamido-3,6-di-O-benzoyl-2-deoxy-β-D-glucopyranoside (70834-40-1) → allyl 2-acetamido-6-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-3-O-benzoyl-4-O-benzyl-2-deoxy-β-D-glucopyranoside (92949-53-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) trifluoromethanesulfonic acid, 2.) 1M hydrochloric acid, 3.) acetic anhydride, triethylamine / 1.) CH₂Cl₂, 4 deg C, 2.) THF, room temp. 3.) THF, room temp.

2: 79 percent / 0.02 M sodium methoxyde / 6 h / 0 °C

3: 64 percent / p-toluenesulfonic acid / CHCl₃ / 7 h / Heating

With hydrogenchloride; trifluorormethanesulfonic acid; sodium methylate; acetic anhydride; toluene-4-sulfonic acid; triethylamine; In chloroform;

DOI:10.1246/bcsj.60.2197

upstream raw materials:

acetic anhydride

allyl 2-acetamido-3-O-benzoyl-4-O-benzyl-2-deoxy-β-D-glucopyranoside

2-methyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-glucopyranoso)[1,2-d]-2-oxazoline

allyl 2-acetamido-3,6-di-O-benzoyl-2-deoxy-β-D-glucopyranoside

Downstream raw materials:

allyl 6-O-<3,4,6-tri-O-acetyl-2-<(R)-3-benzyloxytetradecanoylamino>-2-deoxy-β-D-glucopyranosyl>-3-O-benzoyl-4-O-benzyl-2-<(R)-3-benzyloxytetradecanoylamino>-2-deoxy-β-D-glucopyranoside

allyl 4-O-benzyl-2-<(R)-3-benzyloxytetradecanoylamino>-6-O-<2-<(R)-3-benzyloxytetradecanoylamino>-2-deoxy-β-D-glucopyranosyl>-2-deoxy-β-D-glucopyranoside

allyl 4-O-benzyl-2-<(R)-3-benzyloxytetradecanoylamino>-6-O-<2-<(R)-3-benzyloxytetradecanoylamino>-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranosyl>-2-deoxy-β-D-glucopyranoside

Benzoic acid (2R,3R,4R,5S,6R)-2-allyloxy-3-amino-5-benzyloxy-6-((2R,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-amino-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-4-yl ester