BENZYL 2-ACETAMIDO-3,4,6-TRI-O-BENZYL-2-DEOXY-ALPHA-D-GLUCOPYRANOSIDE

Base Information

• Chemical Name: BENZYL 2-ACETAMIDO-3,4,6-TRI-O-BENZYL-2-DEOXY-ALPHA-D-GLUCOPYRANOSIDE
• CAS No.: 38416-56-7
• Molecular Formula: C36H39NO6
• Molecular Weight: 581.709
• Mol file: 38416-56-7.mol

Synonyms:Benzyl2-acetamido-3,4,6-tri-O-benzyl-a-D-glucopyranoside;N-[(2S,3S,4R,5S)-2,4,5-tribenzyloxy-6-(benzyloxymethyl)tetrahydropyran-3-yl]acetamide;

Chemical Property of BENZYL 2-ACETAMIDO-3,4,6-TRI-O-BENZYL-2-DEOXY-ALPHA-D-GLUCOPYRANOSIDE

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 167-168°C
• Refractive Index: 1.609
• Boiling Point: 737.858 °C at 760 mmHg
• Flash Point: 400.042 °C
• PSA: 75.25000
• Density: 1.208 g/cm³
• LogP: 6.21130
• Storage Temp.: -20°C Freezer

Purity/Quality:

99%, ^*data from raw suppliers

2-Acetamido-1,3,4,6-tetra-O-benzyl-2-deoxy-a-D-glucopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of BENZYL 2-ACETAMIDO-3,4,6-TRI-O-BENZYL-2-DEOXY-ALPHA-D-GLUCOPYRANOSIDE

There total 11 articles about BENZYL 2-ACETAMIDO-3,4,6-TRI-O-BENZYL-2-DEOXY-ALPHA-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: 39.0%

benzyl 3-O-benzyl-2-acetamido-2-deoxy-α-D-glucopyranoside (14146-27-1) + benzyl bromide (100-39-0) → 3,4-di-O-benzyl-2-acetamido-2-desoxy-α-benzyl-D-glucopyranoside (55287-54-2) + benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside (55287-49-5) + 3,4,6-tri-O-benzyl-2-acetamido-2-desoxy-α-benzyl-D-glucopyranoside (38416-56-7)

Guidance literature:

With barium hydroxide octahydrate; barium(II) oxide; In N,N-dimethyl-formamide; at -5 ℃; for 4h;

DOI:10.1016/S0008-6215(00)80713-2

Reference yield: 12.0%

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) + acetic anhydride (108-24-7) + benzyl bromide (100-39-0) → Benzyl 2-N-acetylamino-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranoside (4171-69-1) + 3,4,6-tri-O-benzyl-2-acetamido-2-desoxy-α-benzyl-D-glucopyranoside (38416-56-7) + 3,4-di-O-acetyl-6-O-benzyl-2-deoxy-β-D-glucopyranoside (1610524-57-6) + benzyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside (10375-65-2,13318-46-2,13343-66-3,19374-72-2,33423-34-6,34029-78-2,41355-94-6,110911-57-4,141019-71-8)

Guidance literature:

N-Acetyl-D-glucosamine; With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 1.25h; Inert atmosphere;

benzyl bromide; In N,N-dimethyl-formamide; at 20 ℃; Inert atmosphere;

acetic anhydride; With pyridine;

DOI:10.1080/07328303.2014.907907

Reference yield: 5.0%

benzyl 3-O-benzyl-2-acetamido-2-deoxy-α-D-glucopyranoside (14146-27-1) + benzyl chloride (100-44-7) → 3,4-di-O-benzyl-2-acetamido-2-desoxy-α-benzyl-D-glucopyranoside (55287-54-2) + benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside (55287-49-5) + 3,4,6-tri-O-benzyl-2-acetamido-2-desoxy-α-benzyl-D-glucopyranoside (38416-56-7)

Guidance literature:

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

DOI:10.1007/BF00953238

upstream raw materials:

benzyl 3-O-benzyl-2-acetamido-2-deoxy-α-D-glucopyranoside

benzyl bromide

benzyl chloride

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

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