methyl 2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside

Base Information

• Chemical Name: methyl 2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside
• CAS No.: 1371585-28-2
• Molecular Formula: C₃₁H₄₂N₂O₁₁
• Molecular Weight: 618.681
• Mol file: 1371585-28-2.mol

Synonyms:methyl 2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside

Chemical Property of methyl 2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside

There total 12 articles about methyl 2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->4)-2-acetamido-3,6-di-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: 100.0%

methyl 2-amino-2-deoxy-β-D-glucopyranosyl-(1->4)-2-amino-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside (1371585-27-1) + acetic anhydride (108-24-7) → methyl 2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside (1371585-28-2)

Guidance literature:

In methanol; at 0 - 20 ℃;

DOI:10.1039/c2ob07066a

Reference yield:

1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose (10022-13-6) → methyl 2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside (1371585-28-2)

Guidance literature:

Multi-step reaction with 10 steps

1.1: boron trifluoride diethyl etherate / chloroform / 0.17 h / 0 - 20 °C / Inert atmosphere

1.2: 2 h / 20 °C / Inert atmosphere

2.1: methanol; sodium methylate / 1.5 h / 20 °C / pH 9

3.1: toluene-4-sulfonic acid / N,N-dimethyl-formamide / 20 - 50 °C

4.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / Inert atmosphere

4.2: 20 °C / Inert atmosphere

5.1: hydrogenchloride; sodium cyanoborohydride / tetrahydrofuran; diethyl ether / 5 h / 0 - 20 °C / Molecular sieve

6.1: N-iodo-succinimide; silver trifluoromethanesulfonate / dichloromethane / 0.17 h / 20 °C / Inert atmosphere

7.1: N-iodo-succinimide; silver trifluoromethanesulfonate / dichloromethane / 0.25 h / 20 °C / Molecular sieve; Inert atmosphere

8.1: methanol; sodium methylate / 0.5 h / 20 °C / pH 9 - 10

9.1: ethylenediamine / ethanol / 1.5 h / Reflux

10.1: methanol / 0 - 20 °C

With hydrogenchloride; methanol; N-iodo-succinimide; boron trifluoride diethyl etherate; sodium methylate; silver trifluoromethanesulfonate; sodium hydride; sodium cyanoborohydride; toluene-4-sulfonic acid; ethylenediamine; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; chloroform; N,N-dimethyl-formamide; mineral oil;

DOI:10.1039/c2ob07066a

Reference yield:

ethyl-3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (99409-32-2) → methyl 2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside (1371585-28-2)

Guidance literature:

Multi-step reaction with 4 steps

1: N-iodo-succinimide; silver trifluoromethanesulfonate / dichloromethane / 0.25 h / 20 °C / Molecular sieve; Inert atmosphere

2: methanol; sodium methylate / 0.5 h / 20 °C / pH 9 - 10

3: ethylenediamine / ethanol / 1.5 h / Reflux

4: methanol / 0 - 20 °C

With methanol; N-iodo-succinimide; sodium methylate; silver trifluoromethanesulfonate; ethylenediamine; In methanol; ethanol; dichloromethane;

DOI:10.1039/c2ob07066a

upstream raw materials:

1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose

methyl 2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

methyl 2-amino-2-deoxy-β-D-glucopyranosyl-(1->4)-2-amino-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside

acetic anhydride

Downstream raw materials:

methyl-N,N'-diacetyl-β-chitobioside