2-azido-3,6-di-O-benzyl-2-deoxy-4-O-p-methoxybenzyl-α-D-glucopyranosyl-(1-4)-methyl-1,2-di-O-acetyl-3-O-benzyl-β-L-idopyranuronate

Base Information

• Chemical Name: 2-azido-3,6-di-O-benzyl-2-deoxy-4-O-p-methoxybenzyl-α-D-glucopyranosyl-(1-4)-methyl-1,2-di-O-acetyl-3-O-benzyl-β-L-idopyranuronate
• CAS No.: 1394857-47-6
• Molecular Formula: C₄₆H₅₁N₃O₁₄
• Molecular Weight: 869.923
• Mol file: 1394857-47-6.mol

Synonyms:

Chemical Property of 2-azido-3,6-di-O-benzyl-2-deoxy-4-O-p-methoxybenzyl-α-D-glucopyranosyl-(1-4)-methyl-1,2-di-O-acetyl-3-O-benzyl-β-L-idopyranuronate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-azido-3,6-di-O-benzyl-2-deoxy-4-O-p-methoxybenzyl-α-D-glucopyranosyl-(1-4)-methyl-1,2-di-O-acetyl-3-O-benzyl-β-L-idopyranuronate

There total 14 articles about 2-azido-3,6-di-O-benzyl-2-deoxy-4-O-p-methoxybenzyl-α-D-glucopyranosyl-(1-4)-methyl-1,2-di-O-acetyl-3-O-benzyl-β-L-idopyranuronate 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:

2-deoxy-2-trichloroacetamido-α/β-D-glucopyranose → C46H51N3O14 (915154-77-7) + 2-azido-3,6-di-O-benzyl-2-deoxy-4-O-p-methoxybenzyl-α-D-glucopyranosyl-(1-4)-methyl-1,2-di-O-acetyl-3-O-benzyl-β-L-idopyranuronate (1394857-47-6)

Guidance literature:

Multi-step reaction with 10 steps

1.1: pyridine / dichloromethane / 16 h / 0 - 20 °C

2.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 18 h / 20 °C / Inert atmosphere

3.1: methanol; sodium / Inert atmosphere

4.1: camphorsulfonic acid / tetrahydrofuran / 2 h / Dean-Stark; Reflux

5.1: potassium hydroxide; water / tetrahydrofuran; methanol / 2 h

6.1: imidazole-1-sulfonyl azide hydrochloride; copper(ll) sulfate pentahydrate; potassium carbonate / tetrahydrofuran; methanol / 5 h

7.1: sodium hydride / tetrahydrofuran / 1.5 h / 20 °C

7.2: 3 h / 50 °C

8.1: boron trifluoride diethyl etherate; triethylsilane / dichloromethane / 4 h / 0 °C / Inert atmosphere

9.1: sodium hydride / tetrahydrofuran; mineral oil / 60 °C / Inert atmosphere

10.1: N-iodo-succinimide; silver trifluoromethanesulfonate / dichloromethane / 0 °C / Molecular sieve

With pyridine; methanol; triethylsilane; imidazole-1-sulfonyl azide hydrochloride; N-iodo-succinimide; copper(ll) sulfate pentahydrate; trimethylsilyl trifluoromethanesulfonate; camphorsulfonic acid; boron trifluoride diethyl etherate; water; silver trifluoromethanesulfonate; sodium; sodium hydride; potassium carbonate; potassium hydroxide; In tetrahydrofuran; methanol; dichloromethane; mineral oil;

DOI:10.1021/jo300722y

Reference yield:

1,3,4,6-tetra-O-acetyl-2-deoxy-2-(2,2,2-trichloroacetamido)-β-D-glucopyranose (56644-75-8,10353-00-1) → C46H51N3O14 (915154-77-7) + 2-azido-3,6-di-O-benzyl-2-deoxy-4-O-p-methoxybenzyl-α-D-glucopyranosyl-(1-4)-methyl-1,2-di-O-acetyl-3-O-benzyl-β-L-idopyranuronate (1394857-47-6)

Guidance literature:

Multi-step reaction with 8 steps

1.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 18 h / 20 °C / Inert atmosphere

2.1: potassium carbonate; water / methanol / 18 h / 60 °C

3.1: imidazole-1-sulfonyl azide hydrochloride; copper(ll) sulfate pentahydrate; potassium carbonate / methanol / 2.67 h / 20 °C

4.1: toluene-4-sulfonic acid / acetonitrile / 72 h / 20 °C

5.1: sodium hydride / tetrahydrofuran / 1.5 h / 20 °C

5.2: 3 h / 50 °C

6.1: boron trifluoride diethyl etherate; triethylsilane / dichloromethane / 4 h / 0 °C / Inert atmosphere

7.1: sodium hydride / tetrahydrofuran; mineral oil / 60 °C / Inert atmosphere

8.1: N-iodo-succinimide; silver trifluoromethanesulfonate / dichloromethane / 0 °C / Molecular sieve

With triethylsilane; imidazole-1-sulfonyl azide hydrochloride; N-iodo-succinimide; copper(ll) sulfate pentahydrate; trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; water; silver trifluoromethanesulfonate; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; dichloromethane; acetonitrile; mineral oil;

DOI:10.1021/jo300722y

Reference yield:

phenyl 3,4,6-tri-O-acetyl-2-deoxy-1-thio-2-trichloroacetamido-β-D-glucopyranoside (169557-87-3) → C46H51N3O14 (915154-77-7) + 2-azido-3,6-di-O-benzyl-2-deoxy-4-O-p-methoxybenzyl-α-D-glucopyranosyl-(1-4)-methyl-1,2-di-O-acetyl-3-O-benzyl-β-L-idopyranuronate (1394857-47-6)

Guidance literature:

Multi-step reaction with 7 steps

1.1: potassium carbonate; water / methanol / 18 h / 60 °C

2.1: imidazole-1-sulfonyl azide hydrochloride; copper(ll) sulfate pentahydrate; potassium carbonate / methanol / 2.67 h / 20 °C

3.1: toluene-4-sulfonic acid / acetonitrile / 72 h / 20 °C

4.1: sodium hydride / tetrahydrofuran / 1.5 h / 20 °C

4.2: 3 h / 50 °C

5.1: boron trifluoride diethyl etherate; triethylsilane / dichloromethane / 4 h / 0 °C / Inert atmosphere

6.1: sodium hydride / tetrahydrofuran; mineral oil / 60 °C / Inert atmosphere

7.1: N-iodo-succinimide; silver trifluoromethanesulfonate / dichloromethane / 0 °C / Molecular sieve

With triethylsilane; imidazole-1-sulfonyl azide hydrochloride; N-iodo-succinimide; copper(ll) sulfate pentahydrate; boron trifluoride diethyl etherate; water; silver trifluoromethanesulfonate; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; dichloromethane; acetonitrile; mineral oil;

DOI:10.1021/jo300722y

upstream raw materials:

phenyl 2-amino-2-deoxy-1-thio-β-D-glucopyranoside

(+)-D-glucosamine hydrochloride

phenyl 3,4,6-tri-O-acetyl-2-deoxy-1-thio-2-trichloroacetamido-β-D-glucopyranoside

1,3,4,6-tetra-O-acetyl-2-deoxy-2-(2,2,2-trichloroacetamido)-β-D-glucopyranose