4,6-O-benzylidene-3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide

Base Information

• Chemical Name: 4,6-O-benzylidene-3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide
• CAS No.: 191037-60-2
• Molecular Formula: C₂₈H₂₄N₄O₆
• Molecular Weight: 512.522
• Mol file: 191037-60-2.mol

Synonyms:4,6-O-benzylidene-3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide

Chemical Property of 4,6-O-benzylidene-3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4,6-O-benzylidene-3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide

There total 4 articles about 4,6-O-benzylidene-3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide 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: 83.0%

ethyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-N-phthalamido-1-thio-β-D-glucopyranoside (123212-53-3) → 4,6-O-benzylidene-3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide (191037-60-2)

Guidance literature:

With molecular sieve; trimethylsilylazide; methyl trifluoromethanesulfonate; In dichloromethane;

DOI:10.1016/S0040-4039(98)01540-8

Reference yield: 67.1%

benzyl bromide (100-39-0) + 4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide (191037-58-8) → 4,6-O-benzylidene-3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide (191037-60-2)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 0 - 20 ℃; for 3.5h; Inert atmosphere;

DOI:10.1002/ejoc.201200468

Reference yield:

2-deoxy-2-phthalimido-β-D-glucopyranosyl azide (102816-23-9) → 4,6-O-benzylidene-3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide (191037-60-2)

Guidance literature:

Multi-step reaction with 2 steps

1: toluene-4-sulfonic acid / acetonitrile / 1.75 h / 20 °C / Inert atmosphere

2: sodium hydride / N,N-dimethyl-formamide; mineral oil / 3.5 h / 0 - 20 °C / Inert atmosphere

With sodium hydride; toluene-4-sulfonic acid; In N,N-dimethyl-formamide; acetonitrile; mineral oil;

DOI:10.1002/ejoc.201200468

upstream raw materials:

ethyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-N-phthalamido-1-thio-β-D-glucopyranoside

3,4,6-tri-O-acetyl-2-deoxy-2-N-phthalimido-β-D-glucopyranosyl azide

2-deoxy-2-phthalimido-β-D-glucopyranosyl azide

benzyl bromide

Downstream raw materials:

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

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

3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide

C₂₂H₁₉F₃N₄O₈S