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

Base Information

• Chemical Name: 4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide
• CAS No.: 191037-58-8
• Molecular Formula: C₂₁H₁₈N₄O₆
• Molecular Weight: 422.397
• Mol file: 191037-58-8.mol

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

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

There total 5 articles about 4,6-O-benzylidene-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: 94.0%

benzaldehyde dimethyl acetal (1125-88-8) + 3,4,6-tri-O-acetyl-2-deoxy-2-N-phthalimido-β-D-glucopyranosyl azide (102816-24-0) → 4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide (191037-58-8)

Guidance literature:

With camphor-10-sulfonic acid; In acetonitrile; for 96h; Ambient temperature;

DOI:10.1002/(sici)1521-3765(19981102)4:11<2182::aid-chem2182>3.0.co;2-u

Reference yield: 78.0%

benzaldehyde dimethyl acetal (1125-88-8) + 2-deoxy-2-phthalimido-β-D-glucopyranosyl azide (102816-23-9) → 4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide (191037-58-8)

Guidance literature:

With toluene-4-sulfonic acid; In acetonitrile; at 20 ℃; for 1.75h; Inert atmosphere;

DOI:10.1002/ejoc.201200468

Reference yield:

1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose (10022-13-6) → 4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide (191037-58-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 84 percent / trimethylsilylazide, TMSOTf / acetonitrile / 4 h / Ambient temperature

2: 94 percent / DL-camphorsulfonic acid / acetonitrile / 96 h / Ambient temperature

With trimethylsilyl trifluoromethanesulfonate; trimethylsilylazide; camphor-10-sulfonic acid; In acetonitrile;

DOI:10.1002/(sici)1521-3765(19981102)4:11<2182::aid-chem2182>3.0.co;2-u

upstream raw materials:

benzaldehyde dimethyl acetal

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

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

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

Downstream raw materials:

C₂₂H₁₉F₃N₄O₈S

3-O-benzyl-2-deoxy-6-O-(p-methoxyphenyl)-2-phthalimido-β-D-glucopyranosyl azide

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

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