2-azido-3,6-dibenzyl-2-deoxy-4-phenoxyacetyl-α-D-glucopyranosyl-(1->6)-1-benzoyl-2,3,4,5-tetrabenzyl-myo-inositol

Base Information

• Chemical Name: 2-azido-3,6-dibenzyl-2-deoxy-4-phenoxyacetyl-α-D-glucopyranosyl-(1->6)-1-benzoyl-2,3,4,5-tetrabenzyl-myo-inositol
• CAS No.: 502689-59-0
• Molecular Formula: C₆₉H₆₇N₃O₁₃
• Molecular Weight: 1146.3
• Mol file: 502689-59-0.mol

Synonyms:2-azido-3,6-dibenzyl-2-deoxy-4-phenoxyacetyl-α-D-glucopyranosyl-(1->6)-1-benzoyl-2,3,4,5-tetrabenzyl-myo-inositol

Chemical Property of 2-azido-3,6-dibenzyl-2-deoxy-4-phenoxyacetyl-α-D-glucopyranosyl-(1->6)-1-benzoyl-2,3,4,5-tetrabenzyl-myo-inositol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-azido-3,6-dibenzyl-2-deoxy-4-phenoxyacetyl-α-D-glucopyranosyl-(1->6)-1-benzoyl-2,3,4,5-tetrabenzyl-myo-inositol

There total 4 articles about 2-azido-3,6-dibenzyl-2-deoxy-4-phenoxyacetyl-α-D-glucopyranosyl-(1->6)-1-benzoyl-2,3,4,5-tetrabenzyl-myo-inositol 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: 88.0%

benzoyl cyanide (613-90-1) + 2-azido-3,6-dibenzyl-2-deoxy-4-phenoxyacetyl-α-D-glucopyranosyl-(1->6)-2,3,4,5-tetrabenzyl-myo-inositol (502689-58-9) → 2-azido-3,6-dibenzyl-2-deoxy-4-phenoxyacetyl-α-D-glucopyranosyl-(1->6)-1-benzoyl-2,3,4,5-tetrabenzyl-myo-inositol (502689-59-0)

Guidance literature:

With triethylamine; In dichloromethane; for 2h;

DOI:10.1021/jo026380j

Reference yield:

Phenoxyacetyl chloride (701-99-5) → 2-azido-3,6-dibenzyl-2-deoxy-4-phenoxyacetyl-α-D-glucopyranosyl-(1->6)-1-benzoyl-2,3,4,5-tetrabenzyl-myo-inositol (502689-59-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 83 percent / pyridine / 0 - 20 °C

2: 96 percent / cerium(IV) ammonium nitrate / acetonitrile; toluene; H₂O / 2 h / 0 - 20 °C

3: 88 percent / triethylamine / CH₂Cl₂ / 2 h

With pyridine; ammonium cerium(IV) nitrate; triethylamine; In dichloromethane; water; toluene; acetonitrile;

DOI:10.1021/jo026380j

Reference yield:

(2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->6)-2,3,4,5-tetra-O-benzyl-1-O-(4-methoxybenzyl)-D-myo-inositol (220734-77-0) → 2-azido-3,6-dibenzyl-2-deoxy-4-phenoxyacetyl-α-D-glucopyranosyl-(1->6)-1-benzoyl-2,3,4,5-tetrabenzyl-myo-inositol (502689-59-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 83 percent / pyridine / 0 - 20 °C

2: 96 percent / cerium(IV) ammonium nitrate / acetonitrile; toluene; H₂O / 2 h / 0 - 20 °C

3: 88 percent / triethylamine / CH₂Cl₂ / 2 h

With pyridine; ammonium cerium(IV) nitrate; triethylamine; In dichloromethane; water; toluene; acetonitrile;

DOI:10.1021/jo026380j

upstream raw materials:

benzoyl cyanide

2-azido-3,6-dibenzyl-2-deoxy-4-phenoxyacetyl-α-D-glucopyranosyl-(1->6)-2,3,4,5-tetrabenzyl-myo-inositol

Phenoxyacetyl chloride

(2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->6)-2,3,4,5-tetra-O-benzyl-1-O-(4-methoxybenzyl)-D-myo-inositol

Downstream raw materials:

2-azido-3,6-dibenzyl-2-deoxy-α-D-glucopyranosyl-(1->6)-1-benzoyl-2,3,4,5-tetrabenzyl-myo-inositol

Benzoic acid (1R,2R,3R,4R,5S,6R)-2,3,4,5-tetrakis-benzyloxy-6-((2R,3R,4R,5S,6R)-4-benzyloxy-6-benzyloxymethyl-3-tert-butoxycarbonylamino-5-hydroxy-tetrahydro-pyran-2-yloxy)-cyclohexyl ester