3-Azidopropyl O-(3-O-benzyl-6-O-chloroacetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside

Base Information

• Chemical Name: 3-Azidopropyl O-(3-O-benzyl-6-O-chloroacetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside
• CAS No.: 177421-34-0
• Molecular Formula: C₅₀H₅₉ClN₄O₂₄
• Molecular Weight: 1135.48
• Mol file: 177421-34-0.mol

Synonyms:

Chemical Property of 3-Azidopropyl O-(3-O-benzyl-6-O-chloroacetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-Azidopropyl O-(3-O-benzyl-6-O-chloroacetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside

There total 12 articles about 3-Azidopropyl O-(3-O-benzyl-6-O-chloroacetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-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: 56.0%

3-Azidopropyl O-(3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside (177421-33-9) + Chloroacetic anhydride (541-88-8) → 3-Azidopropyl O-(3-O-benzyl-6-O-chloroacetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside (177421-34-0)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; Ambient temperature;

DOI:10.1080/07328309608005653

Reference yield:

2-((2S,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-yl)-isoindole-1,3-dione (136882-36-5,79528-50-0) → 3-Azidopropyl O-(3-O-benzyl-6-O-chloroacetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside (177421-34-0)

Guidance literature:

Multi-step reaction with 5 steps

1: p-TsOH*H₂O / acetonitrile / 16 h

2: 66 percent / NaH / dimethylformamide / 1.) r.t., 0.5 h, 2.) r.t., overnight

3: 58 percent / NIS, molecular sieves 4 Angstroem, triflic acid / CH₂Cl₂ / 1.) r.t., 1 h, 2.) -45 deg C, 1 h

4: 93 percent / 90percent CF₃COOH / CH₂Cl₂ / 1 h / 0 °C

5: 56 percent / 2,6-lutidine / CH₂Cl₂ / Ambient temperature

With 2,6-dimethylpyridine; N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; sodium hydride; toluene-4-sulfonic acid; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1080/07328309608005653

Reference yield:

phenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (79528-49-7) → 3-Azidopropyl O-(3-O-benzyl-6-O-chloroacetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside (177421-34-0)

Guidance literature:

Multi-step reaction with 6 steps

1: NaOMe / methanol / 1 h / Ambient temperature

2: p-TsOH*H₂O / acetonitrile / 16 h

3: 66 percent / NaH / dimethylformamide / 1.) r.t., 0.5 h, 2.) r.t., overnight

4: 58 percent / NIS, molecular sieves 4 Angstroem, triflic acid / CH₂Cl₂ / 1.) r.t., 1 h, 2.) -45 deg C, 1 h

5: 93 percent / 90percent CF₃COOH / CH₂Cl₂ / 1 h / 0 °C

6: 56 percent / 2,6-lutidine / CH₂Cl₂ / Ambient temperature

With 2,6-dimethylpyridine; N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; sodium methylate; sodium hydride; toluene-4-sulfonic acid; trifluoroacetic acid; In methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1080/07328309608005653

upstream raw materials:

3-Azidopropyl O-(3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside

Chloroacetic anhydride

2-((2S,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-yl)-isoindole-1,3-dione

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