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

Base Information

• Chemical Name: O-(3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide
• CAS No.: 344597-15-5
• Molecular Formula: C₅₆H₄₉N₅O₁₂
• Molecular Weight: 984.031
• Mol file: 344597-15-5.mol

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

Chemical Property of O-(3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->4)-3,6-di-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 O-(3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide

There total 10 articles about O-(3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->4)-3,6-di-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: 85.0%

3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide (161315-66-8) + phenyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (208644-70-6) → O-(3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide (344597-15-5)

Guidance literature:

phenyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside; With 1,1'-sulfinylbisbenzene; 4 A molecular sieve; In dichloromethane; for 0.5h;

With trifluoromethanesulfonic acid anhydride; In dichloromethane; at -60 ℃; for 0.25h;

3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide; In dichloromethane; at -60 - 0 ℃; for 4h; Further stages.;

DOI:10.1039/b711531h

Reference yield: 81.0%

3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide (161315-66-8) + 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl fluoride (277310-81-3) → O-(3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide (344597-15-5)

Guidance literature:

With bis(cyclopentadienyl)hafnium dichloride; silver perchlorate; In dichloromethane;

DOI:10.1016/S0040-4039(01)00342-2

Reference yield:

1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose (10022-13-6) → O-(3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide (344597-15-5)

Guidance literature:

Multi-step reaction with 8 steps

1: NH₂NH₂; AcOH / dimethylformamide

2: imidazole; 4-dimethylaminopyridine / dimethylformamide

3: t-BuOK / methanol; tetrahydrofuran

4: camphorsulfonic acid / acetonitrile

5: NaH / dimethylformamide

6: tetrabutylammonium fluoride; AcOH / tetrahydrofuran

7: dimethylaminosulfur trifluoride / tetrahydrofuran

8: 81 percent / Cp₂HfCl₂; AgClO₄ / CH₂Cl₂

With 1H-imidazole; dmap; bis(cyclopentadienyl)hafnium dichloride; dimethylaminosulphur trifluoride; camphor-10-sulfonic acid; potassium tert-butylate; tetrabutyl ammonium fluoride; silver perchlorate; sodium hydride; acetic acid; hydrazine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0040-4039(01)00342-2

upstream raw materials:

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

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

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

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

Downstream raw materials:

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

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

N-[3-acetylamino-5-(7-acetylamino-8-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-4-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl]-2-tert-butoxycarbonylamino-succinamic acid allyl ester