6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->4)-6-O-p-methoxybenzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide

Base Information

• Chemical Name: 6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->4)-6-O-p-methoxybenzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide
• CAS No.: 449177-45-1
• Molecular Formula: C₄₃H₄₁N₅O₁₃
• Molecular Weight: 835.824
• Mol file: 449177-45-1.mol

Synonyms:6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->4)-6-O-p-methoxybenzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide

Chemical Property of 6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->4)-6-O-p-methoxybenzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->4)-6-O-p-methoxybenzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide

There total 7 articles about 6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->4)-6-O-p-methoxybenzyl-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: 90.0%

acetic acid 3-acetoxy-6-[6-azido-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-4-hydroxy-2-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-yloxy]-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-4-yl ester (449177-43-9) → 6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->4)-6-O-p-methoxybenzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide (449177-45-1)

Guidance literature:

With guanidinium nitrate; guanidine nitrate; In dichloromethane; for 1h;

DOI:10.1002/1099-0690(200205)2002:10<1614::AID-EJOC1614>3.0.CO;2-1

Reference yield:

3,4,6-tri-O-acetyl-2-deoxy-2-N-phthalimido-β-D-glucopyranosyl azide (102816-24-0) → 6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->4)-6-O-p-methoxybenzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide (449177-45-1)

Guidance literature:

Multi-step reaction with 5 steps

1: guanidine; guanidinium nitrate / methanol / 20 °C

2: p-TsOH / acetonitrile / 0.5 h / 50 °C

3: 61 percent / NaCNBH₃; TFA; 3 Angstroem molecular sieves / dimethylformamide / 18 h / 20 °C

4: 80 percent / 4 Angstroem molecular sieves; NIS; AgOTf / CH₂Cl₂

5: 90 percent / guanidine; guanidinium nitrate / CH₂Cl₂ / 1 h

With N-iodo-succinimide; guanidinium nitrate; 3 A molecular sieve; 4 A molecular sieve; silver trifluoromethanesulfonate; sodium cyanoborohydride; toluene-4-sulfonic acid; guanidine nitrate; trifluoroacetic acid; In methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1002/1099-0690(200205)2002:10<1614::AID-EJOC1614>3.0.CO;2-1

Reference yield:

2-deoxy-2-phthalimido-β-D-glucopyranosyl azide (102816-23-9) → 6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->4)-6-O-p-methoxybenzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide (449177-45-1)

Guidance literature:

Multi-step reaction with 4 steps

1: p-TsOH / acetonitrile / 0.5 h / 50 °C

2: 61 percent / NaCNBH₃; TFA; 3 Angstroem molecular sieves / dimethylformamide / 18 h / 20 °C

3: 80 percent / 4 Angstroem molecular sieves; NIS; AgOTf / CH₂Cl₂

4: 90 percent / guanidine; guanidinium nitrate / CH₂Cl₂ / 1 h

With N-iodo-succinimide; guanidinium nitrate; 3 A molecular sieve; 4 A molecular sieve; silver trifluoromethanesulfonate; sodium cyanoborohydride; toluene-4-sulfonic acid; guanidine nitrate; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1002/1099-0690(200205)2002:10<1614::AID-EJOC1614>3.0.CO;2-1

upstream raw materials:

acetic acid 3-acetoxy-6-[6-azido-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-4-hydroxy-2-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-yloxy]-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-4-yl ester

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

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

ethyl 6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

Downstream raw materials:

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