6-O-p-methoxybenzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide

Base Information

• Chemical Name: 6-O-p-methoxybenzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide
• CAS No.: 449177-35-9
• Molecular Formula: C₂₂H₂₂N₄O₇
• Molecular Weight: 454.439
• Mol file: 449177-35-9.mol

Synonyms:6-O-p-methoxybenzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide

Chemical Property of 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-p-methoxybenzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide

There total 3 articles about 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: 61.0%

2-[(2R,4aR,6R,7R,8R,8aS)-6-Azido-8-hydroxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-isoindole-1,3-dione (449177-33-7) → 6-O-p-methoxybenzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide (449177-35-9)

Guidance literature:

With 3 A molecular sieve; sodium cyanoborohydride; trifluoroacetic acid; In N,N-dimethyl-formamide; at 20 ℃; for 18h;

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-p-methoxybenzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide (449177-35-9)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With 3 A molecular sieve; sodium cyanoborohydride; toluene-4-sulfonic acid; trifluoroacetic acid; In N,N-dimethyl-formamide; acetonitrile;

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-p-methoxybenzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide (449177-35-9)

Guidance literature:

Multi-step reaction with 3 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

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

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

upstream raw materials:

2-[(2R,4aR,6R,7R,8R,8aS)-6-Azido-8-hydroxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-isoindole-1,3-dione

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

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

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

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

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