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

Base Information

• Chemical Name: 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
• CAS No.: 449177-43-9
• Molecular Formula: C₄₇H₄₅N₅O₁₅
• Molecular Weight: 919.899
• Mol file: 449177-43-9.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 5 articles about 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 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: 80.0%

6-O-p-methoxybenzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide (449177-35-9) + ethyl 3,4-di-O-acetyl-6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (449177-38-2) → 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)

Guidance literature:

With N-iodo-succinimide; 4 A molecular sieve; silver trifluoromethanesulfonate; In dichloromethane;

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) → 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)

Guidance literature:

Multi-step reaction with 4 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

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) → 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)

Guidance literature:

Multi-step reaction with 3 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

With N-iodo-succinimide; 3 A molecular sieve; 4 A molecular sieve; silver trifluoromethanesulfonate; sodium cyanoborohydride; toluene-4-sulfonic acid; 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:

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

ethyl 3,4-di-O-acetyl-6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

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