benzyl O-(3,6-di-O-acetyl-2-azido-4-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-O-(methyl 2-O-acetyl-3-O-benzyl-α-L-idopyranosyluronate)-(1->4)-6-O-acetyl-3-O-benzyl-2-(benzyloxycarbonyl)amino-2-deoxy-α-D-glucopyranoside

Base Information

• Chemical Name: benzyl O-(3,6-di-O-acetyl-2-azido-4-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-O-(methyl 2-O-acetyl-3-O-benzyl-α-L-idopyranosyluronate)-(1->4)-6-O-acetyl-3-O-benzyl-2-(benzyloxycarbonyl)amino-2-deoxy-α-D-glucopyranoside
• CAS No.: 87907-39-9
• Molecular Formula: C₆₃H₇₀N₄O₂₁
• Molecular Weight: 1219.26
• Mol file: 87907-39-9.mol

Synonyms:benzyl O-(3,6-di-O-acetyl-2-azido-4-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-O-(methyl 2-O-acetyl-3-O-benzyl-α-L-idopyranosyluronate)-(1->4)-6-O-acetyl-3-O-benzyl-2-(benzyloxycarbonyl)amino-2-deoxy-α-D-glucopyranoside

Chemical Property of benzyl O-(3,6-di-O-acetyl-2-azido-4-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-O-(methyl 2-O-acetyl-3-O-benzyl-α-L-idopyranosyluronate)-(1->4)-6-O-acetyl-3-O-benzyl-2-(benzyloxycarbonyl)amino-2-deoxy-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl O-(3,6-di-O-acetyl-2-azido-4-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-O-(methyl 2-O-acetyl-3-O-benzyl-α-L-idopyranosyluronate)-(1->4)-6-O-acetyl-3-O-benzyl-2-(benzyloxycarbonyl)amino-2-deoxy-α-D-glucopyranoside

There total 6 articles about benzyl O-(3,6-di-O-acetyl-2-azido-4-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-O-(methyl 2-O-acetyl-3-O-benzyl-α-L-idopyranosyluronate)-(1->4)-6-O-acetyl-3-O-benzyl-2-(benzyloxycarbonyl)amino-2-deoxy-α-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: 88.0%

3,6-di-O-acetyl-2-azido-4-O-benzyl-2-deoxy-α-D-glucopyranosyl bromide (67546-24-1) + benzyl 6-O-acetyl-3-O-benzyl-2-<(benzyloxycarbonyl)amino>-2-deoxy-4-O-(methyl 2-O-acetyl-3-O-benzyl-α-L-idopyranosyluronate)-α-D-glucopyranoside (87907-11-7) → benzyl O-(3,6-di-O-acetyl-2-azido-4-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-O-(methyl 2-O-acetyl-3-O-benzyl-α-L-idopyranosyluronate)-(1->4)-6-O-acetyl-3-O-benzyl-2-(benzyloxycarbonyl)amino-2-deoxy-α-D-glucopyranoside (87907-39-9)

Guidance literature:

With 2,4,6-trimethyl-pyridine; 4 A molecular sieve; silver trifluoromethanesulfonate; In dichloromethane; at -20 ℃; for 2h; in the dark;

DOI:10.1016/0008-6215(84)85281-7

Reference yield:

methyl (2,4-di-O-acetyl-3-O-benzyl-α-L-idopyranosyl bromide)uronate (87327-03-5) → benzyl O-(3,6-di-O-acetyl-2-azido-4-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-O-(methyl 2-O-acetyl-3-O-benzyl-α-L-idopyranosyluronate)-(1->4)-6-O-acetyl-3-O-benzyl-2-(benzyloxycarbonyl)amino-2-deoxy-α-D-glucopyranoside (87907-39-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 73 percent / 2,4,6-trimethylpyridine / CH₂Cl₂ / 15 h / Ambient temperature

2: 1.) methanol, K₂CO₃, 2.) pyridine / 1.) -20 deg C, 5 h, 2.) dichloromethane, -20 deg C, 30 min

3: 35 percent / 0.2 M 2,6-dimethylpyridinium perchlorate / chlorobenzene / 1.5 h / Heating

4: 86 percent / thiourea, ethanol / pyridine / 0.5 h / 100 °C

5: 88 percent / 4 A molecular sieve, 2,4,6-trimethylpyridine, silver triflate / CH₂Cl₂ / 2 h / -20 °C / in the dark

With pyridine; 2,4,6-trimethyl-pyridine; methanol; ethanol; 4 A molecular sieve; silver trifluoromethanesulfonate; 2,6-lutidinium perchlorate; potassium carbonate; thiourea; In pyridine; dichloromethane; chlorobenzene;

DOI:10.1016/0008-6215(84)85281-7

Reference yield:

methyl 4-O-acetyl-3-O-benzyl-β-L-idopyranuronate 1,2-(tert-butyl orthoacetate) (87326-82-7) → benzyl O-(3,6-di-O-acetyl-2-azido-4-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-O-(methyl 2-O-acetyl-3-O-benzyl-α-L-idopyranosyluronate)-(1->4)-6-O-acetyl-3-O-benzyl-2-(benzyloxycarbonyl)amino-2-deoxy-α-D-glucopyranoside (87907-39-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) methanol, K₂CO₃, 2.) pyridine / 1.) -20 deg C, 5 h, 2.) dichloromethane, -20 deg C, 30 min

2: 35 percent / 0.2 M 2,6-dimethylpyridinium perchlorate / chlorobenzene / 1.5 h / Heating

3: 86 percent / thiourea, ethanol / pyridine / 0.5 h / 100 °C

4: 88 percent / 4 A molecular sieve, 2,4,6-trimethylpyridine, silver triflate / CH₂Cl₂ / 2 h / -20 °C / in the dark

With pyridine; 2,4,6-trimethyl-pyridine; methanol; ethanol; 4 A molecular sieve; silver trifluoromethanesulfonate; 2,6-lutidinium perchlorate; potassium carbonate; thiourea; In pyridine; dichloromethane; chlorobenzene;

DOI:10.1016/0008-6215(84)85281-7

upstream raw materials:

3,6-di-O-acetyl-2-azido-4-O-benzyl-2-deoxy-α-D-glucopyranosyl bromide

benzyl 6-O-acetyl-3-O-benzyl-2-<(benzyloxycarbonyl)amino>-2-deoxy-4-O-(methyl 2-O-acetyl-3-O-benzyl-α-L-idopyranosyluronate)-α-D-glucopyranoside

methyl (2,4-di-O-acetyl-3-O-benzyl-α-L-idopyranosyl bromide)uronate

methyl 4-O-acetyl-3-O-benzyl-β-L-idopyranuronate 1,2-(tert-butyl orthoacetate)

Downstream raw materials:

benzyl O-(2-azido-4-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-O-(methyl 3-O-benzyl-α-L-idopyranosyluronate)-(1->4)-3-O-benzyl-2-(benzyloxycarbonyl)amino-2-deoxy-α-D-glucopyranoside