methyl 2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl-(1->3)-4-O-acetyl-2,6-di-O-benzoyl-β-D-galactopyranosyl-(1->4)-6-O-acetyl-3-O-benzyl-2-deoxy-2-azido-β-D-glucopyranoside

Base Information

• Chemical Name: methyl 2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl-(1->3)-4-O-acetyl-2,6-di-O-benzoyl-β-D-galactopyranosyl-(1->4)-6-O-acetyl-3-O-benzyl-2-deoxy-2-azido-β-D-glucopyranoside
• CAS No.: 865860-11-3
• Molecular Formula: C₅₂H₅₉N₃O₂₃
• Molecular Weight: 1094.05
• Mol file: 865860-11-3.mol

Synonyms:methyl 2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl-(1->3)-4-O-acetyl-2,6-di-O-benzoyl-β-D-galactopyranosyl-(1->4)-6-O-acetyl-3-O-benzyl-2-deoxy-2-azido-β-D-glucopyranoside

Chemical Property of methyl 2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl-(1->3)-4-O-acetyl-2,6-di-O-benzoyl-β-D-galactopyranosyl-(1->4)-6-O-acetyl-3-O-benzyl-2-deoxy-2-azido-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl-(1->3)-4-O-acetyl-2,6-di-O-benzoyl-β-D-galactopyranosyl-(1->4)-6-O-acetyl-3-O-benzyl-2-deoxy-2-azido-β-D-glucopyranoside

There total 5 articles about methyl 2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl-(1->3)-4-O-acetyl-2,6-di-O-benzoyl-β-D-galactopyranosyl-(1->4)-6-O-acetyl-3-O-benzyl-2-deoxy-2-azido-β-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: 95.0%

methyl 3,4,6-tri-O-acetyl-2-O-{(1S)-phenyl-2-(phenylsulfanyl)ethyl}-α-D-galactopyranosyl-(1->3)-2,6-di-O-benzoyl-β-D-galactopyranosyl-(1->4)-6-O-acetyl-3-O-benzyl-2-deoxy-2-azido-β-D-glucopyranoside (865860-10-2) + acetic anhydride (108-24-7) → methyl 2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl-(1->3)-4-O-acetyl-2,6-di-O-benzoyl-β-D-galactopyranosyl-(1->4)-6-O-acetyl-3-O-benzyl-2-deoxy-2-azido-β-D-glucopyranoside (865860-11-3)

Guidance literature:

With boron trifluoride diethyl etherate; at 0 ℃; for 0.666667h;

DOI:10.1021/ja052548h

Reference yield:

3,4,6-tri-O-acetyl-2-O-{(1S)-phenyl-2-(phenylsulfanyl)ethyl}-D-galactopyranose → methyl 2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl-(1->3)-4-O-acetyl-2,6-di-O-benzoyl-β-D-galactopyranosyl-(1->4)-6-O-acetyl-3-O-benzyl-2-deoxy-2-azido-β-D-glucopyranoside (865860-11-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 91 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 1 h / 0 °C

2.1: trimethylsilyl trifluoromethanesulfonate; molecular sieves 4 Angstroem / CH₂Cl₂ / 0.08 h / 0 °C

2.2: CH₂Cl₂ / 4 h / 0 - 20 °C

3.1: 63 mg / N-iodosuccinimide / CH₂Cl₂ / 2 h / -78 - 20 °C

4.1: 95 percent / BF₃*OEt₂ / 0.67 h / 0 °C

With N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; boron trifluoride diethyl etherate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane;

DOI:10.1021/ja052548h

Reference yield:

acetyl 3,4,6-tri-O-acetyl-2-O-{(1S)-phenyl-2-(phenylsulfanyl)ethyl}-α-D-galactopyranose (865860-12-4) → methyl 2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl-(1->3)-4-O-acetyl-2,6-di-O-benzoyl-β-D-galactopyranosyl-(1->4)-6-O-acetyl-3-O-benzyl-2-deoxy-2-azido-β-D-glucopyranoside (865860-11-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 93 percent / hydrazinium acetate / dimethylformamide / 20 °C

2.1: 91 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 1 h / 0 °C

3.1: trimethylsilyl trifluoromethanesulfonate; molecular sieves 4 Angstroem / CH₂Cl₂ / 0.08 h / 0 °C

3.2: CH₂Cl₂ / 4 h / 0 - 20 °C

4.1: 63 mg / N-iodosuccinimide / CH₂Cl₂ / 2 h / -78 - 20 °C

5.1: 95 percent / BF₃*OEt₂ / 0.67 h / 0 °C

With N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; boron trifluoride diethyl etherate; hydrazinium monoacetate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja052548h

upstream raw materials:

methyl 3,4,6-tri-O-acetyl-2-O-{(1S)-phenyl-2-(phenylsulfanyl)ethyl}-α-D-galactopyranosyl-(1->3)-2,6-di-O-benzoyl-β-D-galactopyranosyl-(1->4)-6-O-acetyl-3-O-benzyl-2-deoxy-2-azido-β-D-glucopyranoside

acetic anhydride

acetyl 3,4,6-tri-O-acetyl-2-O-{(1S)-phenyl-2-(phenylsulfanyl)ethyl}-α-D-galactopyranose

3,4,6-tri-O-acetyl-2-O-{(1S)-phenyl-2-(phenylsulfanyl)ethyl}-α-D-galactopyranosyl trichloroacetimidate