phenyl 4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranoside

Base Information

• Chemical Name: phenyl 4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranoside
• CAS No.: 865096-53-3
• Molecular Formula: C₃₆H₃₃NO₈
• Molecular Weight: 607.66
• Mol file: 865096-53-3.mol

Synonyms:phenyl 4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranoside

Chemical Property of phenyl 4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenyl 4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranoside

There total 4 articles about phenyl 4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranoside 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: 68.0%

phenol (108-95-2,27073-41-2) + 4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranosyl fluoride (854911-48-1) → phenyl 4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranoside (865096-53-3)

Guidance literature:

With bis(cyclopentadienyl)hafnium dichloride; silver perchlorate; In dichloromethane; at -78 - -50 ℃; for 24h;

DOI:10.1016/j.carres.2005.06.010

Reference yield:

phenyl 3,6-di-O-benzyl-2-deoxy-4-O-methanesulfonyl-2-phthalimido-1-thio-β-D-glucopyranoside (865096-51-1) → phenyl 4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranoside (865096-53-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 70 percent / 18-crown-6 / dimethylformamide / 14 h / 140 °C

2: 65 percent / N-bromosuccinimide; diethylaminosulfur trifluoride / CH₂Cl₂ / 5.5 h / -15 - 0 °C

3: 68 percent / Cp₂HfCl₂; AgClO₄ / CH₂Cl₂ / 24 h / -78 - -50 °C

With N-Bromosuccinimide; bis(cyclopentadienyl)hafnium dichloride; diethylamino-sulfur trifluoride; silver perchlorate; 18-crown-6 ether; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.carres.2005.06.010

Reference yield:

phenyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (159734-70-0) → phenyl 4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranoside (865096-53-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 88 percent / pyridine / CH₂Cl₂ / 11 h / 40 °C

2: 70 percent / 18-crown-6 / dimethylformamide / 14 h / 140 °C

3: 65 percent / N-bromosuccinimide; diethylaminosulfur trifluoride / CH₂Cl₂ / 5.5 h / -15 - 0 °C

4: 68 percent / Cp₂HfCl₂; AgClO₄ / CH₂Cl₂ / 24 h / -78 - -50 °C

With pyridine; N-Bromosuccinimide; bis(cyclopentadienyl)hafnium dichloride; diethylamino-sulfur trifluoride; silver perchlorate; 18-crown-6 ether; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.carres.2005.06.010

upstream raw materials:

phenol

4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranosyl fluoride

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

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