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

Base Information

• Chemical Name: phenyl 4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-galactopyranoside
• CAS No.: 865096-52-2
• Molecular Formula: C₃₆H₃₃NO₇S
• Molecular Weight: 623.727
• Mol file: 865096-52-2.mol

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

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

There total 2 articles about phenyl 4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-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: 70.0%

phenyl 3,6-di-O-benzyl-2-deoxy-4-O-methanesulfonyl-2-phthalimido-1-thio-β-D-glucopyranoside (865096-51-1) + potassium acetate (127-08-2) → phenyl 4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-galactopyranoside (865096-52-2)

Guidance literature:

18-crown-6 ether; In N,N-dimethyl-formamide; at 140 ℃; for 14h;

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-1-thio-β-D-galactopyranoside (865096-52-2)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With pyridine; 18-crown-6 ether; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.carres.2005.06.010

Reference yield: 97.0%

phenyl 4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-galactopyranoside (865096-52-2) + benzyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-beta-D-glucopyranoside (80035-36-5) → C65H60N2O14

Guidance literature:

With N-iodo-succinimide; trifluorormethanesulfonic acid; In dichloromethane; at -20 ℃; for 1h; Molecular sieve; Inert atmosphere;

DOI:10.1002/anie.201600488

upstream raw materials:

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

potassium acetate

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

Downstream raw materials:

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

phenyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-galactopyranoside

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