phenyl 6-O-acetyl-4-(N-benzyloxycarbonyl)-amino-2-azido-3-O-benzyl-2,4-dideoxy-1-thio-β-D-galactopyranoside

Base Information

• Chemical Name: phenyl 6-O-acetyl-4-(N-benzyloxycarbonyl)-amino-2-azido-3-O-benzyl-2,4-dideoxy-1-thio-β-D-galactopyranoside
• CAS No.: 666753-87-3
• Molecular Formula: C₂₉H₃₀N₄O₆S
• Molecular Weight: 562.646
• Mol file: 666753-87-3.mol

Synonyms:phenyl 6-O-acetyl-4-(N-benzyloxycarbonyl)-amino-2-azido-3-O-benzyl-2,4-dideoxy-1-thio-β-D-galactopyranoside

Chemical Property of phenyl 6-O-acetyl-4-(N-benzyloxycarbonyl)-amino-2-azido-3-O-benzyl-2,4-dideoxy-1-thio-β-D-galactopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenyl 6-O-acetyl-4-(N-benzyloxycarbonyl)-amino-2-azido-3-O-benzyl-2,4-dideoxy-1-thio-β-D-galactopyranoside

There total 7 articles about phenyl 6-O-acetyl-4-(N-benzyloxycarbonyl)-amino-2-azido-3-O-benzyl-2,4-dideoxy-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: 100.0%

acetic anhydride (108-24-7) + phenyl 4-(N-benzyloxycarbonyl)-amino-2-azido-3-O-benzyl-2,4-dideoxy-1-thio-β-D-galactopyranoside (666753-86-2) → phenyl 6-O-acetyl-4-(N-benzyloxycarbonyl)-amino-2-azido-3-O-benzyl-2,4-dideoxy-1-thio-β-D-galactopyranoside (666753-87-3)

Guidance literature:

With pyridine; at 20 ℃; for 2h;

DOI:10.1039/b309823k

Reference yield:

N-(Benzyloxycarbonyloxy)succinimide (13139-17-8) → phenyl 6-O-acetyl-4-(N-benzyloxycarbonyl)-amino-2-azido-3-O-benzyl-2,4-dideoxy-1-thio-β-D-galactopyranoside (666753-87-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 844 mg / Et₃N / CH₂Cl₂ / 8 h / 20 °C

2: 100 percent / pyridine / 2 h / 20 °C

With pyridine; triethylamine; In dichloromethane;

DOI:10.1039/b309823k

Reference yield:

phenyl 2-azido-3-O-benzyl-2-deoxy-1-thio-β-D-glucopyranoside (666753-83-9) → phenyl 6-O-acetyl-4-(N-benzyloxycarbonyl)-amino-2-azido-3-O-benzyl-2,4-dideoxy-1-thio-β-D-galactopyranoside (666753-87-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 0.75 h / 0 °C

2: pyridine / CH₂Cl₂ / 0.08 h / 0 °C

3: 4.16 g / (i-Pr)2NEt / CH₂Cl₂ / 3.5 h / 0 °C

4: aq. AcOH / 0.5 h / 20 °C

5: 844 mg / Et₃N / CH₂Cl₂ / 8 h / 20 °C

6: 100 percent / pyridine / 2 h / 20 °C

With pyridine; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; In dichloromethane;

DOI:10.1039/b309823k

upstream raw materials:

acetic anhydride

phenyl 4-(N-benzyloxycarbonyl)-amino-2-azido-3-O-benzyl-2,4-dideoxy-1-thio-β-D-galactopyranoside

N-(Benzyloxycarbonyloxy)succinimide

phenyl 2-azido-3-O-benzyl-2-deoxy-1-thio-β-D-glucopyranoside