p-methylphenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-1-thio-β-D-galactopyranoside

Base Information

• Chemical Name: p-methylphenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-1-thio-β-D-galactopyranoside
• CAS No.: 125760-21-6
• Molecular Formula: C₁₉H₂₃N₃O₇S
• Molecular Weight: 437.474
• Mol file: 125760-21-6.mol

Synonyms:p-methylphenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-1-thio-β-D-galactopyranoside

Chemical Property of p-methylphenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-1-thio-β-D-galactopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of p-methylphenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-1-thio-β-D-galactopyranoside

There total 1 articles about p-methylphenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-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: 51.0%

1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-D-galactopyranose (84278-00-2) + para-thiocresol (106-45-6) → p-methylphenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-1-thio-β-D-galactopyranoside (125760-21-6,501088-45-5) + p-methylphenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-1-thio-α-D-galactopyranoside (501088-45-5)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 0 - 20 ℃; for 24h;

DOI:10.1016/j.tetasy.2012.08.006

Reference yield:

p-methylphenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-1-thio-β-D-galactopyranoside (125760-21-6,501088-45-5) → C13H17N3O4S

Guidance literature:

With sodium methylate; In methanol; at 20 ℃; for 4h;

DOI:10.1016/j.tetasy.2012.08.006

Reference yield:

p-methylphenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-1-thio-β-D-galactopyranoside (125760-21-6,501088-45-5) → p-methoxyphenyl (2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl)-(1→3)-2-azido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside (1410786-23-0)

Guidance literature:

Multi-step reaction with 5 steps

1: sodium methylate / methanol / 4 h / 20 °C

2: toluene-4-sulfonic acid / 24 h / 20 °C

3: pyridine / 2 h / 20 °C

4: N-iodo-succinimide; perchloric acid adsorbed on silica gel / diethyl ether; dichloromethane / 1 h / -18 °C / Inert atmosphere; Molecular sieve

5: sodium methylate / methanol / 2 h / 20 °C

With pyridine; N-iodo-succinimide; perchloric acid adsorbed on silica gel; sodium methylate; toluene-4-sulfonic acid; In methanol; diethyl ether; dichloromethane;

DOI:10.1016/j.tetasy.2012.08.006

upstream raw materials:

1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-D-galactopyranose

para-thiocresol

Downstream raw materials:

p-methylphenyl 3-O-acetyl-2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-galactopyranoside

p-methoxyphenyl (3-O-acetyl-2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl)-(1→3)-2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranoside

p-methoxyphenyl (2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl)-(1→3)-2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranoside

p-methoxyphenyl (2-O-acetyl-3-O-benzyl-4,6-O-benzylidene-β-D-galactopyranosyl)-(1→3)-(2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl)-(1→3)-2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranoside