p-(4-{[2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl]thiomethyl}-5-iodo-1H-1,2,3-triazol-1-yl)benzenesulfonamide

Base Information

• Chemical Name: p-(4-{[2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl]thiomethyl}-5-iodo-1H-1,2,3-triazol-1-yl)benzenesulfonamide
• CAS No.: 1333497-86-1
• Molecular Formula: C₂₃H₂₇IN₄O₁₁S₂
• Molecular Weight: 726.524
• Mol file: 1333497-86-1.mol

Synonyms:p-(4-{[2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl]thiomethyl}-5-iodo-1H-1,2,3-triazol-1-yl)benzenesulfonamide

Chemical Property of p-(4-{[2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl]thiomethyl}-5-iodo-1H-1,2,3-triazol-1-yl)benzenesulfonamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of p-(4-{[2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl]thiomethyl}-5-iodo-1H-1,2,3-triazol-1-yl)benzenesulfonamide

There total 2 articles about p-(4-{[2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl]thiomethyl}-5-iodo-1H-1,2,3-triazol-1-yl)benzenesulfonamide 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: 45.0%

4-azidobenzenesulfonamide (36326-86-0) + 2,3,4,6-tetra-O-acetyl-S-(prop-2-ynyl)-1-thio-β-D-galactopyranoside (266364-02-7) → 4-(4-{[2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl]thiomethyl}-1-H-1,2,3-triazol-1-yl)benzenesulfonamide (1159102-01-8) + p-(4-{[2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl]thiomethyl}-5-iodo-1H-1,2,3-triazol-1-yl)benzenesulfonamide (1333497-86-1)

Guidance literature:

With N-Bromosuccinimide; copper(l) iodide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 20 ℃;

DOI:10.1021/jm200892s

Reference yield:

β-D-galactose peracetate (4163-60-4) → p-(4-{[2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl]thiomethyl}-5-iodo-1H-1,2,3-triazol-1-yl)benzenesulfonamide (1333497-86-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: boron trifluoride diethyl etherate; thiourea / acetonitrile / 1 h / Reflux

1.2: 4 h / 20 °C

2.1: N-Bromosuccinimide; copper(l) iodide; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 20 °C

With N-Bromosuccinimide; copper(l) iodide; boron trifluoride diethyl etherate; N-ethyl-N,N-diisopropylamine; thiourea; In tetrahydrofuran; acetonitrile;

DOI:10.1021/jm200892s

Reference yield: 91.0%

p-(4-{[2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl]thiomethyl}-5-iodo-1H-1,2,3-triazol-1-yl)benzenesulfonamide (1333497-86-1) → p-(4-{(β-D-galactopyranosyl)thiomethyl}-5-iodo-1H-1,2,3-triazol-1-yl)benzenesulfonamide (1333497-94-1)

Guidance literature:

With methanol; sodium methylate; at 0 - 20 ℃;

DOI:10.1021/jm200892s

upstream raw materials:

4-azidobenzenesulfonamide

2,3,4,6-tetra-O-acetyl-S-(prop-2-ynyl)-1-thio-β-D-galactopyranoside

β-D-galactose peracetate

Downstream raw materials:

p-(4-{[2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl]sulfonylmethyl}-5-iodo-1H-1,2,3-triazol-1-yl)benzenesulfonamide

p-(4-{(β-D-galactopyranosyl)thiomethyl}-5-iodo-1H-1,2,3-triazol-1-yl)benzenesulfonamide

p-(4-{[β-D-galactopyranosyl]sulfonylmethyl}-5-iodo-1H-1,2,3-triazol-1-yl)benzenesulfonamide

p-(4-{[2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl]thiomethyl}-5-(3-hydroxyprop-1-ynyl)-1H-1,2,3-triazol-1-yl)benzenesulfonamide