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

Base Information

• Chemical Name: 4-(4-{[2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl]sulfonylmethyl}-1-H-1,2,3-triazol-1-yl)benzenesulfonamide
• CAS No.: 1159102-00-7
• Molecular Formula: C₂₃H₂₈N₄O₁₃S₂
• Molecular Weight: 632.626
• Mol file: 1159102-00-7.mol

Synonyms:4-(4-{[2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl]sulfonylmethyl}-1-H-1,2,3-triazol-1-yl)benzenesulfonamide

Chemical Property of 4-(4-{[2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl]sulfonylmethyl}-1-H-1,2,3-triazol-1-yl)benzenesulfonamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-(4-{[2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl]sulfonylmethyl}-1-H-1,2,3-triazol-1-yl)benzenesulfonamide

There total 6 articles about 4-(4-{[2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl]sulfonylmethyl}-1-H-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: 83.0%

4-(4-{[2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl]thiomethyl}-1-H-1,2,3-triazol-1-yl)benzenesulfonamide (1159101-98-0) → 4-(4-{[2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl]sulfonylmethyl}-1-H-1,2,3-triazol-1-yl)benzenesulfonamide (1159102-00-7)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 20 ℃; for 2h;

DOI:10.1021/jm200892s

Reference yield: 63.0%

2,3,4,6-tetra-O-acetyl-β-D-sulfonylpropynylglucopyranoside (1159101-95-7) + 4-azidobenzenesulfonamide (36326-86-0) → 4-(4-{[2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl]sulfonylmethyl}-1-H-1,2,3-triazol-1-yl)benzenesulfonamide (1159102-00-7)

Guidance literature:

With copper(ll) sulfate pentahydrate; sodium L-ascorbate; In ethanol; water; at 40 ℃; for 2h;

DOI:10.1016/j.bmcl.2009.02.086

Reference yield:

4-azidobenzenesulfonamide (36326-86-0) → 4-(4-{[2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl]sulfonylmethyl}-1-H-1,2,3-triazol-1-yl)benzenesulfonamide (1159102-00-7)

Guidance literature:

Multi-step reaction with 2 steps

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

2: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 0 - 20 °C

With N-Bromosuccinimide; copper(l) iodide; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jm200892s

upstream raw materials:

2,3,4,6-tetra-O-acetyl-β-D-sulfonylpropynylglucopyranoside

4-azidobenzenesulfonamide

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

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

Downstream raw materials:

4-(4-{[β-D-glucopyranosyl]sulfonylmethyl}-1-H-1,2,3-triazol-1-yl)benzenesulfonamide