methyl 2-S-(2-nitrophenyl)-3,4,5-tri-O-acetyl-α-D-arabino-2-hexulopyranosonate

Base Information

• Chemical Name: methyl 2-S-(2-nitrophenyl)-3,4,5-tri-O-acetyl-α-D-arabino-2-hexulopyranosonate
• CAS No.: 225794-00-3
• Molecular Formula: C₁₉H₂₁NO₁₁S
• Molecular Weight: 471.442
• Mol file: 225794-00-3.mol

Synonyms:methyl 2-S-(2-nitrophenyl)-3,4,5-tri-O-acetyl-α-D-arabino-2-hexulopyranosonate

Chemical Property of methyl 2-S-(2-nitrophenyl)-3,4,5-tri-O-acetyl-α-D-arabino-2-hexulopyranosonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2-S-(2-nitrophenyl)-3,4,5-tri-O-acetyl-α-D-arabino-2-hexulopyranosonate

There total 3 articles about methyl 2-S-(2-nitrophenyl)-3,4,5-tri-O-acetyl-α-D-arabino-2-hexulopyranosonate 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: 92.0%

o-nitrothiophenol (4875-10-9) + methyl (3,4,5-tri-O-acetyl-β-D-arabino-hex-2-ulopyranosyl)onate bromide (225937-33-7) → methyl 2-S-(2-nitrophenyl)-3,4,5-tri-O-acetyl-α-D-arabino-2-hexulopyranosonate (225794-00-3)

Guidance literature:

With potassium carbonate; In acetone; for 2h; Heating;

DOI:10.1002/jhet.5570360220

Reference yield:

methyl β-D-arabino-hex-2-ulopyranosonate (72933-34-7) → methyl 2-S-(2-nitrophenyl)-3,4,5-tri-O-acetyl-α-D-arabino-2-hexulopyranosonate (225794-00-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 78 percent / conc. H₂SO₄ / 0.33 h / 60 °C

2: 98 percent / HBr, glacial AcOH / 2 h / 20 °C

3: 92 percent / K₂CO₃ / acetone / 2 h / Heating

With sulfuric acid; hydrogen bromide; potassium carbonate; acetic acid; In acetone;

DOI:10.1002/jhet.5570360220

Reference yield:

methyl 2,3,4,5-tetra-O-acetyl-β-D-arabino-hex-2-ulopyranosonate (225793-99-7) → methyl 2-S-(2-nitrophenyl)-3,4,5-tri-O-acetyl-α-D-arabino-2-hexulopyranosonate (225794-00-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / HBr, glacial AcOH / 2 h / 20 °C

2: 92 percent / K₂CO₃ / acetone / 2 h / Heating

With hydrogen bromide; potassium carbonate; acetic acid; In acetone;

DOI:10.1002/jhet.5570360220

upstream raw materials:

o-nitrothiophenol

methyl (3,4,5-tri-O-acetyl-β-D-arabino-hex-2-ulopyranosyl)onate bromide

methyl β-D-arabino-hex-2-ulopyranosonate

methyl 2,3,4,5-tetra-O-acetyl-β-D-arabino-hex-2-ulopyranosonate

Downstream raw materials:

methyl 2-S-(2-aminophenyl)-3,4,5-tri-O-acetyl-α-D-arabino-2-hexulopyranosonate