2-(2,3,4-tri-O-acetyl-α-L-arabinopyranosyl)-6-[β-(4-methylphenyl)vinyl]-3-thioxo-2,3-dihydro-1,2,4-triazin-5(4H)-one

Base Information

• Chemical Name: 2-(2,3,4-tri-O-acetyl-α-L-arabinopyranosyl)-6-[β-(4-methylphenyl)vinyl]-3-thioxo-2,3-dihydro-1,2,4-triazin-5(4H)-one
• CAS No.: 674310-14-6
• Molecular Formula: C₂₃H₂₅N₃O₈S
• Molecular Weight: 503.533

Synonyms:2-(2,3,4-tri-O-acetyl-α-L-arabinopyranosyl)-6-[β-(4-methylphenyl)vinyl]-3-thioxo-2,3-dihydro-1,2,4-triazin-5(4H)-one

Chemical Property of 2-(2,3,4-tri-O-acetyl-α-L-arabinopyranosyl)-6-[β-(4-methylphenyl)vinyl]-3-thioxo-2,3-dihydro-1,2,4-triazin-5(4H)-one

Chemical Property:

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Technology Process of 2-(2,3,4-tri-O-acetyl-α-L-arabinopyranosyl)-6-[β-(4-methylphenyl)vinyl]-3-thioxo-2,3-dihydro-1,2,4-triazin-5(4H)-one

There total 4 articles about 2-(2,3,4-tri-O-acetyl-α-L-arabinopyranosyl)-6-[β-(4-methylphenyl)vinyl]-3-thioxo-2,3-dihydro-1,2,4-triazin-5(4H)-one 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: 77.0%

4-amino-2-(2,3,4-tri-O-acetyl-α-L-arabinopyranosyl)-6-[β-(4-methylphenyl)vinyl]-3-thioxo-2,3-dihydro-1,2,4-triazin-5(4H)-one (674309-86-5) → 2-(2,3,4-tri-O-acetyl-α-L-arabinopyranosyl)-6-[β-(4-methylphenyl)vinyl]-3-thioxo-2,3-dihydro-1,2,4-triazin-5(4H)-one (674310-14-6)

Guidance literature:

With acetic acid; sodium nitrite; In water; cooling;

DOI:10.1081/NCN-120023274

Reference yield:

4-benzylideneamino-2-(2,3,4-tri-O-acetyl-α-L-arabinopyranosyl)-6-[β-(4-methylphenyl)vinyl]-3-thioxo-2,3-dihydro-1,2,4-triazin-5(4H)-one → benzonitrile (100-47-0) + 2-(2,3,4-tri-O-acetyl-α-L-arabinopyranosyl)-6-[β-(4-methylphenyl)vinyl]-3-thioxo-2,3-dihydro-1,2,4-triazin-5(4H)-one (674310-14-6)

Guidance literature:

With benzaldehyde; for 0.5h; Heating;

DOI:10.1081/NCN-120023274

Reference yield:

2,3,4-tri-O-acetyl-α-L-arabinopyranosyl bromide (14227-90-8) → 2-(2,3,4-tri-O-acetyl-α-L-arabinopyranosyl)-6-[β-(4-methylphenyl)vinyl]-3-thioxo-2,3-dihydro-1,2,4-triazin-5(4H)-one (674310-14-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 77 percent / Et₃N / acetonitrile / 20 °C

2.1: 0.25 h / 150 - 160 °C

2.2: 78 percent / methanol / 0.5 h / Heating

3.1: PhCHO / 0.5 h / Heating

With benzaldehyde; triethylamine; In acetonitrile;

DOI:10.1081/NCN-120023274

upstream raw materials:

4-amino-2-(2,3,4-tri-O-acetyl-α-L-arabinopyranosyl)-6-[β-(4-methylphenyl)vinyl]-3-thioxo-2,3-dihydro-1,2,4-triazin-5(4H)-one

2,3,4-tri-O-acetyl-α-L-arabinopyranosyl bromide

4-amino-6-p-methylstyryl-2,3-dihydro-3-thioxo-1,2,4-triazin-5(4H)-one

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