5-((Z)-(2-hydroxy-3-methoxybenzylidene))-3-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)-2-thioxo-4-thiazolidinone

Base Information

• Chemical Name: 5-((Z)-(2-hydroxy-3-methoxybenzylidene))-3-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)-2-thioxo-4-thiazolidinone
• CAS No.: 1352457-76-1
• Molecular Formula: C₂₅H₂₇NO₁₂S₂
• Molecular Weight: 597.621

Synonyms:5-((Z)-(2-hydroxy-3-methoxybenzylidene))-3-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)-2-thioxo-4-thiazolidinone

Chemical Property of 5-((Z)-(2-hydroxy-3-methoxybenzylidene))-3-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)-2-thioxo-4-thiazolidinone

Chemical Property:

Purity/Quality:

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Technology Process of 5-((Z)-(2-hydroxy-3-methoxybenzylidene))-3-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)-2-thioxo-4-thiazolidinone

There total 2 articles about 5-((Z)-(2-hydroxy-3-methoxybenzylidene))-3-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)-2-thioxo-4-thiazolidinone 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: 48.0%

5-((Z)-(2-hydroxy-3-methoxybenzylidene))-2-thioxo-4-thiazolidinone (99972-65-3) + 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside (3068-32-4) → C25H27NO12S2 (1352457-77-2) + 5-((Z)-(2-hydroxy-3-methoxybenzylidene))-3-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)-2-thioxo-4-thiazolidinone (1352457-76-1)

Guidance literature:

5-((Z)-(2-hydroxy-3-methoxybenzylidene))-2-thioxo-4-thiazolidinone; With sodium hydride; In acetonitrile; at 20 ℃; for 0.5h;

1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside; In acetonitrile; at 20 ℃; for 12h;

DOI:10.1016/j.carres.2011.09.035

Reference yield:

3-methoxy-2-hydroxybenzaldehyde (148-53-8) → C25H27NO12S2 (1352457-77-2) + 5-((Z)-(2-hydroxy-3-methoxybenzylidene))-3-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)-2-thioxo-4-thiazolidinone (1352457-76-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: piperidine / ethanol / 12 h

2.1: sodium hydride / acetonitrile / 0.5 h / 20 °C

2.2: 12 h / 20 °C

With piperidine; sodium hydride; In ethanol; acetonitrile;

DOI:10.1016/j.carres.2011.09.035

Reference yield: 78.0%

5-((Z)-(2-hydroxy-3-methoxybenzylidene))-3-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)-2-thioxo-4-thiazolidinone (1352457-76-1) → 5-((Z)-(2-hydroxy-3-methoxybenzylidene))-3-β-D-galactopyranosyl-2-thioxo-4-thiazolidinone (1352457-87-4)

Guidance literature:

With hydrogenchloride; water; In methanol; at 50 ℃; for 2h;

DOI:10.1016/j.carres.2011.09.035

upstream raw materials:

5-((Z)-(2-hydroxy-3-methoxybenzylidene))-2-thioxo-4-thiazolidinone

1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside

3-methoxy-2-hydroxybenzaldehyde

Downstream raw materials:

5-((Z)-(2-hydroxy-3-methoxybenzylidene))-3-β-D-galactopyranosyl-2-thioxo-4-thiazolidinone

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