(5Z)-5-benzylidene-2-sulfanylidene-3-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-1,3-thiazolidin-4-one

Base Information

• Chemical Name: (5Z)-5-benzylidene-2-sulfanylidene-3-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-1,3-thiazolidin-4-one
• CAS No.: 65562-43-8
• Molecular Formula: C₁₆H₁₇NO₆S₂
• Molecular Weight: 383.446
• NSC Number: 284178
• DSSTox Substance ID: DTXSID30420414

Synonyms:NSC284178;65562-43-8;DTXSID30420414;NSC-284178

Chemical Property of (5Z)-5-benzylidene-2-sulfanylidene-3-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-1,3-thiazolidin-4-one

Chemical Property:

• Vapor Pressure: 1.23E-16mmHg at 25°C
• Boiling Point: 628°C at 760 mmHg
• Flash Point: 333.6°C
• Density: 1.66g/cm³
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 3
• Exact Mass: 383.04972961
• Heavy Atom Count: 25
• Complexity: 565

Purity/Quality:

85.0-99.8% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C=C2C(=O)N(C(=S)S2)C3C(C(C(C(O3)CO)O)O)O
• Isomeric SMILES: C1=CC=C(C=C1)/C=C\2/C(=O)N(C(=S)S2)C3C(C(C(C(O3)CO)O)O)O

Technology Process of (5Z)-5-benzylidene-2-sulfanylidene-3-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-1,3-thiazolidin-4-one

There total 3 articles about (5Z)-5-benzylidene-2-sulfanylidene-3-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-1,3-thiazolidin-4-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:

N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-5-(3,4-dimethoxybenzylidene)rhodanine (65562-18-7) → 5-benzylidene-3-β-D-glucopyranosyl-2-thioxo-thiazolidin-4-one (65562-43-8)

Guidance literature:

With hydrogenchloride; In methanol; Ambient temperature;

DOI:10.1002/jps.2600661126

Reference yield:

5-benzylidene-2-thioxothiazolidin-4-one (3806-42-6,174813-24-2) → 5-benzylidene-3-β-D-glucopyranosyl-2-thioxo-thiazolidin-4-one (65562-43-8)

Guidance literature:

Multi-step reaction with 2 steps

1: aq. NaOH / acetone; tetrahydrofuran / Ambient temperature

2: aq. HCl / methanol / Ambient temperature

With hydrogenchloride; sodium hydroxide; In tetrahydrofuran; methanol; acetone;

DOI:10.1002/jps.2600661126

Reference yield:

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → 5-benzylidene-3-β-D-glucopyranosyl-2-thioxo-thiazolidin-4-one (65562-43-8)

Guidance literature:

Multi-step reaction with 2 steps

1: aq. NaOH / acetone; tetrahydrofuran / Ambient temperature

2: aq. HCl / methanol / Ambient temperature

With hydrogenchloride; sodium hydroxide; In tetrahydrofuran; methanol; acetone;

DOI:10.1002/jps.2600661126

upstream raw materials:

N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-5-(3,4-dimethoxybenzylidene)rhodanine

5-benzylidene-2-thioxothiazolidin-4-one

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

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