(2S,5S)-thiolane-2,5-dicarboxylic acid

Base Information

• Chemical Name: (2S,5S)-thiolane-2,5-dicarboxylic acid
• CAS No.: 17694-78-9
• Molecular Formula: C₆H₈O₄S
• Molecular Weight: 176.193
• DSSTox Substance ID: DTXSID501031039
• Mol file: 17694-78-9.mol

Synonyms:128945-82-4;(2S,5S)-thiolane-2,5-dicarboxylic acid;DTXSID501031039;rac-(2R,5R)-thiolane-2,5-dicarboxylic acid;EN300-1695581;2,3,4,5-Tetradeoxy-2,5-epithio-D-threo-hexaric acid;17694-78-9

Chemical Property of (2S,5S)-thiolane-2,5-dicarboxylic acid

Chemical Property:

• XLogP3: 0.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 176.01432991
• Heavy Atom Count: 11
• Complexity: 171

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1CC(SC1C(=O)O)C(=O)O
• Isomeric SMILES: C1C[C@H](S[C@@H]1C(=O)O)C(=O)O

Technology Process of (2S,5S)-thiolane-2,5-dicarboxylic acid

There total 7 articles about (2S,5S)-thiolane-2,5-dicarboxylic acid 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: 76.0%

dimethyl tetrahydrothiophene-2,5-dicarboxylate (19438-91-6,51483-80-8,111138-56-8) → (-)-tetrahydrothiophene-2,5-dicarboxylic acid (17694-78-9,17773-22-7,111138-62-6,128945-82-4)

Guidance literature:

With hydrogenchloride; at 60 - 70 ℃; for 5h;

DOI:10.1248/cpb.35.2266

Reference yield:

dimethyl 2,5-dibromohexanedioate (868-72-4,53490-47-4,124819-17-6) → (-)-tetrahydrothiophene-2,5-dicarboxylic acid (17694-78-9,17773-22-7,111138-62-6,128945-82-4)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium sulfide monohydrate / tetra-n-butylammonium bromide / benzene / 5 h / Ambient temperature

2: sodium methoxide / methanol

3: 76 percent / conc. HCl / 5 h / 60 - 70 °C

With hydrogenchloride; sodium sulfide; sodium methylate; tetrabutylammomium bromide; In methanol; benzene;

DOI:10.1248/cpb.35.2266

Reference yield:

Adipic acid dichloride (111-50-2) → (-)-tetrahydrothiophene-2,5-dicarboxylic acid (17694-78-9,17773-22-7,111138-62-6,128945-82-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 80 °C / Inert atmosphere; Acidic conditions

1.2: 80 °C / Inert atmosphere

2.1: sodiumsulfide nonahydrate / N,N-dimethyl-formamide / 4 h / -40 - 0 °C

3.1: lithium hydroxide / water; tetrahydrofuran / 2 h / 0 - 25 °C

With sodiumsulfide nonahydrate; lithium hydroxide; In tetrahydrofuran; water; N,N-dimethyl-formamide;

DOI:10.1055/s-0033-1338865

upstream raw materials:

dimethyl tetrahydrothiophene-2,5-dicarboxylate

cis-2,5-dicarbomethoxytetrahydrothiophene

dimethyl 2,5-dibromohexanedioate

(2R,5R)-Tetrahydro-thiophene-2,5-dicarboxylic acid monomethyl ester

Downstream raw materials:

di-L-menthyl tetrahydrothiophene-2,5-dicarboxylate

di-L-menthyl tetrahydrothiophene-2,5-dicarboxylate