5-hydroxy-1,3-oxathiolane-2-carboxylic Acid

Base Information

• Chemical Name: 5-hydroxy-1,3-oxathiolane-2-carboxylic Acid
• CAS No.: 147027-04-1
• Molecular Formula: C₄H₆O₄S
• Molecular Weight: 150.155
• European Community (EC) Number: 411-660-8,630-839-3
• DSSTox Substance ID: DTXSID30396721
• Mol file: 147027-04-1.mol

Synonyms:672952-08-8;5-hydroxy-1,3-oxathiolane-2-carboxylic Acid;1,3-Oxathiolane-2-carboxylicacid, 5-hydroxy-;1,3-OXATHIOLANE-2-CARBOXYLICACID,5-HYDROXY-;1,3-Oxathiolane-2-carboxylic acid, 5-hydroxy-, trans-;147027-04-1;Oprea1_485161;SCHEMBL8317054;DTXSID30396721;MFCD01871573;AKOS005096393;FT-0695441;1,3-Oxathiolane-2-carboxylic acid,5-hydroxy-;6P-110

Chemical Property of 5-hydroxy-1,3-oxathiolane-2-carboxylic Acid

Chemical Property:

• Boiling Point: 434.9±45.0 °C(Predicted)
• PKA: 2.13±0.40(Predicted)
• PSA: 92.06000
• Density: 1.697±0.06 g/cm3(Predicted)
• LogP: -0.52110
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 149.99867984
• Heavy Atom Count: 9
• Complexity: 126

Purity/Quality:

99.9% ^*data from raw suppliers

rac-trans-5-Hydroxy-1,3-oxathiolane-2-carboxylic Acid ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 22-38-41-43
• Safety Statements: 22-24-26-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(OC(S1)C(=O)O)O
• Uses: 5-Hydroxy-1,3-oxathiolane-2-carboxylic Acid is used in the synthesis of potent antiviral agent (-)-2’-Deoxy-3’-thiacytidine and its enantiomer.

Technology Process of 5-hydroxy-1,3-oxathiolane-2-carboxylic Acid

There total 3 articles about 5-hydroxy-1,3-oxathiolane-2-carboxylic 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: 70.0%

1,4-dithiane-2,5-diol (40018-26-6) + Glyoxilic acid (298-12-4) → trans-5-Hydroxy-1,3-oxathiolane-2-carboxylic acid (147027-04-1,672952-08-8)

Guidance literature:

In various solvent(s); Heating;

DOI:10.1016/j.tetlet.2005.10.002

Reference yield:

1,4-dithiane-2,5-diol (40018-26-6) + Glyoxilic acid (298-12-4) → 5-hydroxy-1,3-oxathiolane-2-carboxylic acid (147027-04-1,672952-08-8)

Guidance literature:

In tert-butyl methyl ether; cyclohexane; at 80 ℃; for 16h; Dean-Stark;

Reference yield:

glyoxalic acid monohydrate (6000-59-5,1152495-30-1) → trans-5-hydroxyoxathiolane-2-carboxylic acid (147027-04-1,672952-08-8)

Guidance literature:

In tert-butyl methyl ether; cyclohexane; water;

upstream raw materials:

1,4-dithiane-2,5-diol

Glyoxilic acid

glyoxalic acid monohydrate

Downstream raw materials:

TRANS-5-ACETOXY-1,3-OXATHIOLANE-2-CARBOXYLIC-ACID