cis-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-1,3-oxathiolane-2-carboxylic acid

Base Information

• Chemical Name: cis-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-1,3-oxathiolane-2-carboxylic acid
• CAS No.: 173602-25-0
• Molecular Formula: C16H18N6O8S2
• Molecular Weight: 243.24
• UNII: SGC57V0D26
• Mol file: 173602-25-0.mol

Synonyms:Lamivudine Acid;173829-09-9;173602-25-0;Lamivudine impurity A RS;rac Lamivudine Acid;cis-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-1,3-oxathiolane-2-carboxylic acid;SGC57V0D26;(2R,5S)-5-(4-amino-2-oxopyrimidin-1-yl)-1,3-oxathiolane-2-carboxylic acid;(+/-)-5-(4-Amino-2-oxopyrimidin-1(2H)-yl)-1,3-oxathiolane-2-carboxylic acid;(2R,5S)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-1,3-oxathiolane-2-carboxylic acid;(2RS,5SR)-5-(4-Amino-2-oxopyrimidin-1(2H)-yl)-1,3-oxathiolane-2-carboxylic acid;1,3-Oxathiolane-2-carboxylic acid, 5-(4-amino-2-oxo-1(2H)-pyrimidinyl)-, cis-;5-(4-Amino-2-oxopyrimidin-1(2H)-yl)-1,3-oxathiolane-2-carboxylic acid, cis-;Lamivudine-carboxylic acid;UNII-SGC57V0D26;Lamivudine impurity A [USP];SCHEMBL1335033;Lamivudine impurity A RS [USP];Lamivudine specified impurity A [EP];AKOS040752399;LAMIVUDINE IMPURITY A [EP IMPURITY];LAMIVUDINE IMPURITY A [USP IMPURITY];J-010945;Q27289192

Chemical Property of cis-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-1,3-oxathiolane-2-carboxylic acid

Chemical Property:

• Boiling Point: 546.6±60.0 °C(Predicted)
• PKA: 1.94±0.40(Predicted)
• PSA: 267.46000
• Density: 1.87±0.1 g/cm3(Predicted)
• LogP: -0.31880
• XLogP3: -1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 243.03137695
• Heavy Atom Count: 16
• Complexity: 395

Purity/Quality:

97% ^*data from raw suppliers

rac-Lamivudine acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(OC(S1)C(=O)O)N2C=CC(=NC2=O)N
• Isomeric SMILES: C1[C@H](O[C@H](S1)C(=O)O)N2C=CC(=NC2=O)N
• Uses: An impurity of the anti-viral Lamivudine (L172500).

Technology Process of cis-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-1,3-oxathiolane-2-carboxylic acid

There total 2 articles about cis-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-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: 14.0%

lamivudine (134678-17-4) → (2R,5S)-5-(cytosin-1-yl)-1,3-oxathiolane-2R-carboxylic acid (173602-25-0) + Lamivudine sulfoxide (131086-23-2)

Guidance literature:

With dipotassium peroxodisulfate; ruthenium(III) chloride trihydrate; potassium hydroxide; In water; at 25 ℃; for 8h;

DOI:10.2174/1570180811666140401184856

Reference yield:

L-menthyl 5-cytosin-1-yl-1,3-oxathiolane-2-carboxylate (1346921-53-6,147126-73-6,147126-74-7,147126-80-5) → 5-(4-amino-2-oxopyrimidine-1(2H)-yl)-1,3-oxathiolane-2-carboxylic acid (173602-25-0)

Guidance literature:

L-menthyl 5-cytosin-1-yl-1,3-oxathiolane-2-carboxylate; With potassium hydroxide; In methanol; for 4h;

With acetic acid; In water; pH=4;

DOI:10.1007/s10870-010-9866-8

upstream raw materials:

L-menthyl 5-cytosin-1-yl-1,3-oxathiolane-2-carboxylate

lamivudine