136846-20-3

Basic information

• Product Name: 5'-Epi-LaMivudine
• Synonyms: 5'-Epi-LaMivudine;2'-Epi-LaMivudine;(2S-trans)-4-AMino-1-[2-(hydroxyMethyl)-1,3-oxathiolan-5-yl]-2(1H)-pyriMidinone;4-AMino-1-[(2S,5S)-2-(hydroxyMethyl)-1,3-oxathiolan-5-yl]-2(1H)-pyriMidinone;trans(-)-2-HydroxyMethyl-5-(cytosin-1-yl)-1,3-oxathiolane;Lamivudine Impurity 4 (Lamivudine Diastereoisomer);Lamivudine Diastereoisomer
• CAS NO: 136846-20-3
• Molecular Formula: C₈H₁₁N₃O₃S
• Molecular Weight: 229.25624
• Product Categories: Amines;Anti-virals;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Sulfur & Selenium Compounds;Amines, Anti-virals, Heterocycles, Pharmaceuticals, Intermediates & Fine Chemicals, Sulfur & Selenium Compounds
• Mol File: 136846-20-3.mol
• Article Data: 25

Chemical Properties

• Melting Point: 172.6 °C(Solv: water (7732-18-5); methanol (67-56-1))
• Boiling Point: 475.4°Cat760mmHg
• Flash Point: 241.3°C
• Appearance: /
• Density: 1.73g/cm³
• Storage Temp.: -20°C Freezer
• Solubility: DMSO (Slightly), Water (Slightly)
• PKA: 13.83±0.10(Predicted)
• CAS DataBase Reference: 5'-Epi-LaMivudine(CAS DataBase Reference)
• NIST Chemistry Reference: 5'-Epi-LaMivudine(136846-20-3)
• EPA Substance Registry System: 5'-Epi-LaMivudine(136846-20-3)

Safety Data

• Hazardous Substances Data: 136846-20-3(Hazardous Substances Data)

Usage

Description

5'-Epi-LaMivudine, also known as 2'-Epi-LaMivudine (Lamivudine EP Impurity B), is an epimer of Lamivudine (L172500). It is a derivative of the antiviral drug Lamivudine, which is primarily used to inhibit the activity of HIV-reverse transcriptase. This modification in the molecular structure of the original drug may result in different properties and applications.

Uses

Used in Pharmaceutical Industry:
5'-Epi-LaMivudine is used as an antiviral agent for inhibiting HIV-reverse transcriptase. As an epimer of Lamivudine, it has the potential to be utilized in the development of new antiviral therapies targeting HIV and other retroviruses. Its specific role in this context is to interfere with the replication process of the virus, thereby helping to manage and treat HIV infections.
Additionally, due to its structural similarity to Lamivudine, 5'-Epi-LaMivudine may also be used in research and development for understanding the structure-activity relationship of antiviral drugs. This knowledge can be applied to design more effective and targeted treatments for various viral infections.

Upstream product

• 14631-20-0 4-N-Acetylcytosine 
• 143919-90-8 2-benzoyloxymethyl-5-acethoxy-1,3-oxathiolane 
• 18531-99-2 (S)-[1,1']-binaphthalenyl-2,2'-diol 
• 131086-21-0 (+/-)-cis-N-<2-(hydroxymethyl)-1,3-oxathiolan-5-yl>cytosine 
• 136794-49-5 (+)-(2S,5R)-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>-N₄-acetylcystosine 
• 1091585-30-6 ((2R,5S)-5-(4-acetamido-2-oxopyrimidin-1(2H)-yl)-1,3-oxathiolan-2-yl)methyl benzoate 
• 147126-73-6 (1'S,2'R,5'S)-Menthyl 5(R)-cytosin-1''-yl-1,3-oxathiolane-2(S)-carboxylate 
• 145416-33-7 (+)-(2S,5R)-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>-cystosine 
• 1346921-53-6 L-menthyl 5-cytosin-1-yl-1,3-oxathiolane-2-carboxylate 
• 358348-70-6 cis/trans-2-benzoyloxymethyl-5-(cytosin-1'-yl)-1,3-oxathiolane 
• 1091585-30-6 cis-2-benzoyloxymethyl-5-(N'4-acetylcytosin-1'-yl)-1,3-oxathiolane 
• 136831-90-8 cis-2-<<(tert-butyldiphenylsilyl)oxy>methyl>-5-(cytosin-1'-yl)-1,3-oxathiolane 
• 136846-19-0 (-)-(2S,5S)-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>-N₄-acetylcystosine 

Downstream Products

• 131086-21-0 lamivudine 
• 134678-17-4 lamivudine 
• 131086-23-2 cis-2-hydroxymethyl-5-(cytosin-1'-yl)-3-oxo-1,3-oxathiolane 
• 172912-08-2 cis-2-(tert-butyldiphenylsilyloxymethyl)-5-4-(Boc-AHPPA-1-oxo-6-aminopentyl)cytosin-1'-yl>-1,3-oxathiolane 

Relevant articles and documents

Synthesis of (±)-Emtricitabine and (±)-Lamivudine by Chlorotrimethylsilane-Sodium Iodide-Promoted Vorbrüggen Glycosylation

By simple combination of water and sodium iodide (NaI) with chlorotrimethylsilane (TMSCl), promotion of a Vorbrüggen glycosylation en route to essential HIV drugs emtricitabine (FTC) and lamivudine (3TC) is achieved. TMSCl-NaI in wet solvent (0.1 M water)

METHODS FOR THE TREATMENT OF HEPATITIS B AND HEPATITIS D VIRUS INFECTIONS

It is disclosed a method for treating hepatitis B virus infection or hepatitis B virus/hepatits delta virus co-infection, the method comprising administering to a subject in need of such treatment a first pharmaceutically acceptable agent that comprises at least one phosphorothioated nucleic acid polymer and a second pharmaceutically acceptable agent that comprises at least one nucleoside/nucleotide analog HBV polymerase inhibitor.

OPTICAL RESOLUTION OF SUBSTITUTED 1, 3-OXATHIOLANE NUCLEOSIDES

Cis(±)-4-Amino-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-2(1H)-pyrimidinone is reacted with S(+)-1,1′-binaphthyl-2,2′-diyl hydrogen phosphate in methanol to obtain diastereomeric compounds. The diastereomeric compounds are subjected to selective crystallization to obtain (2R-Cis)-4-Amino-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-2(1H)-pyrimidinone 1,1′-binaphthyl-2,2′-diyl hydrogen phosphate. (2R-Cis)-4-Amino-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-2(1H)-pyrimidinone 1,1′-binaphthyl-2,2′-diyl hydrogen phosphate is treated with hydrochloric acid in water to obtain (2R-cis)-4-Amino-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-2(1H)-pyrimidinone.