134680-32-3

Basic information

• Product Name: ent-LaMivudine
• Synonyms: (2S-cis)-4-AMino-1-[2-(hydroxyMethyl)-1,3-oxathiolan-5-yl]-2(1H)-pyriMidinone;2',3'-Dideoxy-3'-thiacytidine;4-AMino-1-[(2S,5R)-2-(hydroxyMethyl)-1,3-oxathiolan-5-yl]-2(1H)-pyriMidinone;cis(+)-2-HydroxyMethyl-5-(cytosin-1-yl)-1,3-oxathiolane;NSC 620753;4-amino-1-((2S,5R)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl)pyrimidin-2(1H)-one;ent-LaMivudine;Lamivudine EP Impurity D
• CAS NO: 134680-32-3
• Molecular Formula: C₈H₁₁N₃O₃S
• Molecular Weight: 229.25624
• Product Categories: Pharmaceuticals;Sulfur & Selenium Compounds;Amines, Anti-virals, Heterocycles, Pharmaceuticals, Intermediates & Fine Chemicals, Sulfur & Selenium Compounds;Amines;Anti-virals;Heterocycles;Intermediates & Fine Chemicals
• Mol File: 134680-32-3.mol
• Article Data: 25

Chemical Properties

• Melting Point: 171.4 °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.: Hygroscopic, Refrigerator, Under Inert Atmosphere
• Solubility: DMSO (Slightly), Methanol (Slightly), Water (Slightly)
• PKA: 13.83±0.10(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: ent-LaMivudine(CAS DataBase Reference)
• NIST Chemistry Reference: ent-LaMivudine(134680-32-3)
• EPA Substance Registry System: ent-LaMivudine(134680-32-3)

Safety Data

• Hazardous Substances Data: 134680-32-3(Hazardous Substances Data)

Usage

Description

ent-LaMivudine, also known as Lamivudine EP Impurity D, is an enantiomer of Lamivudine (L172500). It is a compound with antiviral properties that specifically target and inhibit the activity of HIV-reverse transcriptase, a crucial enzyme in the replication process of the human immunodeficiency virus (HIV).

Uses

Used in Pharmaceutical Industry:
ent-LaMivudine is used as an antiviral agent for the treatment of HIV infection. It functions by inhibiting the HIV-reverse transcriptase enzyme, which is essential for the virus's replication process. By blocking this enzyme, ent-LaMivudine helps to prevent the spread of the virus within the body and slows down the progression of the disease.
Additionally, ent-LaMivudine may be used in research and development for the study of its antiviral properties and potential applications in the treatment of other viral infections. Its role as an enantiomer of Lamivudine also makes it a valuable compound for understanding the differences in biological activity and pharmacokinetics between enantiomers, which can be crucial in drug design and development.

Upstream product

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

Downstream Products

• 136831-90-8 cis-2-<<(tert-butyldiphenylsilyl)oxy>methyl>-5-(cytosin-1'-yl)-1,3-oxathiolane 
• 134678-17-4 lamivudine 

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.