1091585-30-6

Basic information

• Product Name: N-Acetyl O-Benzyl LaMivudine
• Synonyms: N-Acetyl O-Benzyl LaMivudine
• CAS NO: 1091585-30-6
• Molecular Formula: C17H17N3O5S
• Molecular Weight: 375.39898
• Product Categories: Anti-virals;Intermediates & Fine Chemicals;Pharmaceuticals;Sulfur & Selenium Compounds;Anti-virals, Pharmaceuticals, Intermediates & Fine Chemicals, Sulfur & Selenium Compounds
• Mol File: 1091585-30-6.mol

Chemical Properties

• Appearance: /
• Storage Temp.: -20°C Freezer
• Solubility: Methanol
• CAS DataBase Reference: N-Acetyl O-Benzyl LaMivudine(CAS DataBase Reference)
• NIST Chemistry Reference: N-Acetyl O-Benzyl LaMivudine(1091585-30-6)
• EPA Substance Registry System: N-Acetyl O-Benzyl LaMivudine(1091585-30-6)

Safety Data

• Hazardous Substances Data: 1091585-30-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
N-Acetyl O-Benzyl LaMivudine is used as an antiviral agent for the treatment of chronic hepatitis B. It functions as a nucleoside reverse transcriptase inhibitor, helping to control the replication of the hepatitis B virus and manage the disease's progression.
Used in Antiviral Applications:
N-Acetyl O-Benzyl LaMivudine is used as an antiviral agent to combat viral infections, particularly those caused by retroviruses. Its role as a reverse transcriptase inhibitor makes it effective in preventing the synthesis of viral DNA, thereby limiting the spread of the virus within the host.

Upstream product

• 143919-90-8 2-benzoyloxymethyl-5-acethoxy-1,3-oxathiolane 
• 54230-57-8 N⁴-acetyl-O-trimethylsilylcytosine 
• 143919-90-8 ((2R)-5-acetoxy-1,3-oxathiolan-2-yl)methyl benzoate 
• 14631-20-0 4-N-Acetylcytosine 
• 96472-73-0 bis-TMS-N-acetylcytosine 
• 528567-33-1 5-methoxy-2-benzoyloxymethyl[1,3]oxathiolane 
• 144897-15-4 2-benzoyloxymethyl-5-<2-methoxyethyloxy>-1,3-oxathiolane 
• 64904-47-8 2-benzoyloxyacetaldehyde 
• 108-24-7 acetic anhydride 
• 358348-70-6 cis/trans-2-benzoyloxymethyl-5-(cytosin-1'-yl)-1,3-oxathiolane 

Downstream Products

• 134678-17-4 lamivudine 
• 139757-68-9 (+)-(2R,5R)-1-<2-(hydroxymethyl)-1,3-oxathiolan-5-yl>cytosine 
• 136831-90-8 cis-2-<<(tert-butyldiphenylsilyl)oxy>methyl>-5-(cytosin-1'-yl)-1,3-oxathiolane 

Relevant articles and documents

Efficient asymmetric synthesis of lamivudine via enzymatic dynamic kinetic resolution

The anti-HIV nucleoside lamivudine was asymmetrically synthesized in only three steps via a novel surfactant-treated subtilisin Carlsberg-catalyzed dynamic kinetic resolution protocol. The enantiomer of lamivudine could also be accessed using the same protocol catalyzed by Candida antarctica lipase B.

A PROCESS FOR STEREOSELECTIVE SYNTHESIS OF LAMIVUDINE

The present invention discloses a process for stereoselective synthesis of Lamivudine comprising the following steps: (a) performing a glycosylation reaction between the compound of formula (I) and cytosine or protected cytosine, and separating the reaction product by recrystallization to obtain the intermediate of formula (II); and (b) deprotecting the intermediate of formula (II) to obtain Lamivudine.

PROCESS FOR PREPARING SUBSTITUTED 1,3-OXATHIOLANES WITH ANTIVIRAL PROPERTIES

Disclosed are processes for preparing compounds of formula (I) and pharmaceutically acceptable salts or esters thereof, wherein R2 is a purine or pyrimidine base or an analogue or derivative thereof; and Z is S, S = O or SO2. The invention also relates to

2-Substituted-4-substituted-1,3-dioxolanes and use thereof

Nucleoside analogues containing a 1,3-dioxolane structure are suitable antiviral agents, particulary for the treatment of the HIV infections in mammals, especially humans. Examples of the nucleoside analogues include: cis-2-acetoxymethyl-4-(thymin-1′-yl)-1,3,-dioxolane, cis-2-hydroxymethyl-4-(thymin-1′-yl)-1,3-dioxolane, cis-2-benzoyloxymethyl-4-(cytosin-1′-yl)-1,3-dioxolane, and cis-2-hydroxymethyl-4-(cytosin-1′-yl)-1,3-dioxolane. These compounds can be in the form of their racemates or their separate enantiomers.

Processes for preparing substituted 1,3-oxathiolanes with antiviral properties

Disclosed are processes for preparing compounds of the formula (I) and pharmaceutically acceptable salts or esters thereof: STR1 wherein R2 is a purine or pyrimidine base or an analogue or derivative thereof; and Z is S, S=O or SO2.

Enantioselective enzymatic synthesis of the anti-viral agent lamivudine (3TC)

A novel enzymatic resolution of α-acetoxysulfides has been used as the key step in the synthesis of the important antiviral nucleoside analogue lamivudine. The synthesis proceeds via a configurationally stable hemithioacetal which cyclises in situ to form the required oxathiolane nucleus, which can then be converted into the target nucleoside in 4 steps.