N-Acetyl O-Benzyl LaMivudine

Base Information

• Chemical Name: N-Acetyl O-Benzyl LaMivudine
• CAS No.: 1091585-30-6
• Molecular Formula: C₁₇H₁₇N₃O₅S
• Molecular Weight: 375.405
• Mol file: 1091585-30-6.mol

Synonyms:

Chemical Property of N-Acetyl O-Benzyl LaMivudine

Chemical Property:

• Storage Temp.: -20°C Freezer
• Solubility.: Methanol

Purity/Quality:

N-Acetyl O-Benzyl Lamivudine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: (N-Acetyl O-Benzyl Lamivudine) Protected Lamivudine (L172500), a potent nucleoside reverse transcriptase inhibitor, used for treatment of chronic hepatitis B. Antiviral.

Technology Process of N-Acetyl O-Benzyl LaMivudine

There total 12 articles about N-Acetyl O-Benzyl LaMivudine 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: 60.0%

bis-TMS-N-acetylcytosine (96472-73-0) + 5-methoxy-2-benzoyloxymethyl[1,3]oxathiolane (528567-33-1,139253-83-1) → ((2R,5S)-5-(4-acetamido-2-oxopyrimidin-1(2H)-yl)-1,3-oxathiolan-2-yl)methyl benzoate (1091585-30-6)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 20 ℃; for 12h;

Reference yield: 51.0%

N4-acetyl-O-trimethylsilylcytosine (54230-57-8) + ((2R)-5-acetoxy-1,3-oxathiolan-2-yl)methyl benzoate (143919-90-8,143957-14-6,146726-76-3) → ((2R,5S)-5-(4-acetamido-2-oxopyrimidin-1(2H)-yl)-1,3-oxathiolan-2-yl)methyl benzoate (1091585-30-6)

Guidance literature:

With trimethylsilyl iodide; In acetonitrile; at 0 ℃; for 1.25h; Inert atmosphere;

DOI:10.1039/c3cc45551c

Reference yield:

silylated cytosine N-acetylcytosine + 2-benzoyloxymethyl-5-acethoxy-1,3-oxathiolane (143919-90-8,143957-14-6,146726-76-3) → TRANS 2-BENZOYLOXYMETHYL-5-(N4'-ACETYL CYTOSIN-1'-YL)-1,3-OXATHIOLANE (1091585-30-6)

Guidance literature:

With trimethylsilyl iodide; In nitrosyl acetate; 1,2-dichloro-ethane;

upstream raw materials:

acetic anhydride

cis/trans-2-benzoyloxymethyl-5-(cytosin-1'-yl)-1,3-oxathiolane

2-benzoyloxyacetaldehyde

2-benzoyloxymethyl-5-<2-methoxyethyloxy>-1,3-oxathiolane

Downstream raw materials:

lamivudine

(+)-(2R,5R)-1-<2-(hydroxymethyl)-1,3-oxathiolan-5-yl>cytosine

cis-2-<<(tert-butyldiphenylsilyl)oxy>methyl>-5-(cytosin-1'-yl)-1,3-oxathiolane

Refernces

• 1、 -. "A PROCESS FOR STEREOSELECTIVE SYNTHESIS OF LAMIVUDINE". Page/Page column 12. . Retrieved 2010/04/24.
• 2、 -. "2-Substituted-4-substituted-1,3-dioxolanes and use thereof". Page column 38. . Retrieved 2010/11/29.