139757-68-9

Basic information

• Product Name: REF DUPL: trans-2-Hydroxymethyl-5-(cytosin-1-yl)-1,3-oxathiolane
• Synonyms: REF DUPL: .alpha.-L-(+)-(2R,5R)-1-[2-(Hydroxymethyl)-1,3-oxathiolan-5-yl]cytosine;REF DUPL: .alpha.-L-Oxathionyl-cytidine;REF DUPL: 2(1H)-Pyrimidinone, 4-amino-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-, (2R-trans)-;REF DUPL: Aids002618;REF DUPL: Aids-002618;REF DUPL: trans-2-Hydroxymethyl-5-(cytosin-1-yl)-1,3-oxathiolane;3’-Epi Lamivudine;(2R-trans)-4-AMino-1-[2-(hydroxyMethyl)-1,3-oxathiolan-5-yl]-2(1H)-pyriMidinone
• CAS NO: 139757-68-9
• Molecular Formula: C₈H₁₁N₃O₃S
• Molecular Weight: 229.25624
• Product Categories: Anti-virals;Intermediates & Fine Chemicals;Pharmaceuticals;Sulfur & Selenium Compounds;Anti-virals, Pharmaceuticals, Intermediates & Fine Chemicals, Sulfur & Selenium Compounds
• Mol File: 139757-68-9.mol
• Article Data: 28

Chemical Properties

• Melting Point: 168.0 °C(Solv: ethanol (64-17-5); water (7732-18-5))
• Boiling Point: 475.4°Cat760mmHg
• Flash Point: 241.3°C
• Appearance: /
• Density: 1.73g/cm³
• Vapor Pressure: 4.91E-11mmHg at 25°C
• Refractive Index: 1.754
• Storage Temp.: -20°C Freezer
• Solubility: Methanol (Slightly, Sonicated), Water (Slightly)
• PKA: 13.83±0.10(Predicted)
• CAS DataBase Reference: REF DUPL: trans-2-Hydroxymethyl-5-(cytosin-1-yl)-1,3-oxathiolane(CAS DataBase Reference)
• NIST Chemistry Reference: REF DUPL: trans-2-Hydroxymethyl-5-(cytosin-1-yl)-1,3-oxathiolane(139757-68-9)
• EPA Substance Registry System: REF DUPL: trans-2-Hydroxymethyl-5-(cytosin-1-yl)-1,3-oxathiolane(139757-68-9)

Safety Data

• Hazardous Substances Data: 139757-68-9(Hazardous Substances Data)

Usage

Chemical Properties

Pale Beige Solid

Uses

Lamivudine epimer.

InChI:InChI=1/C8H11N3O3S/c9-5-1-2-11(8(13)10-5)6-4-15-7(3-12)14-6/h1-2,6-7,12H,3-4H2,(H2,9,10,13)/t6-,7-/m1/s1

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 
• 145985-98-4 (2R,5R)-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>cytosine 
• 139757-73-6 (2R,5R)-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>-N⁴-acetylcytosine 

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

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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)

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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.