5-epi Emtricitabine

CAS: 145986-26-1

Ref. TR-E524980

Product Information

• Name: 5-epi Emtricitabine
• Synonyms: 2(1H)-Pyrimidinone, 4-amino-5-fluoro-1-[(2R,5R)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-, 2(1H)-Pyrimidinone, 4-amino-5-fluoro-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-, (2R-trans)- (9CI), 1,3-Oxathiolane, 2(1H)-pyrimidinone deriv., 4-Amino-5-fluoro-1-[(2R,5R)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-2(1H)-pyrimidinone, a-L-FTC, (2'R,5'R)-Emtricitabine

Description

Applications 5-epi Emtricitabine is an epimer of Emtricitabine (E525000), a nucleoside reverse transcriptase inhibitor approved for treatment of human immunodeficiency virus (HIV) 1, and also has antagonistic activity against the hepatitis B virus. 5-epi Emtricitabine is also used as a reagent for the synthesis of β-L-(2R,5S)- and α-L-(2R,5R)-1,3-oxathiolane-pyrimidine and -purine nucleosides as potential HIV agents.
References Jeong, L., et al.: J. Med. Chem., 36, 181 (1993); Lim, S. et al.: Arch. Intern. Med., 166, 49 (2006); Smith, K., et al.: AIDS, 23, 1547 (2009)

• Brand: TRC

Chemical properties

• Molecular weight: 247.25
• Formula: C₈H₁₀FN₃O₃S
• Color/Form: Neat
• InChI: InChI=1S/C8H10FN3O3S/c9-4-1-12(8(14)11-7(4)10)5-3-16-6(2-13)15-5/h1,5-6,13H,2-3H2,(H2,10,11,14)/t5-,6-/m1/s1
• InChI key: InChIKey=XQSPYNMVSIKCOC-PHDIDXHHSA-N
• SMILES: Nc1nc(=O)n([C@H]2CS[C@H](CO)O2)cc1F