3'-[3-(3-Azido-2,3-dideoxy-β-D-erythro-pentofuranosyl)-3,6-dihydro-5-methyl-2,6-dioxo-1(2H)-pyrimidinyl]-3'-deoxy-thymidine

CAS: 148665-49-0

Ref. TR-A825005

Product Information

• Name: 3'-[3-(3-Azido-2,3-dideoxy-β-D-erythro-pentofuranosyl)-3,6-dihydro-5-methyl-2,6-dioxo-1(2H)-pyrimidinyl]-3'-deoxy-thymidine
• Synonyms: Thymidine, 3'-[3-(3-azido-2,3-dideoxy-ß-D-erythro-pentofuranosyl)-3,6-dihydro-5-methyl-2,6-dioxo-1(2H)-pyrimidinyl]-3'-deoxy-, 3'-[3-(3-Azido-2,3-dideoxy-ß-D-erythro-pentofuranosyl)-3,6-dihydro-5-methyl-2,6-dioxo-1(2H)-pyrimidinyl]-3'-deoxythymidine, Zidovudine Imp. G (EP), 1-[(2R,4S,5S)-4-azido-5-(hydroxymethyl)tetrahydrofuran-2-yl]-3-[(2S,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3-yl]-5-methylpyrimidine-2,4(1H,3H)-dione

Description

Impurity Zidovudine USP Related Compound G
Stability Light Sensitive
Applications 3'-[3-(3-Azido-2,3-dideoxy-β-D-erythro-pentofuranosyl)-3,6-dihydro-5-methyl-2,6-dioxo-1(2H)-pyrimidinyl]-3'-deoxy-thymidine (Zidovudine USP Related Compound G) is used in the biological studies and in the preparation of N-3-substituted thymidine nucleosides as virucides as it has anti-HIV activity.
References Adams, D.R., et al.: J. Med. Chem., 40, 1550 (1997), Mainardes, R., et al.: J. Pharm. Sci., 98, 257 (2009),

• Brand: TRC

Chemical properties

• Molecular weight: 491.45
• Formula: C₂₀H₂₅N₇O₈
• Color/Form: Neat
• InChI: InChI=1S/C20H25N7O8/c1-9-5-25(19(32)22-17(9)30)16-4-12(14(8-29)35-16)27-18(31)10(2)6-26(20(27)33)15-3-11(23-24-21)13(7-28)34-15/h5-6,11-16,28-29H,3-4,7-8H2,1-2H3,(H,22,30,32)/t11-,12-,13+,14+,15+,16+/m0/s1
• SMILES: Cc1cn([C@H]2CC(n3c(=O)c(C)cn([C@H]4CC(N=[N+]=[N-])[C@H](CO)O4)c3=O)[C@H](CO)O2)c(=O)[nH]c1=O