3'-(3-(3-Azido-2,3-dideoxy-beta-D-erythro-pentofuranosyl)-3,6-dihydro-5-methyl-2,6-dioxo-1(2H)-pyrimidinyl)-3'-deoxythymidine
Basic information
- CAS
148665-49-0- Standard SMILES
Cc1cn([C@H]2C[C@H](n3c(=O)c(C)cn([C@H]4C[C@H](N=[N+]=[N-])[C@@H](CO)O4)c3=O)[C@@H](CO)O2)c(=O)[nH]c1=O- InChIKey
FOSHPJRCRHGLRP-KPRKPIBOSA-N- Molecular formula
- C20H25N7O8
- Average molar mass
- 491.5 g/mol
- Monoisotopic mass
- 491.17646078
Names & identifiers
- Preferred name
- 3'-(3-(3-Azido-2,3-dideoxy-beta-D-erythro-pentofuranosyl)-3,6-dihydro-5-methyl-2,6-dioxo-1(2H)-pyrimidinyl)-3'-deoxythymidine
- IUPAC
- 1-[(2R,4S,5S)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-3-[(2S,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]-5-methylpyrimidine-2,4-dione
- English name
- Zidovudine USP Impurity G
- Molecular formula
- C20H25N7O8
- Molecular weight
- 491.46
Names & synonyms
148665-49-0Zidovudine EP Impurity GUNII-WF6985DLTUWF6985DLTUZidovudine impurity G [USP-MC]3'-(3-(3-Azido-2,3-dideoxy-beta-D-erythro-pentofuranosyl)-3,6-dihydro-5-methyl-2,6-dioxo-1(2H)-pyrimidinyl)-3'-deoxythymidine1-[(2R,4S,5S)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-3-[(2S,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]-5-methylpyrimidine-2,4-dione3'-[3-(3-Azido-2,3-dideoxy-b-D-erythro-pentofuranosyl)-3,6-dihydro-5-methyl-2,6-dioxo-1(2H)-pyrimidinyl]-3'-deoxy-thymidineThymidine, 3'-(3-(3-azido-2,3-dideoxy-beta-D-erythro-pentofuranosyl)-3,6-dihydro-5-methyl-2,6-dioxo-1(2H)-pyrimidinyl)-3'-deoxy-3-(Thymidinyl)AZTZidovudine Impurity 141-((2S,4R,5R)-4-azido-5-(hydroxymethyl)tetrahydrofuran-2-yl)-3-((2R,3R,5S)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3-yl)-5-methylpyrimidine-2,4(1H,3H)-dione
Show more names
Zidovudine DimerZidovudine USP Impurity G
Properties
Computed structural properties
- XLogP
- -0.8
- Topological polar surface area
- 163 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 10
- Rotatable bonds
- 6
- Heavy atoms
- 35
- Formal charge
- 0
- Complexity
- 1,050
Physicochemical properties
- Melting point
- 135 °C · >135°C (dec.)
- storage temp.
- -20 °C · Amber Vial, -20°C Freezer, Under inert atmosphere
- solubility
- DMSO (Slightly), Methanol (Slightly)
- form
- Solid
- pka
- 9.638 · 9.638±0.10(predicted)
- color
- White to Off-White
- Stability
- Light Sensitive
- FDA UNII
- 6985 DLTU · WF6985DLTU
Chemistry & industry
Applications
Uses3''-[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.
Related reactions
0 records
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Compound notes
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