10212-20-1

Basic information

• Product Name: 4-Amino-1-[(2R,3R,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one
• Synonyms: 4-amino-1-[(2r,3r,4r,5r)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one;4-AMINO-1-((2R,3R,4R,5R)-3-FLUORO-4-HYDROXY-5-HYDROXYMETHYL-TETRAHYDRO-FURAN-2-YL)-1H-PYRIMIDIN-2-ONE;2'-FLUORO-D-CYTIDINE;2'-DEOXY-2'-FLUOROCYTIDINE;2'-FC;2'-FLUORO-2'-DEOXYCYTIDINE;2'-DEOXY-2'-FLUOROCYTIDINE(2'-FLUORO-2'- DEOXYCYTIDINE, 2'-FC);2'-Deoxy-2'-fluoro-D-cytidine
• CAS NO: 10212-20-1
• Molecular Formula: C₉H₁₂FN₃O₄
• Molecular Weight: 245.21
• EINECS: 1806241-263-5
• Product Categories: Biochemistry;Nucleosides and their analogs;Nucleosides, Nucleotides & Related Reagents
• Mol File: 10212-20-1.mol
• Article Data: 27

Chemical Properties

• Melting Point: 167 °C
• Boiling Point: 500.1 °C at 760 mmHg
• Flash Point: 256.2 °C
• Appearance: White to Off-white/Powder
• Density: 1.82 g/cm³
• Refractive Index: 80 ° (C=1, MeOH)
• Storage Temp.: 2-8°C
• Solubility: Soluble in DMSO, Methanol.
• PKA: 12.84±0.70(Predicted)
• CAS DataBase Reference: 4-Amino-1-[(2R,3R,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Amino-1-[(2R,3R,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one(10212-20-1)
• EPA Substance Registry System: 4-Amino-1-[(2R,3R,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one(10212-20-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• Hazardous Substances Data: 10212-20-1(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

Different sources of media describe the Uses of 10212-20-1 differently. You can refer to the following data:
1. 2'-Deoxy-2'-fluorocytidine is a potent inhibitor of the subgenomic hepatitis C virus replicon in Huh-7 cells. 2'-Deoxy-2'-fluorocytidine has been shown to inhibit Borna Disease virus replication and s pread.
2. 2'-Fluoro-2'-deoxycytidine is a potent inhibitor of the subgenomic hepatitis C virus replicon in Huh-7 cells. 2'-Fluoro-2'-deoxycytidine has been shown to inhibit Borna Disease virus replication and spread.

InChI:InChI=1/C9H12FN3O4/c10-6-7(15)4(3-14)17-8(6)13-2-1-5(11)12-9(13)16/h1-2,4,6-8,14-15H,3H2,(H2,11,12,16)/t4-,6?,7-,8-/m1/s1

Synthetic route

9-<2-deoxy-2-fluoro-3,5-di-O-(tetrahydropyran-2-yl)-β-D-ribofuranosyl>cytosine (157024-78-7) → 2'-deoxy-2'-fluorocytidine (10212-20-1)

Conditions	Yield
With ethanol; pyridinium p-toluenesulfonate for 24h; Heating;	66%

3',5'-Di-O-benzoyl-2'-desoxy-2'-fluorcytidin → 2'-deoxy-2'-fluorocytidine (10212-20-1)

Conditions	Yield
With ammonium hydroxide at 50℃;	56%

Acetic acid (2R,3R,4R,5R)-2-acetoxymethyl-5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-4-fluoro-tetrahydro-furan-3-yl ester → 2'-deoxy-2'-fluorocytidine (10212-20-1)

Conditions	Yield
With N,N-dimethyl-ethanamine In methanol at 50℃; for 24h; Yield given;

cyclocitidine (31698-14-3) → 2'-deoxy-2'-fluorocytidine (10212-20-1)

Conditions	Yield
With potassium fluoride

3’,5’-O-acetyl-2’-deoxy-2’-fluorouridine (10212-13-2) → 2'-deoxy-2'-fluorocytidine (10212-20-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: (PhO)2POCl, Et3N / acetonitrile / 1.5 h / Ambient temperature 2: 32percent aq. NH3 / dioxane / 0.33 h 3: EtNMe2 / methanol / 24 h / 50 °C View Scheme

2'-deoxy-2'-fluorouridine (56287-17-3, 69123-94-0, 784-71-4) → 2'-deoxy-2'-fluorocytidine (10212-20-1)

Conditions	Yield
Multi-step reaction with 4 steps 1: 92 percent / pyridine / 2 h / Ambient temperature 2: (PhO)2POCl, Et3N / acetonitrile / 1.5 h / Ambient temperature 3: 32percent aq. NH3 / dioxane / 0.33 h 4: EtNMe2 / methanol / 24 h / 50 °C View Scheme

Acetic acid (2R,3R,4R,5R)-2-acetoxymethyl-4-fluoro-5-[4-(3-nitro-[1,2,4]triazol-1-yl)-2-oxo-2H-pyrimidin-1-yl]-tetrahydro-furan-3-yl ester (196928-90-2) → 2'-deoxy-2'-fluorocytidine (10212-20-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 32percent aq. NH3 / dioxane / 0.33 h 2: EtNMe2 / methanol / 24 h / 50 °C View Scheme

2,2'-Anhydrouridine (3736-77-4) → 2'-deoxy-2'-fluorocytidine (10212-20-1)

Conditions

Yield

Multi-step reaction with 5 steps 1: 87 percent / p-TsOH / dimethylformamide / 2.5 h / 0 °C 2: 25.1 g / 1 N aq. NaOH / methanol / 1.5 h / Ambient temperature 3: 57 percent / diethylaminosulfur trifluoride (DAST), pyridine / CH2Cl2 / 3 h / Heating 4: 1.) 4-chlorophenyl phosphorodichloridate, 1,2,4-triazole, pyridine, 2.) conc. NH4OH / 1.) RT, 2 d, 2.) dioxane, RT, 1 d 5: 66 percent / pyridinium p-toluenesulfonate (PPTS), C2H5OH / 24 h / Heating View Scheme

3',5'-di-O-(tetrahydropyran-2-yl)-2,2'-O-cyclouridine (351523-07-4) → 2'-deoxy-2'-fluorocytidine (10212-20-1)

Conditions

Yield

Multi-step reaction with 4 steps 1: 25.1 g / 1 N aq. NaOH / methanol / 1.5 h / Ambient temperature 2: 57 percent / diethylaminosulfur trifluoride (DAST), pyridine / CH2Cl2 / 3 h / Heating 3: 1.) 4-chlorophenyl phosphorodichloridate, 1,2,4-triazole, pyridine, 2.) conc. NH4OH / 1.) RT, 2 d, 2.) dioxane, RT, 1 d 4: 66 percent / pyridinium p-toluenesulfonate (PPTS), C2H5OH / 24 h / Heating View Scheme

9-<3,5-di-O-(tetrahydropyran-2-yl)-β-D-arabinofuranosyl>uracil (157024-75-4) → 2'-deoxy-2'-fluorocytidine (10212-20-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: 57 percent / diethylaminosulfur trifluoride (DAST), pyridine / CH2Cl2 / 3 h / Heating 2: 1.) 4-chlorophenyl phosphorodichloridate, 1,2,4-triazole, pyridine, 2.) conc. NH4OH / 1.) RT, 2 d, 2.) dioxane, RT, 1 d 3: 66 percent / pyridinium p-toluenesulfonate (PPTS), C2H5OH / 24 h / Heating View Scheme

9-<2-deoxy-2-fluoro-3,5-di-O-(tetrahydropyran-2-yl)-β-D-ribofuranosyl>uracil (157024-77-6) → 2'-deoxy-2'-fluorocytidine (10212-20-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) 4-chlorophenyl phosphorodichloridate, 1,2,4-triazole, pyridine, 2.) conc. NH4OH / 1.) RT, 2 d, 2.) dioxane, RT, 1 d 2: 66 percent / pyridinium p-toluenesulfonate (PPTS), C2H5OH / 24 h / Heating View Scheme

3',5'-Di-o-benzoyl-2'-desoxy-2'-fluoruridin → 2'-deoxy-2'-fluorocytidine (10212-20-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: 73 percent / p-Cl-C6H4-OP(O)Cl2 2: 82 percent / conc. aq. NH3 / dioxane / 1 h 3: 56 percent / conc. NH3 / 50 °C View Scheme

4-Tetrazolo-3',5'-di-O-benzoyl-2'-fluor-1(2H)-pyrimidinon (128963-08-6) → 2'-deoxy-2'-fluorocytidine (10212-20-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 82 percent / conc. aq. NH3 / dioxane / 1 h 2: 56 percent / conc. NH3 / 50 °C View Scheme

benzoic acid anhydride (93-97-0) + 2'-deoxy-2'-fluorocytidine (10212-20-1) → N4-benzoyl-2-deoxy-2-fluorocytidine (146954-76-9)

Conditions	Yield
In N,N-dimethyl-formamide at 20℃;	100%
In N,N-dimethyl-formamide at 20℃;	100%
In N,N-dimethyl-formamide	92%

2'-deoxy-2'-fluorocytidine (10212-20-1) → 5-bromo-2'-deoxy-2'-fluorocytidine

Conditions	Yield
With pyridine; bromine In tetrachloromethane at 20℃; for 0.416667h;	84%

tert-butyldimethylsilyl chloride (18162-48-6) + 2'-deoxy-2'-fluorocytidine (10212-20-1) → 2'-deoxy-2'-fluoro-5'-O-TBDMS-cytidine (1246253-27-9)

Conditions	Yield
With pyridine at 20℃;	82%
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 4h; regioselective reaction;	77%
With pyridine at 20℃; for 16h; Cooling with ice;
With pyridine

2'-deoxy-2'-fluorocytidine (10212-20-1) → 5-iodo-2'-deoxy-2'-(R)-fluoro-cytidine (80791-93-1)

Conditions	Yield
With iodine; 3-chloro-benzenecarboperoxoic acid In N,N-dimethyl-formamide at 20℃; for 7h;	67%
With Iodine monochloride In methanol at 50℃; for 4h;	39%
With iodine; iodic acid; acetic acid In tetrachloromethane; water at 45℃; for 4h; Iodination;

2'-deoxy-2'-fluorocytidine (10212-20-1) → 2'-deoxy-2'-fluoro-N4-hydroxycytidine

Conditions	Yield
With hydroxylamine hydrochloride; sodium hydroxide In water at 55℃; for 16h; pH=5; Inert atmosphere;	47%
With hydroxylamine hydrochloride In water at 55℃; for 16h; pH=5; Sealed tube; Inert atmosphere;	91 mg

2'-deoxy-2'-fluorocytidine (10212-20-1) → 5-chloro-2'-deoxy-2'-fluorocytidine

Conditions	Yield
With benzoyl chloride; 3-chloro-benzenecarboperoxoic acid In N,N-dimethyl-formamide at 20℃; for 0.5h;	24%

acetyl chloride (75-36-5) + 2'-deoxy-2'-fluorocytidine (10212-20-1) → Acetic acid (2R,3R,4R,5R)-2-acetoxymethyl-5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-4-fluoro-tetrahydro-furan-3-yl ester; hydrochloride

Conditions	Yield
With hydrogenchloride at 90 - 95℃; for 0.5h;

2'-deoxy-2'-fluorocytidine (10212-20-1) + 2,6-diaminopurine (1904-98-9) → 2,6-diamino-9-(2-deoxy-2-fluoro-β-D-ribofuranosyl)-9H-purine (134444-47-6)

Conditions	Yield
With E. coli BMT-4D Substitution;

2'-deoxy-2'-fluorocytidine (10212-20-1) → N-{3-[4-Amino-1-((2R,3R,4R,5R)-3-fluoro-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2-oxo-1,2-dihydro-pyrimidin-5-yl]-prop-2-ynyl}-2,2,2-trifluoro-acetamide

Conditions	Yield
Multi-step reaction with 2 steps 1: HIO3; I2; AcOH / CCl4; H2O / 4 h / 45 °C 2: CuI; (Ph3P)4P; Et3N / dimethylformamide / 16 h View Scheme

2'-deoxy-2'-fluorocytidine (10212-20-1) → 2'-deoxy-2'-fluoroguanosine (78842-13-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: E. coli BMT-4D/1A 2: ADase View Scheme

2'-deoxy-2'-fluorocytidine (10212-20-1) → N4-benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-fluoro-2'-deoxycytidine (146954-77-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 92 percent / dimethylformamide 2: 87 percent / Et3N / pyridine View Scheme

2'-deoxy-2'-fluorocytidine (10212-20-1) → N4-benzoyl-2'-deoxy-2'-fluoro-5'-O-(4,4'-dimethoxytrityl)cytidine 3'-(β-cyanoethyl N,N-diisopropylphosphoramidite) (161442-19-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: 92 percent / dimethylformamide 2: 87 percent / Et3N / pyridine 3: 90 percent / (i-Pr)2EtN / CH2Cl2 View Scheme

2'-deoxy-2'-fluorocytidine (10212-20-1) → 3',5'-di-O-acetyl-2'-deoxy-2'-fluoro-5-iodocytosine hydrochloride (83966-99-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) HCl / 0.5 h / 90 - 95 °C 2: I2, HIO3, AcOH / H2O; CCl4 / 24 h / 50 - 55 °C View Scheme

2'-deoxy-2'-fluorocytidine (10212-20-1) → N4-benzoyl-2-deoxy-2-fluorocytidine (146954-76-9)

2'-deoxy-2'-fluorocytidine (10212-20-1) + tert-butylchlorodiphenylsilane (58479-61-1) → C25H30FN3O4Si

Conditions	Yield
With dmap; triethylamine In N,N-dimethyl-formamide at 0 - 50℃; for 12h;

Upstream product

• 128963-08-6 4-Tetrazolo-3',5'-di-O-benzoyl-2'-fluor-1(2H)-pyrimidinon 
• 56287-17-3 2'-deoxy-2'-fluorouridine 
• 10212-13-2 3’,5’-O-acetyl-2’-deoxy-2’-fluorouridine 
• 31698-14-3 cyclocitidine 
• 157024-78-7 9-<2-deoxy-2-fluoro-3,5-di-O-(tetrahydropyran-2-yl)-β-D-ribofuranosyl>cytosine 
• 157024-77-6 9-<2-deoxy-2-fluoro-3,5-di-O-(tetrahydropyran-2-yl)-β-D-ribofuranosyl>uracil 
• 196928-90-2 Acetic acid (2R,3R,4R,5R)-2-acetoxymethyl-4-fluoro-5-[4-(3-nitro-[1,2,4]triazol-1-yl)-2-oxo-2H-pyrimidin-1-yl]-tetrahydro-furan-3-yl ester 
• 3736-77-4 2,2'-Anhydrouridine 
• 157024-75-4 9-<3,5-di-O-(tetrahydropyran-2-yl)-β-D-arabinofuranosyl>uracil 
• 351523-07-4 3',5'-di-O-(tetrahydropyran-2-yl)-2,2'-O-cyclouridine 

Downstream Products

• 146954-76-9 N4-benzoyl-2-deoxy-2-fluorocytidine 
• 134444-47-6 2,6-diamino-9-(2-deoxy-2-fluoro-β-D-ribofuranosyl)-9H-purine 
• 1048374-12-4 (2R,3R,4R,5R)-5-(4-benzamido-2-oxopyrimidin-1(2H)-yl)-4-fluoro-2-(hydroxymethyl)tetrahydrofuran-3-yl benzoate 
• 1048374-14-6 C₂₆H₂₅FN₃O₈P 
• 1246253-29-1 3'-O-N₄-bis(4-methoxytrityl)-2'-deoxy-2'-fluorocytidine 
• 1246253-30-4 3'-O-N₄-bis(4-methoxytrityl)-5'-C,5'-O-didehydro-2'-deoxy-2'-fluorocytidine 
• 1445379-41-8 C₅₀H₄₆FN₃O₇ 
• 1445381-83-8 C₃₇H₄₄FN₅O₆Si 
• 1445392-14-2 C₅₈H₆₂FN₅O₈Si 
• 1246253-28-0 3'-O-N₄-bis(4-methoxytrityl)-5'-O-(t-butyldimethylsilyl)-2'-deoxy-2'-fluorocytidine 
• 182495-82-5 O₅'-dimethoxytrityl-N₄-benzoyl-5-methyl-2'-deoxy-2'-(R)-fluorocytidine 

Relevant articles and documents

Synthesis and hypnotic and anti-human immunodeficiency virus-1 activities of N3-substituted 2'-deoxy-2'-fluorouridines

Reaction of 9-[3,5-di-O-(tetrahydropyran-2-yl)-β-D- arabinofuranosyl]uracil (2) with diethylaminosulfur trifluoride in the presence of pyridine afforded 2'-deoxy-2'-flouroriboside 3a, from which 2'- deoxy-2'-fluorocytidine (14b) has been synthesized in good yield. Compound 3a was deprotected and subsequently treated with various benzyl halides or 2- chloro-4-fluoroacetophenone to give corresponding N3-substituted 2'-deoxy- 2'-fluorouridines 5a-c and 6. Compounds 5a-c, as well as 6, showed weak hypnotic activity in mice. Compound 4b showed moderate antiviral activity against human immunodeficiency virus-1 but 3b, 5a-c, and 6 were virtually inactive.

Synthesis and in vitro anti-HCV activity of β-D- and L-2′-deoxy-2′-fluororibonucleosides

Based on the discovery of β-D-2′-deoxy-2′-fluorocytidine as a potent anti-hepatitis C virus (HCV) agent, a series of β-D- and L-2′-deoxy-2′-fluororibonucleosides with modifications at 5 and/or 4 positions were synthesized and evaluated for their in vitro activity against HCV and bovine viral diarrhea virus (BVDV). The introduction of the 2′-fluoro group was achieved by either fluorination of 2,2′-anhydronucleosides with hydrogen fluoride-pyridine or potassium fluoride, or a fluorination of arabinonucleosides with DAST. Among the 27 analogues synthesized, only the 5-fluoro compounds, namely β-D-2′- deoxy-2′,5-difluorocytidine (5), had anti-HCV activity in the subgenomic HCV replicon cell line, and inhibitory activity against ribosomal RNA. As β-D-N4-hydroxycytidine (NHC) had previously shown potent anti-HCV activity, the two functionalities of the N4-hydroxyl and the 2′-fluoro were combined into one molecule, yielding β-D-2′- deoxy-2′-fluoro-N4-hydroxycytidine (12). However, this nucleoside showed neither anti-HCV activity nor toxicity. All the L-forms of the analogues were devoid of anti-HCV activity. None of the compounds showed anti-BVDV activity, suggesting that the BVDV system cannot reliably predict anti-HCV activity in vitro. Copyright Taylor & Francis, Inc.

Modulation of CEACAM1 expression

Compounds, compositions and methods are provided for modulating the expression of CEACAM1. The compositions comprise oligonucleotides, targeted to nucleic acid encoding CEACAM1. Methods of using these compounds for modulation of CEACAM1 expression and for diagnosis and treatment of disease associated with expression of CEACAM1 are provided.