2',3'-Di-O-acetyl-5'-deoxy-5-fuluro-D-cytidine structure

3D Mol Similar

2',3'-Di-O-acetyl-5'-deoxy-5-fuluro-D-cytidine

: Iupac Name：[(2R,3R,4R,5R)-4-acetyloxy-5-(4-amino-5-fluoro-2-oxopyrimidin-1-yl)-2-methyloxolan-3-yl] acetate; CAS No.: 161599-46-8; Molecular Weight：329.28; Modify Date.: 2022-11-25 02:25; Introduction:
White to Off-White SolidChEBI: A member of the class of cytidines that is a metabolite of the drug capecitabine.
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1. Names and Identifiers

: 1.1 Name; 2',3'-Di-O-acetyl-5'-deoxy-5-fuluro-D-cytidine; 1.2 Synonyms; (2R,3R,4R,5R)-2-(4-aMino-5-fluoro-2-oxopyriMidin-1(2H)-yl)-5-Methyltetrahydrofuran-3,4-diyl diacetate [(2R,3R,4R,5R)-4-acetyloxy-5-(4-amino-5-fluoro-2-oxopyrimidin-1-yl)-2-methyloxolan-3-yl] acetate 1-(2,3-Di-O-acetyl-5-deoxy-Β-D-ribofuranosyl)-5-fluoro-4-imino-1,4-dihydro-2-pyrimidinol 2,3-diACETATE 5,DEOXY 5,FLUORO CYTIDINE 2',3'-Di-O-acetyl-5'-deoxy-5-fluorocytidine 2',3'-Di-O-acetyl-5'-deoxy-5-fluoro-D-cytidine 2',3'-di-O-acetyl-5'-deoxy-5-fulurocytidine 2,3-Di-O-Acetyl-5-Deoxy-5-Fuluro-D-Cytidine 2-Pyrimidinol, 1-(2,3-di-O-acetyl-5-deoxy-Β-D-ribofuranosyl)-5-fluoro-1,4-dihydro-4-imino- 5'-Deoxy-2',3'-di-O-acetyl-5-fluorocytidine Capecitabine Impurity C (EP ) Capecitabine Impurity M Capecitabine USP IMp.D Cytidine, 5'-deoxy-5-fluoro-, 2',3'-diacetate Cytidine,5'-deoxy-5-fluoro-, 2',3'-diacetate InterMediate of Capecitabine T6NVNJ DZ EF A- BT5OTJ COV1 DOV1 E1 &&Ribo-Β-D Form; View all

1.3 CAS No.: 161599-46-8

1.4 CID: 11809635

1.5 EINECS(EC#): 605-260-4

1.6 Molecular Formula: C13H16FN3O6 (isomer)

1.7 Inchi: InChI=1S/C13H16FN3O6/c1-5-9(22-6(2)18)10(23-7(3)19)12(21-5)17-4-8(14)11(15)16-13(17)20/h4-5,9-10,12H,1-3H3,(H2,15,16,20)/t5-,9-,10-,12-/m1/s1

1.8 InChIkey: NWJBWNIUGNXJGO-RPULLILYSA-N

1.9 Canonical Smiles: CC1C(C(C(O1)N2C=C(C(=NC2=O)N)F)OC(=O)C)OC(=O)C

1.10 Isomers Smiles: C[C@@H]1[C@H]([C@H]([C@@H](O1)N2C=C(C(=NC2=O)N)F)OC(=O)C)OC(=O)C

2. Properties

2.1 Density: 1.57

2.1 Melting point: 196-198?C

2.1 Boiling point: 427.4 oC at 760 mmHg

2.1 Refractive index: 1.609

2.1 Flash Point: 212.3 oC

2.1 Precise Quality: 329.10200

2.1 PSA: 122.74000

2.1 logP: 0.32650

2.1 Appearance: WHITE

2.2 Storage: -20°C Freezer

2.3 Chemical Properties: White to Off-White Solid

2.4 Color/Form: Powder

2.5 pKa: 2.49±0.10(Predicted)

2.6 StorageTemp: Keep in dark place,Sealed in dry,2-8°C

3. Use and Manufacturing

3.1 Definition: ChEBI: A member of the class of cytidines that is a metabolite of the drug capecitabine. 2',3'-Di-O-acetyl-5'-deoxy-5-fuluro-D-cytidineSupplier

3.2 Methods of Manufacturing: 5-Fluorocytosine (200.0 g, 1.55 mol) was suspended in 2 L of dichloromethane.1, 2, 3-Tri-O-acetyl-5-deoxyribose (403.0 g, 1.55 mol) was added at room temperature.Control temperature 10 to 20 C, Titanium tetrachloride (403.0 g, 1.55 mol) was added dropwise to a 1 L solution of dichloromethane under rapid stirring.After the completion of the dropwise addition, the reaction was continued at 10 to 20 C for 4 hours.Add sodium bicarbonate (781.0 g, 9.3 mol), Slowly add 100g of water, Stirring was continued for 3 hours after the completion of the dropping.After filtration, the filter cake was washed with dichloromethane (0.4 L×2), and the filtrate was washed once with saturated aqueous sodium hydrogencarbonate (2.0 L) and the organic phase was dried over anhydrous sodium sulfate (200 g) for 1 hour, filtered, and the filtrate was concentrated under reduced pressure to syrup.The residue was recrystallized from 2.0 L of isopropanol to afford 452 g of capecitabine intermediate as a white powder.The yield was 88.6%, the purity was 99.7%, and the maximum single impurity was 0.11%. The alpha-isomer was not detected.Figure 5 is a HPLC analysis of the capecitabine intermediate.Under nitrogen atmosphere, 1.80 kg of toluene, 125 g of compound of formula III, 2 g of ammonium sulfate and 247 g of HMDS were charged into the reaction vessel. After the addition was completed, the mixture was heated to reflux under warming and the mixture was refluxed for 3 hours. The solvent was concentrated under reduced pressure and the residue was dissolved with 1.40 Kg of CH2Cl2. 225 g of the compound of formula II was added and protected by nitrogen. The mixture was cooled to -5 C and 255 g of SnCl4 / 200 g of CH2Cl2 solution was added dropwise. Natural warming reaction to the point of disappearance of raw materials. Cool to about 5 , add 400g sodium bicarbonate, stirring, dropping 187.5g purified water, stirring at room temperature. Feed filtration, the filter cake was washed with 500g CH2Cl2 beating, drained. The filtrate was washed twice with 840 g of 5% aqueous sodium bicarbonate and once with 840 g of saturated brine and dried over anhydrous sodium sulfate. The desiccant was filtered off and the solvent was concentrated under reduced pressure to give a white solid. Add 500g of anhydrous ethanol to dissolve, filter, and dry to give a white solid (242.3g, 0.736mol, 83.6%), HPLC content of 98.39%.; View all

3.3 Usage: Capecitabine intermediate

4. Safety and Handling

4.1 Safety Statements: 24/25

4.1 Hazard Declaration: H315

4.1 Caution Statement: P201, P202, P264, P273, P280, P281, P302+P352, P305+P351+P338, P308+P313, P321, P332+P313, P337+P313, P362, P391, P405, P501

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Germ cell mutagenicity, Category 2

Carcinogenicity, Category 1B

Reproductive toxicity, Category 1B

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Danger
Hazard statement(s)	H341 Suspected of causing genetic defects H350 May cause cancer H360 May damage fertility or the unborn child
Precautionary statement(s)
Prevention	P201 Obtain special instructions before use. P202 Do not handle until all safety precautions have been read and understood. P280 Wear protective gloves/protective clothing/eye protection/face protection.
Response	P308+P313 IF exposed or concerned: Get medical advice/ attention.
Storage	P405 Store locked up.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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6. Synthesis Route

161599-46-8Total: 6 Synthesis Route

66335-38-4 154 Suppliers

161599-46-8 303 Suppliers

Literatures:
US5472949 A1, ;
Yield: null

880633-97-6

161599-46-8 303 Suppliers

Literatures:
WO2006/32921 A1, ; Page/Page column 25 ;
Yield: null

108-24-7

66335-38-4 154 Suppliers

161599-46-8 303 Suppliers

Literatures:
WO2009/42613 A1, ; Page/Page column 56 ;
Yield: null

View all

7. Precursor and Product

precursor:

2022-85-7

41108-04-7

27821-07-4

880633-97-6

37076-71-4

66335-38-4

product :

124012-42-6

154361-50-9

162204-20-8

66335-38-4

8. Other Information

8.0 Storage Conditions: 5-Fluorocytosine (200.0 g, 1.55 mol) was suspended in 2 L of dichloromethane.1, 2, 3-Tri-O-acetyl-5-deoxyribose (403.0 g, 1.55 mol) was added at room temperature.Control temperature 10 to 20 C, Titanium tetrachloride (403.0 g, 1.55 mol) was added dropwise to a 1 L solution of dichloromethane under rapid stirring.After the completion of the dropwise addition, the reaction was continued at 10 to 20 C for 4 hours.Add sodium bicarbonate (781.0 g, 9.3 mol), Slowly add 100g of water, Stirring was continued for 3 hours after the completion of the dropping.After filtration, the filter cake was washed with dichloromethane (0.4 L×2), and the filtrate was washed once with saturated aqueous sodium hydrogencarbonate (2.0 L) and the organic phase was dried over anhydrous sodium sulfate (200 g) for 1 hour, filtered, and the filtrate was concentrated under reduced pressure to syrup.The residue was recrystallized from 2.0 L of isopropanol to afford 452 g of capecitabine intermediate as a white powder.The yield was 88.6%, the purity was 99.7%, and the maximum single impurity was 0.11%. The alpha-isomer was not detected.Figure 5 is a HPLC analysis of the capecitabine intermediate.Under nitrogen atmosphere, 1.80 kg of toluene, 125 g of compound of formula III, 2 g of ammonium sulfate and 247 g of HMDS were charged into the reaction vessel. After the addition was completed, the mixture was heated to reflux under warming and the mixture was refluxed for 3 hours. The solvent was concentrated under reduced pressure and the residue was dissolved with 1.40 Kg of CH2Cl2. 225 g of the compound of formula II was added and protected by nitrogen. The mixture was cooled to -5 C and 255 g of SnCl4 / 200 g of CH2Cl2 solution was added dropwise. Natural warming reaction to the point of disappearance of raw materials. Cool to about 5 , add 400g sodium bicarbonate, stirring, dropping 187.5g purified water, stirring at room temperature. Feed filtration, the filter cake was washed with 500g CH2Cl2 beating, drained. The filtrate was washed twice with 840 g of 5% aqueous sodium bicarbonate and once with 840 g of saturated brine and dried over anhydrous sodium sulfate. The desiccant was filtered off and the solvent was concentrated under reduced pressure to give a white solid. Add 500g of anhydrous ethanol to dissolve, filter, and dry to give a white solid (242.3g, 0.736mol, 83.6%), HPLC content of 98.39%.; View all

8.1 Use Classification: Pharmaceuticals

8.2 Uses: A metabolite of Capecitabine. Capecitabine Diacetyl Amino Impurity (USP).

8.3 Chemical Properties: White to Off-White Solid

8.4 Uses: Capecitabine intermediate

8.5 Uses: A metabolite of Capecitabine.

8.6 Definition: ChEBI: A member of the class of cytidines that is a metabolite of the drug capecitabine.

9. Computational chemical data

Molecular Weight: 329.28g/mol
Molecular Formula: C₁₃H₁₆FN₃O₆
Compound Is Canonicalized: True
XLogP3-AA: -0.7
Exact Mass: 329.10231340
Monoisotopic Mass: 329.10231340
Complexity: 605
Rotatable Bond Count: 5
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 7
Topological Polar Surface Area: 121
Heavy Atom Count: 23
Defined Atom Stereocenter Count: 4
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADceBzOQAAAAAAAAAAAAAAAAAAASAAAAAgAAAAAAAAAAAAAAAAHwAQAAAACBThgAYDCANABACoAAL2fACAAAEAAAAAAAAIABCDAAIAgAAPAAAHBgISAACwAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==

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Cytidine,5'-deoxy-5-fluoro-, 2',3'-diacetate