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pd_meltingpoint:110-121 °C
Appearance:Colourless solid
Purity:99%
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An antiproliferative 5-fluorouracil releasing compound
pentyl chloroformate
(2R,3R,4R,5R)-2-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-5-methyl-tetrahydrofuran-3,4-diyl diacetate
capecitabine
| Conditions | Yield |
|---|---|
|
With
sodium hydroxide;
In
water; acetone;
at 30 ℃;
for 5h;
Green chemistry;
|
82% |
|
pentyl chloroformate; (2R,3R,4R,5R)-2-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-5-methyl-tetrahydrofuran-3,4-diyl diacetate;
With
pyridine;
In
dichloromethane;
at 0 ℃;
for 1h;
With
sodium hydroxide;
In
ethanol; water;
at -5 - 0 ℃;
for 0.233333h;
|
80.2% |
|
Multi-step reaction with 2 steps
1: dichloromethane
2: sodium hydroxide / methanol
With
sodium hydroxide;
In
methanol; dichloromethane;
|
|
|
Multi-step reaction with 2 steps
1: pyridine / dichloromethane / 1 h / 0 °C
2: sodium methylate / methanol / 1 h / 20 °C
With
pyridine; sodium methylate;
In
methanol; dichloromethane;
|
|
|
Multi-step reaction with 2 steps
1: potassium phosphate / isopropyl alcohol; dichloromethane / 4 h / 0 - 25 °C / Inert atmosphere
2: sodium hydroxide / methanol; water / 1 h / -10 - 5 °C / Autoclave
With
potassium phosphate; sodium hydroxide;
In
methanol; dichloromethane; water; isopropyl alcohol;
|
2'3'-O-isopropylidene-5'-deoxy-5-fluoro-N4-(pentyloxycarbonyl)cytidine
capecitabine
| Conditions | Yield |
|---|---|
|
With
trifluoroacetic acid;
In
methanol; dichloromethane; water;
at 10 - 20 ℃;
for 3h;
Solvent;
|
89.4% |
The CAS number of Capecitabine is 154361-50-9.
More information of Capecitabine 154361-50-9 are:
|
CAS Number |
154361-50-9 |
|
Density |
1.49 g/cm3 |
|
Melting Point |
110-121 °C |
|
Boiling Point |
437.874oC at 760 mmHg |
|
Flash Point |
218.619oC |
|
Vapor Pressure |
0mmHg at 25°C |
|
Refractive Index |
1.7 |
|
HS CODE |
29349990 |
|
PSA |
122.91000 |
|
LogP |
0.83320 |
|
Pka |
5.41±0.40(Predicted) |
Synonyms for Capecitabine 154361-50-9:Xeloda (TN);Cytidine,5'-deoxy-5-fluoro-N-[(pentyloxy)- carbonyl]-;Pentyl [1-(3,4-dihydroxy-5-methyl-oxolan-2-yl)-5-fluoro-2-oxo-pyrimidin-4-yl]aminoformate；Capecitabine;pentyl (1-((2R,3R,4S,5R)-3,4-dihydroxy-5-methyltetrahydrofuran-2-yl)-5-fluoro-2-oxo-1,2-dihydropyrimidin-4-yl)carbamate;
The chemical formula of Capecitabine is C15H22FN3O6 which containing 15 Carbon atoms,22 Hydrogen atoms,1 Fluorine atoms,3 Nitrogen atoms and 6 Oxygen atoms,and the molecular weight of Capecitabine is 359.355.
Capecitabine is a new oral fluoropyrimidine carbamate for patients with advanced neoplastic disease, approved as Xeloda for the treatment of refractory metastatic breast cancer after failure on Paclitaxel and an anthracycline-based chemotherapy regimen ; it is a prodrug of doxifluridine (5-fluorouracil ; 5-FU) activated by a cascade of 3 enzymes concentrated in human liver and cancer tissue, resulting in the selective release of 5-FU at the tumor site and offering a prolonged tumour exposure to 5-FU. Oral Capecitabine passes intact through the intestinal mucosa, is converted first by carboxylesterase to 5'-deoxy-5- fluorocytidine in the liver, then by cytidine deaminase to 5'-deoxy-5-fluorouridine in the liver and tumour tissues and finally by thymidine phosphorylase to 5-FU in tumors. Therefore, Xeloda is much safer and more effective than 5-FU (for example, in the HCT116 human colon cancer and the MX-1 breast cancer xenograft .models).
InChI:InChI=1/C9H12FN3O4/c1-3-5(14)6(15)8(17-3)13-2-4(10)7(11)12-9(13)16/h2-3,5-6,8,14-15H,1H3,(H2,11,12,16)/t3-,5-,6-,8-/m1/s1
Relevant articles related to Capecitabine:
|
Article |
Source |
|
Continuous-Flow Sequential Schotten-Baumann Carbamoylation and Acetate Hydrolysis in the Synthesis of Capecitabine |
Miranda, Leandro S. De M.,De Souza, Rodrigo O. M. A.,Lea?, Raquel A. C.,Carneiro, Paula F.,Pedraza, Sergio F.,De Carvalho, Otavio V.,De Souza, Stefania P.,Neves, Rebeca V. , p. 2516 - 2520 (2019) |
|
Cytidine derivative and method for preparing capecitabine medicines through derivative |
- Paragraph 0065-0069, (2020/05/14) |
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