158798-73-3

Basic information

• Product Name: Capecitabine
• Synonyms: N(4)-Pentyloxycarbonyl-5'-deoxy-5-fluorocytidine;Pentyl N-[1-[(2R,3R,4R,5R)-3,4-dihydroxy-5-methyl-oxolan-2-yl]-5-fluoro-2-oxo-pyrimidin-4-yl]carbamate;Capiibine;Carbamic acid, (1-(5-deoxy-beta-D-ribofuranosyl)-5-fluoro-1,2-dihydro-2-oxo-4-pyrimidinyl)-, pentyl ester;Caxeta;Hsdb 7656;pentyl N-[1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-methyloxolan-2-yl]-5-fluoro-2-oxopyrimidin-4-yl]carbamate
• CAS NO: 158798-73-3
• Molecular Formula: C15H22FN3O6
• Molecular Weight: 359.35
• Mol File: 158798-73-3.mol
• Article Data: 32

Chemical Properties

• Boiling Point: 437.874°C at 760 mmHg
• Flash Point: 218.619°C
• Appearance: /
• Density: 1.49 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.7
• CAS DataBase Reference: Capecitabine(CAS DataBase Reference)
• NIST Chemistry Reference: Capecitabine(158798-73-3)
• EPA Substance Registry System: Capecitabine(158798-73-3)

Safety Data

• Hazardous Substances Data: 158798-73-3(Hazardous Substances Data)

Usage

Originator

Xeloda,Hoffmann - La Roche Inc.,USA

Therapeutic Function

Antitumor

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

Upstream product

• 61248-15-5 1,2,3,5-tetra-O-acetyl-α-D-xylofuranose 
• 532-20-7 α-D-xylofuranose 
• 638-41-5 pentyl chloroformate 
• 4137-56-8 ((3aR,4R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl 4-methylbenzenesulfonate 
• 4099-85-8 methyl 2,3-O-isopropylidene-D-ribofuranoside 
• 532-20-7 D-Ribose 
• 78341-97-6 1-O-methyl-2,3-O-isopropylidene-5-deoxy-D-ribofuranose 
• 50600-40-3 (3aS,4S,6aR)-4-(iodomethyl)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole 
• 37076-71-4 5-deoxy-1,2,3-tri-O-acetyl-D-ribofuranose 
• 41864-22-6 1,1'-Carbonyl-di-(1,2,4-triazole) 
• 2022-85-7 Flucytosine 
• 71-41-0 pentan-1-ol 
• 27821-07-4 1,2,3-tri-O-acetyl-5-deoxy-β-D-ribofuranose 
• 50610-99-6 1-O-methyl-2,3-O-isopropylidene-5-O-(methanesulfonyl)-β-D-ribofuranoside 

Downstream Products

• 66335-38-4 5'-deoxy-5-fluorocytidine 

Relevant articles and documents

Preparation of capecitabine intermediate

The invention belongs to the field of medicine synthesis, and provides a preparation method of capecitabine intermediate, in particular to a compound of the formula I II in the presence of a ketone solvent and an organic base.

Cytidine derivative and method for preparing capecitabine medicines through derivative

The invention discloses a 5-deoxy-D-ribofuranose 1-[2-(1-styyl) benzoate] derivative as shown in a general formula (I) and a preparation method of the derivative, and a method for preparing a N4-deoxycarbonyl cytidine derivative and antitumor medicines namely capecitabine by using the general formula (I) as a raw material, wherein the structure of the general formula (I) is as shown in the description. The 5-deoxy-D-ribofuranose 1-[2-(1-styyl) benzoate] derivative as the raw material of a reaction is used as a glycosyl donor and can be activated under the condition of Lewis acid trimethylsilyl trifluoromethanesulfonate and N-lodosuccinimide in catalysis quantity, so that Lewis acid in traditional use equivalent or excessive quantity is avoided, and a reaction system is mild, free from occurrence of other side reactions and efficient.

A capecitabine synthetic method

The invention belongs to the technical field of medicine preparation and relates to a synthetic method of capecitabine. The method comprises the following steps: 1) condensation reaction: reacting 2', 3'-bi-O-acetyl-5'-deoxy-5-fluoro-cytidine with halo n-amyl formate in the presence of an acid applying agent and a dimethylamino-pyridine catalyst to prepare N-pentyloxy carbonyl-2' 3'-bi-O-actyl-5'-deoxy-5-fluoro-cytidine; and 2) hydrolysis reaction: carrying out hydrolysis reaction on N-pentyloxy carbonyl-2' 3'-bi-O-actyl-5'-deoxy-5-fluoro-cytidine in the presence of an inorganic base to prepare the final product capecitabine. Compared with the prior art, the method provided by the invention has the advantages that by taking the inorganic base as the acid applying agent, use of a lot of organic bases is avoided and therefore the yield is improved, the production cost lowered, the environmental pollution is reduced, the physical health of the worker is ensured, and industrial production is facilitated.