78341-97-6

Basic information

• Product Name: Methyl-5-deoxy-2,3-O-isopropylidene-D-ribofuranoside
• Synonyms: METHYL-5-DEOXY-2,3-O-ISOPROPYLIDENE-D-RIBOFURANOSIDE;thyl-5-deoxy-2,3-O-isopropylidene-D-ribofuranoside
• CAS NO: 78341-97-6
• Molecular Formula: C₉H₁₆O₄
• Molecular Weight: 188.22
• Mol File: 78341-97-6.mol

Chemical Properties

• Boiling Point: 73-75 °C(Press: 12 Torr)
• Appearance: /
• Density: 1.11±0.1 g/cm3(Predicted)
• CAS DataBase Reference: Methyl-5-deoxy-2,3-O-isopropylidene-D-ribofuranoside(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl-5-deoxy-2,3-O-isopropylidene-D-ribofuranoside(78341-97-6)
• EPA Substance Registry System: Methyl-5-deoxy-2,3-O-isopropylidene-D-ribofuranoside(78341-97-6)

Safety Data

• Hazardous Substances Data: 78341-97-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Methyl-5-deoxy-2,3-O-isopropylidene-D-ribofuranoside is used as a key intermediate in the synthesis of Capecitabine (C175650) and its related compounds. Capecitabine is an orally administered anticancer drug that is converted into 5-fluorouracil (5-FU) in the body, which inhibits DNA synthesis and has been used to treat various types of cancer, including colorectal, breast, and ovarian cancers.
In the synthesis process, Methyl-5-deoxy-2,3-O-isopropylidene-D-ribofuranoside plays a crucial role in the formation of the final drug product, contributing to the development of new and effective cancer treatments. Its unique structure allows for specific chemical reactions that are essential for the production of Capecitabine and its analogs, making it a valuable component in the pharmaceutical industry.

Upstream product

• 52305-57-4 (3aS,4S,6aR)-4-(chloromethyl)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole 
• 4137-56-8 ((3aR,4R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl 4-methylbenzenesulfonate 
• 532-20-7 D-Ribose 
• 4099-85-8 methyl 2,3-O-isopropylidene-D-ribofuranoside 
• 50600-40-3 (3aS,4S,6aR)-4-(iodomethyl)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole 
• 78341-96-5 (3aS,4S,6aR)-4-(bromomethyl)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole 

Downstream Products

• 279673-09-5 (2R,3R,4S,5R)-5-methyltetrahydrofuran-2,3,4-triol 
• 1236199-88-4 C₁₇H₂₅FN₄O₈ 
• 27821-07-4 1,2,3-tri-O-acetyl-5-deoxy-β-D-ribofuranose 
• 154361-50-9 capecitabine 
• 162204-20-8 N¹-(2',3'-di-O-acetyl-5'-deoxy-β-D-ribofuranosyl)-5-fluoro-N⁴-(pentyloxycarbonyl)cytosine 
• 161599-46-8 (2R,3R,4R,5R)-2-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-5-methyl-tetrahydrofuran-3,4-diyl diacetate 
• 69260-71-5 doxifluridine 
• 76462-82-3 1-(5-Deoxy-2,3-di-O-acetyl-β-D-ribofuranosyl)-5-fluor-uracil 
• 76462-83-4 1-(5-Deoxy-2,3-di-O-acetyl-α-D-ribofuranosyl)-5-fluor-uracil 
• 76462-78-7 1-(5-Desoxy-2,3-O-isopropyliden-α-D-ribofuranosyl)-5-fluor-uracil 
• 76462-79-8 1-(5-Desoxy-α-D-ribofuranosyl)-5-fluor-uracil 
• 37076-71-4 5-deoxy-1,2,3-tri-O-acetyl-D-ribofuranose 
• 13039-71-9 5-deoxy-1-methoxy-D-ribofuranoside 
• 158112-55-1 5-O-deoxy-D-ribofuranose 

Relevant articles and documents

Industrial large-scale production method of capecitabine intermediate

The invention provides an industrial large-scale production method of a capecitabine intermediate. The industrial large-scale production method adopts a one-pot production method of simultaneously adding methanol and acetone, and is a preparation method which is energy-saving, short in production period and high in yield; a method of adding low-boiling-point solvents such as ethyl acetate into dimethyl sulfoxide or pyrrolidone for reflux cooling to take away heat is adopted; and a production method of hydrolyzing while distilling is designed, the methanol and the acetone which are generated byhydrolysis are distilled out, the methanol and the acetone in water are continuously reduced, the reaction is carried out towards K3, and the reaction is complete and thorough.

Preparation method of capecitabine intermediate

The invention discloses a preparation method of a capecitabine intermediate 1, 2, 3-O-triacetyl-5-deoxy-D-furanoside, which belongs to the technical field of medicinal chemistry. According to the invention, D-ribose (a compound I) is used as an initial raw material, and is subjected to a protective group reaction with methanol and acetone under the catalysis of solid acid, 1, 2, 3-hydroxyl is protected to obtain a compound II, then the compound II and thionyl chloride are subjected to a chlorination reaction, hydroxymethyl is changed into chloromethyl, a compound III is obtained, the compoundIII is subjected to a reduction reaction through platinum/carbon catalytic hydrogenation to obtain a compound IV, the compound IV is subjected to acidic hydrolysis to obtain a compound V, and the compound V is subjected to acetylation to obtain a target compound VI. The whole process is short in reaction step and high in economy; side reactions are few, and product purity is high; no wastewater isgenerated in the first three steps, so that the method is more environment-friendly; and the method is beneficial to industrial production of the capecitabine intermediate 1, 2, 3-O-triacetyl-5-deoxy-D-furanoside.

Capecitabine and wherein the intermediate preparation method

The invention discloses a preparation method of capecitabine. The method comprises the following steps: based on D-ribose serving as a starting raw material, carrying out hydroxyl protection, 5-site tosylation, iodine substitution, hypophosphorous acid deiodination and acetylation so as to obtain the key intermediate 12,3-tri-O-acetyl-5-deoxy-beta-D-ribofuranose; carrying out glycosylation on the key intermediate and 5-fluorocytosine; and finally, carrying out N-4 site acylation and deprotection so as to obtain the capecitabine. In the method, a metal catalyst dose not need to be used for participating in reaction, the reaction condition is mild, and the yield is high, thus the method is economical and effective as well as suitable for industrial production on a large scale.

PREPARATION OF CAPECITABINE

The present invention relates to substantially pure capecitabine and processes for the preparation thereof.

HYDROXAMIC ACID DERIVATIVES

The disclosure includes hydroxamic compounds of Formula I: (I) wherein P, Z, and m are defined herein. Also disclosed is a method for treating a neoplastic disease or an immune disease with these compounds.

Benzimidazole 2'-isonucleosides: Design, synthesis, and antiviral activity of 2-substituted-5,6-dichlorobenzimidazole 2'-isonucleosides

2,5,6-Trihalogenated benzimidazole-β-D-ribofuranosyl nucleosides and 2- substituted amino-5,6-dichlorobenzimidazole-β-L-ribofuranosyl nucleosides are potent and selective inhibitors of human cytomegalovirus (HCMV). The D- ribofuranosyl analogs are metabolized rapidly in vivo rendering them unsuitable as drug candidates. The primary source of instability is thought to be the anomeric bond. The synthesis of a series of chemically stable benzimidazole-2'-isonucleosides is presented. The synthetic schemes employed are based on nucleophilic displacements of a 2'-tosylate from carbohydrate intermediates with 2-bromo-5,6-dichlorobenzidazole. 2-Bromo and 2-isopropyl amino analogs with 3'- and 5'-oxo and deoxy substitutions were prepared. The benzimidazole-2'-isonucleosides presented here demonstrated reduced activity against HCMV when compared to other D-ribofuranosyl benzimidazole analogs. In addition, they were not found to be inhibitors of HIV.