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
• Article Data: 7

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

Description

Methyl-5-deoxy-2,3-O-isopropylidene-D-ribofuranoside, also known as 5-Deoxy-2,3-O-(1-methylethylidene)-D-ribofuranoside Methyl Ether, is a chemical compound that serves as an intermediate in the synthesis of Capecitabine-related compounds. It is a modified form of D-ribofuranoside, with a methyl group and an isopropylidene protecting group attached to the 2,3-O position, and the 5-O position is deoxylated.

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

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

Downstream Products

• 5531-24-8 L-5-deoxy-lyxose 
• 158112-55-1 5-O-deoxy-D-ribofuranose 
• 13039-71-9 5-deoxy-1-methoxy-D-ribofuranoside 
• 37076-71-4 5-deoxy-1,2,3-tri-O-acetyl-D-ribofuranose 
• 76462-79-8 1-(5-Desoxy-α-D-ribofuranosyl)-5-fluor-uracil 
• 76462-78-7 1-(5-Desoxy-2,3-O-isopropyliden-α-D-ribofuranosyl)-5-fluor-uracil 
• 76462-83-4 1-(5-Deoxy-2,3-di-O-acetyl-α-D-ribofuranosyl)-5-fluor-uracil 
• 76462-82-3 1-(5-Deoxy-2,3-di-O-acetyl-β-D-ribofuranosyl)-5-fluor-uracil 
• 69260-71-5 doxifluridine 
• 161599-46-8 (2R,3R,4R,5R)-2-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-5-methyl-tetrahydrofuran-3,4-diyl diacetate 
• 162204-20-8 N¹-(2',3'-di-O-acetyl-5'-deoxy-β-D-ribofuranosyl)-5-fluoro-N⁴-(pentyloxycarbonyl)cytosine 
• 154361-50-9 capecitabine 
• 27821-07-4 1,2,3-tri-O-acetyl-5-deoxy-β-D-ribofuranose 
• 1236199-88-4 C₁₇H₂₅FN₄O₈ 

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.

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.