279673-09-5

Basic information

• Product Name: b-D-Ribofuranose, 5-deoxy-
• Synonyms: (2R,3R,4S,5R)-5-Methyloxolane-2,3,4-triol
• CAS NO: 279673-09-5
• Molecular Formula: C₅H₁₀O₄
• Molecular Weight: 134.1305
• Mol File: 279673-09-5.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 277.7°Cat760mmHg
• Flash Point: 121.7°C
• Density: 1.478g/cm³
• CAS DataBase Reference: b-D-Ribofuranose, 5-deoxy-(CAS DataBase Reference)
• NIST Chemistry Reference: b-D-Ribofuranose, 5-deoxy-(279673-09-5)
• EPA Substance Registry System: b-D-Ribofuranose, 5-deoxy-(279673-09-5)

Safety Data

• Hazardous Substances Data: 279673-09-5(Hazardous Substances Data)

Upstream product

• 52305-57-4 (3aS,4S,6aR)-4-(chloromethyl)-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 
• 78341-97-6 1-O-methyl-2,3-O-isopropylidene-5-deoxy-D-ribofuranose 
• 50610-99-6 1-O-methyl-2,3-O-isopropylidene-5-O-(methanesulfonyl)-β-D-ribofuranoside 
• 4099-85-8 ((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol 
• 36468-53-8 β-D-ribofuranose 
• 23202-81-5 methyl 5-deoxy-2,3-O-isopropylidene-β-D-ribofuranoside 
• 4137-56-8 methyl 2,3-O-isopropylidene-5-O-p-tolylsulfonyl-β-D-ribofuranoside 
• 27821-07-4 1,2,3-tri-O-acetyl-5-deoxy-β-D-ribofuranose 
• 132064-84-7 5-deoxy-2,3-O-isopropylidene-D-ribofuranose 

Downstream Products

• 27821-07-4 1,2,3-tri-O-acetyl-5-deoxy-β-D-ribofuranose 
• 154361-50-9 capecitabine 
• 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 

Relevant articles and documents

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.

Safe and Alternate Process for the Reductions of Methanesulfonates: Application in the Synthesis of 1,2,3-Triacetyl-5-deoxy-d-ribofuranoside

Diethylene glycol dimethyl ether, diglyme, and 1,2-bis(2-methoxyethoxy)ethane, triglyme, are found to be suitable and safe alternate solvents to DMSO for the reduction of methanesulfonate in sodium borohydride. Addition of anhydrous lithium chloride led to the complete reduction of methanesulfonate esters to the corresponding alkanes in the presence of sodium borohydride in these solvents (diglyme and triglyme). This protocol is useful in the preparation of 1,2,3-triacetyl-5-deoxy-d-ribofuranoside, 7, a key intermediate of Capecitabine, 1, on the commercial scale.

PYRAZOLO[3, 4-D]PYRIMIDINE DERIVATIVES AS ANTIBACTERIAL COMPOUNDS

This invention relates to 6-oxy-4-amino-1-(tetrahydrofuranyl)-1H- pyrazolo[3,4-d]pyrimidin-3(2H)-ones in free or salt form, e.g., compounds of formula (I) and formula (II) their use, e.g., in the treatment of bacterial infections and the process of preparing said compounds.