62211-93-2

Basic information

• Product Name: 1,2,3-Triacetyl-5-deoxy-D-ribose
• Synonyms: 1,2,3-Triacetyl-5-deoxy-D-ribose;5-Deoxy-b-D-ribofuranose triacetate;1,2,3-Triacetoxy-5-Deoxy Ribose;1,2,3-Triacetoxy-5-Deoxy-Beta-D-Ribofuranose;1,2,3-Tri-O-acetyl-5-deoxy-b-D-ribofuranose;1,2,6-TRI-O-ACETYL-3,4-DI-O-BENZYL-ALPHA-D-MANNOPYRANOSE;5-Deoxy-b-D-ribofuranose;ACETYLFURANOSIDE
• CAS NO: 62211-93-2
• Molecular Formula: C₁₁H₁₆O₇
• Molecular Weight: 260.24
• EINECS: 2017-001-1
• Product Categories: Antineoplastic drug, 5-FU analog;Carbohydrates & Derivatives;Intermediates;Capecitabine intermediate
• Mol File: 62211-93-2.mol
• Article Data: 19

Chemical Properties

• Melting Point: 63-64°C
• Boiling Point: 315°C
• Flash Point: 136°C
• Appearance: Yellow to Brown/Powder
• Density: 1.23
• Vapor Pressure: 0.00044mmHg at 25°C
• Refractive Index: 1.465
• Storage Temp.: Refrigerator
• Solubility: Soluble in ethanol
• CAS DataBase Reference: 1,2,3-Triacetyl-5-deoxy-D-ribose(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,3-Triacetyl-5-deoxy-D-ribose(62211-93-2)
• EPA Substance Registry System: 1,2,3-Triacetyl-5-deoxy-D-ribose(62211-93-2)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 62211-93-2(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

Intermediate in the preparation of Cepecitabine.

InChI:InChI=1/C11H16O7/c1-5-9(16-6(2)12)10(17-7(3)13)11(15-5)18-8(4)14/h5,9-11H,1-4H3/t5-,9-,10-,11+/m1/s1

Upstream product

• 36468-53-8 β-D-ribofuranose 
• 108-24-7 acetic anhydride 
• 64-19-7 acetic acid 
• 52305-57-4 (3aS,4S,6aR)-4-(chloromethyl)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole 
• 23202-81-5 methyl 5-deoxy-2,3-O-isopropylidene-β-D-ribofuranoside 
• 108-22-5 Isopropenyl acetate 
• 158112-55-1 5-O-deoxy-D-ribofuranose 
• 532-20-7 D-Ribose 
• 67-64-1 acetone 
• 58-63-9 Inosine 
• 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 
• 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 

Downstream Products

• 161599-46-8 (2R,3R,4R,5R)-2-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-5-methyl-tetrahydrofuran-3,4-diyl diacetate 
• 154361-50-9 capecitabine 
• 279673-09-5 (2R,3R,4S,5R)-5-methyltetrahydrofuran-2,3,4-triol 
• 93978-94-0 5-deoxy-α-D-ribofuranose 
• 69260-71-5 doxifluridine 
• 76462-82-3 1-(5-Deoxy-2,3-di-O-acetyl-β-D-ribofuranosyl)-5-fluor-uracil 
• 162204-20-8 N¹-(2',3'-di-O-acetyl-5'-deoxy-β-D-ribofuranosyl)-5-fluoro-N⁴-(pentyloxycarbonyl)cytosine 
• 161599-31-1 Acetic acid (2R,3R,4R,5R)-4-acetoxy-2-[5-fluoro-2-oxo-4-(3,4,5-trimethoxy-benzoylamino)-2H-pyrimidin-1-yl]-5-methyl-tetrahydro-furan-3-yl ester 
• 162204-19-5 Acetic acid (2R,3R,4R,5R)-4-acetoxy-2-(4-butoxycarbonylamino-5-fluoro-2-oxo-2H-pyrimidin-1-yl)-5-methyl-tetrahydro-furan-3-yl ester 
• 124012-42-6 5'-deoxy-5-fluoro-N⁴-(3,4,5-trimethoxybenzoyl)cytidine 

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.

A three-acetyl deoxyribose α isomer preparation method

The invention discloses a capecitabine intermediate impurity tri acetyl deoxyribose α isomer: the chemical name is 1 α - 1, 2, 3 - three-acetoxy - 5 - deoxy - D - ribose of the preparation method. The preparation method in order to 5 - deoxy - D - ribose as a synthetic raw material, by isopropenyl acetate/iron trichloride acetylation than three acetyl deoxyribose α isomer crude, passes through the column again chromatography purification to obtain the triacetyl deoxyribose α isomer pure product. The invention provides a triacetyl deoxyribose α isomer preparation method, with simple operation, the advantage of the high product purity, for capecitabine intermediate and the quality of the finished good foundation for the study.

3-Trifluoromethylpyrazolones derived nucleosides: Synthesis and antiviral evaluation

Dengue (DENV) viral infection is a global public health problem that infrequently develops life threatening diseases such as dengue hemorrhagic fever (DFS) and dengue shock syndrome (DSS). Middle East respiratory syndrome coronavirus (MERS-CoV) is a highly pathogenic human corona virus with 38% fatality rate of infected patients. A series of 4-arylhydrazono-5-trifluoromethyl-pyrazolones, their ribofuranosyl, and 5′-deoxyribofuranosyl nucleosides were synthesized, geometry optimized using Density functional theory (DFT), and evaluated for their antiviral activity. 2-Nitrophenylhydrazonopyra-zolone derivative 5 showed significant activity against MERS-CoV (EC50 = 4.6 μM). The nucleoside analog 8 showed moderate activity against DENV-2 (EC50 = 10 μM), while the activity was abolished with the corresponding 5′-deoxyribonucleoside analogs. The identified hits in this study set this category of compounds for further future optimizations.