37076-71-4

Basic information

• Product Name: tri-O-acetyl-5-deoxy-D-ribofuranose
• Synonyms: tri-O-acetyl-5-deoxy-D-ribofuranose;5-Deoxy-D-ribofuranose triacetate;1,2,3-Triacety1-5-deoxy-beta-D-ribofuranose;(3R,4R,5R)-5-Methyltetrahydrofuran-2,3,4-triyl triacetate;5-Deoxy-D-ribofuranose 1,2,3-triacetate 1,2,3-Tri-O-acetyl-5-deoxyribose
• CAS NO: 37076-71-4
• Molecular Formula: C₁₁H₁₆O₇
• Molecular Weight: 260.24054
• EINECS: 253-335-1
• Mol File: 37076-71-4.mol
• Article Data: 26

Chemical Properties

• Melting Point: 58-60 °C(Solv: isopropyl ether (108-20-3))
• Boiling Point: 315.3°Cat760mmHg
• Flash Point: 135.7°C
• Appearance: /
• Density: 1.23g/cm³
• Vapor Pressure: 0.00044mmHg at 25°C
• Refractive Index: 1.465
• CAS DataBase Reference: tri-O-acetyl-5-deoxy-D-ribofuranose(CAS DataBase Reference)
• NIST Chemistry Reference: tri-O-acetyl-5-deoxy-D-ribofuranose(37076-71-4)
• EPA Substance Registry System: tri-O-acetyl-5-deoxy-D-ribofuranose(37076-71-4)

Safety Data

• Hazardous Substances Data: 37076-71-4(Hazardous Substances Data)

Usage

General Description

Tri-O-acetyl-5-deoxy-D-ribofuranose is a chemical compound that is derived from ribose, a naturally occurring sugar in the body. It is characterized by three acetyl groups attached to the ribose molecule and the removal of the hydroxyl group from the fifth carbon atom of the ribose ring. This modification results in a more stable and less reactive form of ribose, which has potential applications in various fields such as pharmaceuticals, biochemistry, and organic chemistry. The compound's structure and properties make it suitable for research and development in drug design, as well as for use as a building block in the synthesis of complex molecules. Its stability and solubility also make it a useful tool for studying the structure and function of ribose-containing biomolecules, as well as for the production of new materials and chemicals.

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

• 13039-75-3 5′-deoxyribose 
• 108-24-7 acetic anhydride 
• 23202-81-5 methyl 5-deoxy-2,3-O-isopropylidene-β-D-ribofuranoside 
• 36468-53-8 β-D-ribofuranose 
• 70209-11-9 methyl (1R,2R,3R,4R)-2,3-O-isopropylidene-5-O-trifluoromethanesulfonyl-beta-D-ribofuranoside 
• 52305-57-4 (3aS,4S,6aR)-4-(chloromethyl)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole 
• 158112-53-9 (3aR,6R,6aR)-2,2,6-trimethyltetrahydro-2H-furo(3,4-d)(1,3)dioxol-4-ol 
• 37105-93-4 1,2-O-isopropylidene-5-deoxy-α-D-ribofuranose 
• 32453-67-1 5-deoxy-1,2-O-isopropylidene-α-D-erythro-pentofuranos-3-ulose 
• 37077-81-9 1,2-isopropylidene-α-D-ribofuranose 
• 4099-85-8 methyl 2,3-O-isopropylidene-D-ribofuranoside 
• 20513-96-6 1,2-O-isopropylidene-5-O-p-tolylsulfonyl-α-D-ribofuranose 
• 13039-71-9 5-deoxy-1-methoxy-D-ribofuranoside 
• 50600-40-3 (3aS,4S,6aR)-4-(iodomethyl)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole 

Downstream Products

• 4754-39-6 5'-deoxyadenosine 
• 161599-46-8 (2R,3R,4R,5R)-2-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-5-methyl-tetrahydrofuran-3,4-diyl diacetate 
• 65562-55-2 5'-deoxytoyocamycin 
• 69260-71-5 doxifluridine 
• 27821-07-4 1,2,3-tri-O-acetyl-5-deoxy-β-D-ribofuranose 
• 158112-55-1 5-O-deoxy-D-ribofuranose 
• 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 
• 162204-20-8 N¹-(2',3'-di-O-acetyl-5'-deoxy-β-D-ribofuranosyl)-5-fluoro-N⁴-(pentyloxycarbonyl)cytosine 
• 154361-50-9 capecitabine 
• 76462-82-3 1-(5-Deoxy-2,3-di-O-acetyl-β-D-ribofuranosyl)-5-fluor-uracil 
• 279673-09-5 (2R,3R,4S,5R)-5-methyltetrahydrofuran-2,3,4-triol 
• 93978-94-0 5-deoxy-α-D-ribofuranose 
• 76462-83-4 1-(5-Deoxy-2,3-di-O-acetyl-α-D-ribofuranosyl)-5-fluor-uracil 

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 high-purity capecitabine key intermediate

The invention discloses a preparation method of a high-purity capecitabine key intermediate. The preparation method comprises the following steps: taking D-ribose as an initial raw material, performing hydroxyl protection, 5-site tosylation, reduction, deprotection and acetylation to obtain high-purity 1,2,3-O-triacetyl-5-deoxo-D-ribose, wherein the 5-site tosylation reaction is carried out in anorganic solvent 1 by adopting inorganic base 1. Meanwhile, the acetylation reaction is carried in the presence of alkali 2 by taking water as a reaction solvent and taking 4-dimethylamiopryidine as acatalyst. The preparation method disclosed by the invention is mild in reaction conditions, high in yield, economic and effective, the purity of the prepared 1,2,3-O-triacetyl-5-deoxo-D-ribose can reach 99.0%, the alpha-isomer is small in content even is not detected, and the preparation method is applicable to large-scale industrial production.

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.