27821-07-4

Basic information

• Product Name: (2S,3R,4R,5R)-5-methyltetrahydrofuran-2,3,4-triyl triacetate
• Synonyms: beta-D-5-Deoxyxylofuranose triacetate;(2S,3R,4S,5R)-5-Methyltetrahydrofuran-2,3,4-triyl triacetate;2-D-5-Deoxy-xylofuranose Triacetate
• CAS NO: 27821-07-4
• Molecular Formula: C₁₁H₁₆O₇
• Molecular Weight: 260
• EINECS: -0
• Mol File: 27821-07-4.mol
• Article Data: 19

Chemical Properties

• Boiling Point: 315℃
• Flash Point: 136℃
• Appearance: /
• Density: 1.23
• CAS DataBase Reference: (2S,3R,4R,5R)-5-methyltetrahydrofuran-2,3,4-triyl triacetate(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3R,4R,5R)-5-methyltetrahydrofuran-2,3,4-triyl triacetate(27821-07-4)
• EPA Substance Registry System: (2S,3R,4R,5R)-5-methyltetrahydrofuran-2,3,4-triyl triacetate(27821-07-4)

Safety Data

• Hazardous Substances Data: 27821-07-4(Hazardous Substances Data)

Usage

Uses

β-D-5-Deoxy-xylofuranose Triacetate is used in the synthesis of nucleotide derivatives. Primarily studied in the understanding of long range σ-coupling properties.

Upstream product

• 108-24-7 acetic anhydride 
• 23202-81-5 methyl 5-deoxy-2,3-O-isopropylidene-β-D-ribofuranoside 
• 4099-85-8 ((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol 
• 279673-09-5 (2R,3R,4S,5R)-5-methyltetrahydrofuran-2,3,4-triol 
• 78341-98-7 Methyl-(5-desoxy-2,3-di-O-acetyl-D-ribofuranosid) 
• 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 
• 78341-97-6 1-O-methyl-2,3-O-isopropylidene-5-deoxy-D-ribofuranose 
• 532-20-7 D-Ribose 
• 4099-85-8 methyl 2,3-O-isopropylidene-D-ribofuranoside 
• 4137-56-8 ((3aR,4R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl 4-methylbenzenesulfonate 
• 64-19-7 acetic acid 
• 52305-57-4 (3aS,4S,6aR)-4-(chloromethyl)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole 
• 108-22-5 Isopropenyl acetate 

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 
• 124012-42-6 5'-deoxy-5-fluoro-N⁴-(3,4,5-trimethoxybenzoyl)cytidine 
• 154361-50-9 capecitabine 
• 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 
• 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 
• 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 

Relevant articles and documents

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.

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.

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.