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

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

• 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 
• 108-24-7 acetic anhydride 
• 532-20-7 D-Ribose 
• 67-64-1 acetone 
• 58-63-9 Inosine 
• 64-19-7 acetic acid 
• 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 
• 13039-71-9 5-deoxy-1-methoxy-D-ribofuranoside 

Downstream Products

• 279673-09-5 (2R,3R,4S,5R)-5-methyltetrahydrofuran-2,3,4-triol 
• 93978-94-0 5-deoxy-α-D-ribofuranose 
• 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 
• 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.

AMPHIPHILE PRODRUGS

Amphiphilic prodrugs of general formula A-X are disclosed, wherein A is a biologically active agent or may be metabolised to a biologically active agent; and X is selected from the group consisting of R, or up to three R moieties attached to a linker, Y1, Y2 or Y3, wherein R is selected from a group consisting of alkyl, alkenyl, alkynyl, branched alkyl, branched alkenyl, branched alkynyl, substituted alkyl, substituted alkenyl and substituted alkynyl groups and their analogues; Y1 is a linker group which covalently attached to an R group at one site and is attached to A at a further independent site; Y2 is a linker group which is covalently attached to two R groups at two independent sites and is attached to A at a further independent site; and Y3 is a linker group which is covalently attached to three R groups at three independent sites and is attached to A at a further independent site. Self-assembly of the amphiphilic prodrugs into reverse lyotropic phases, particularly hexagonal, cubic and sponge, is disclosed. In preferred embodiments A is dopamine or a 5-fluorouracil prodrug.

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.

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.

Method for preparing 1,2,3-tris-O-acetyl-5-deoxy-beta-D-ribose

The invention discloses a method for preparing 1,2,3-tris-O-acetyl-5-deoxy-beta-D-ribose and belongs to the field of nucleoside synthesis in organic chemistry. The method comprises the following reaction steps: reacting inosine and halogenated sulfoxide to obtain a compound 2; reducing the compound 2 at lithium metal, and adding ammonium hydroxide for deprotection so as to obtain a compound 3; reacting the compound 3 in acetic anhydride under catalysis of inorganic boric acid, thereby obtaining the 1,2,3-tris-O-acetyl-5-deoxy-beta-D-ribose. The synthetic method is cheap in raw materials, shortin steps and easy for industrial production and has industrial application prospects.

Preparation method of 1,2,3-tri-O-acetyl-5-deoxy-beta-D-ribose

The invention discloses a preparation method of 1,2,3-tri-O-acetyl-5-deoxy-beta-D-ribose, which belongs to the field of nucleoside medicine synthesis. The reaction steps of the preparation method areas follows: inosine reacts as a raw material with organic boronic acid to protect 2' and 3' hydroxyl groups, room-temperature reduction is then carried out under the condition of potassium borohydrideand trifluoroacetic acid, diol exchange deprotection is then carried out, and finally, acetic anhydride is added for reflux reaction, so that the 1,2,3-tri-O-acetyl-5-deoxy-beta-D-ribose is obtained.The synthesis method has the advantages of easy obtainment of the raw material, short steps and high process safety, and has an industrial application prospect.

Preparation method of 1,2,3-tri-O-acetyl-5-deoxy-beta-D-ribose

The invention discloses a preparation method of 1,2,3-tri-O-acetyl-5-deoxy-beta-D-ribose, and belongs to the field of nucleoside synthesis in organic chemistry. The method comprises reaction steps asfollows: inosine 1 and triphenyl phosphite-halogen are subjected to a reaction, and a compound 2 is obtained; then the compound 2 is subjected to hydrogenation reduction under palladium/carbon catalysis; an obtained compound 3 is subjected to a reaction in acetic anhydride under catalysis of inorganic boric acid, and 1,2,3-tri-O-acetyl-5-deoxy-beta-D-ribose is obtained. The synthesis method adoptscheap raw materials and short steps and has industrial application prospect, and industrial production is easy.

Synthetic method of 1,2,3-tri-O-acetyl-5-deoxy-D ribose

The invention provides a synthetic method of 1,2,3-tri-O-acetyl-5-deoxy-D ribose. The synthetic method comprises the steps of with D ribose as a starting raw material, protecting a site 1 of D ribose by virtue of isopropyl, protecting sites 2 and 3 by virtue of propylidene, removing 5-site hydroxyl through reduction, carrying out deprotection on the sites 2 and 3, and carrying out acetylation, so as to obtain a target product. The total yield of the route is 64% and is greatly superior to that of a traditional process, and particularly, the final product is a pure beta isomer and is easily recrystallized, purified and produced in a large scale.

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.