21740-23-8

Basic information

• Product Name: 1-Chloro-3,5-di-(4-chlorobenzoyl)-2-deoxy-D-ribose
• Synonyms: 3,5-bis[o-(p-chlorbenzoyl)]-alpha-D-ribofuranosyl chloride;1-Cl-3,5-bis-(4-cl-bz)- 2-deoxy-D-ribofuranose;1-Chloro-3,5-bis-(4-chlorobenzoyl)-2-deoxy-D-ribofuranose;[5-Chloro-2-[(4-chlorobenzoyl)oxymethyl]oxolan-3-yl] 4-chlorobenzoate;1-Chloro-3,5-di-(4-chlorobenzoyl)-2-deoxy-D-ribose;(4S,5R)-2-chloro-4-benzoyloxy-5-(benzoyloxymethyl)tetrahydrofuran;1-α-Chloro-3,5-di-O-(4-chlorobenzoyl) -2-deoxy-D-ribofuranose;(2R,3S,4R,5R)-5-Chloro-2-((4-chlorobenzoyloxy)methyl)-4-hydroxytetrahydrofuran-3-yl 4-chlorobenzoate
• CAS NO: 21740-23-8
• Molecular Formula: C₁₉H₁₅Cl₃O₅
• Molecular Weight: 429.68
• EINECS: 2017-001-1
• Product Categories: Bases & Related Reagents;Intermediates;Nucleotides
• Mol File: 21740-23-8.mol

Chemical Properties

• Melting Point: 110-118°C (dec.)
• Boiling Point: 530.6 °C at 760 mmHg
• Flash Point: 193 °C
• Appearance: White solid
• Density: 1.46 g/cm³
• Vapor Pressure: 1.5E-19mmHg at 25°C
• Refractive Index: 1.636
• Storage Temp.: Hygroscopic, -20?C Freezer, Under Inert Atmosphere
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
• Stability: Not stable in Solution
• CAS DataBase Reference: 1-Chloro-3,5-di-(4-chlorobenzoyl)-2-deoxy-D-ribose(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Chloro-3,5-di-(4-chlorobenzoyl)-2-deoxy-D-ribose(21740-23-8)
• EPA Substance Registry System: 1-Chloro-3,5-di-(4-chlorobenzoyl)-2-deoxy-D-ribose(21740-23-8)

Safety Data

• Hazardous Substances Data: 21740-23-8(Hazardous Substances Data)

Usage

Uses

1. Used in Pharmaceutical Industry:
1-Chloro-3,5-di-(4-chlorobenzoyl)-2-deoxy-D-ribose is used as an intermediate in the synthesis of nucleotide analogs for the pharmaceutical industry. Its application is crucial in the development of new drugs targeting various diseases, including cancer and viral infections.
2. Used in Research and Development:
Due to its instability in solution, 1-Chloro-3,5-di-(4-chlorobenzoyl)-2-deoxy-D-ribose is also used in research and development settings to study its properties, reactivity, and potential applications in the synthesis of other bioactive compounds.

InChI:InChI=1/C19H15Cl3O6/c20-12-5-1-10(2-6-12)15(24)16(25)18(27)19(28,9-14(22)23)17(26)11-3-7-13(21)8-4-11/h1-8,16,18,25,27-28H,9H2/t16?,18-,19-/m1/s1

Upstream product

• 452-51-7 D-2-deoxyribose 
• 122-01-0 4-chloro-benzoyl chloride 
• 51255-17-5 1-O-methyl-2-deoxy-D-ribofuranoside 
• 80339-59-9 methyl 3,5-dibenzoyloxy-2-deoxy-α-D-erythropentofuranoside 

Downstream Products

• 136743-09-4 5-benzylthio-1-(3,5-di-O-p-chlorobenzoyl-2-deoxy-β-D-ribofuranosyl)-1,2-dihydro-2-oxopyrazine 
• 136743-10-7 5-benzylthio-1-(3,5-di-O-p-chlorobenzoyl-2-deoxy-α-D-ribofuranosyl)-1,2-dihydro-2-oxopyrazine 
• 96245-83-9 1-<3,5-bis-O-(p-chlorobenzoyl)-2-deoxy-β-D-ribofuranosyl>-5-bromo-2-pyrimidinone 
• 96245-85-1 C₂₃H₁₇BrCl₂N₂O₆ 
• 96245-84-0 1-<3,5-bis-O-(p-chlorobenzoyl)-2-deoxy-β-D-ribofuranosyl>-5-iodo-2-pyrimidinone 
• 96245-86-2 ((2R,3S,5S)-3-((4-chlorobenzoyl)oxy)-5-(5-iodo-2-oxopyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)methyl 4-chlorobenzoate 
• 126200-05-3 C₂₄H₁₉Cl₂N₅O₅ 
• 156419-96-4 1-<3,5-di-O-(4-chlorobenzoyl)-2-deoxy-β-D-ribofuranosyl>-5-ethyl-2-pyrimidinone 
• 156419-95-3 1-<3,5-di-O-(4-chlorobenzoyl)-2-deoxy-α-D-ribofuranosyl>-5-ethyl-2-pyrimidinone 
• 129664-47-7 1-<3,5-bis-O-(p-chlorobenzoyl)-2-deoxy-β-D-erythro-pentofuranosyl>-5-trifluoromethyluracil 
• 129664-48-8 1-<3,5-bis-O-(p-chlorobenzoyl)-2-deoxy-α-D-erythro-pentofuranosyl>-5-trifluoromethyluracil 
• 5173-91-1 3',5'-O-bis(4-chlorobenzoyl)-2'-deoxy-β-D-uridine 
• 4449-30-3 1-[O³,O⁵-bis-(4-chloro-benzoyl)-α-D-erythro-2-deoxy-pentofuranosyl]-1H-pyrimidine-2,4-dione 
• 4449-32-5 3',5'-di-O-(p-chlorobenzoyl)-β-D-thymidine 

Relevant articles and documents

PROCESSES FOR PRODUCING DECITABINE

New processes for producing decitabine are provided.

Synthesis of 1-(2-deoxy-β-D-ribofuranosyl)-2,4-difluoro-5- substituted-benzene thymidine mimics, some related α-anomers, and their evaluation as antiviral and anticancer agents

A group of unnatural 1-(2-deoxy-β-D-ribofuranosyl)-2.4-difluorobenzenes having a variety of C-5 substituents (H, Me, F, Cl, Br, I, CF3, CN, NO2, NH2), designed as thymidine mimics, were synthesized for evaluation as anticancer and antiviral agents. The coupling reaction of 3,5-bis-O-(p-chlorobenzoyl) 2-deoxy-α-D-ribofuranosyl chloride with an organocadmium reagent [(2,4-difluorophenyl)2Cd] afforded a mixture of the α- and β-anomeric products (α:β = 3:1 to 10:1 ratio). Treatment of the α-anomer with BF3·Et2O in nitroethane at 110-120°C for 30 min was developed as an efficient method for epimerization of the major α-anomer to the desired β-anomer. The 5-substituted (H, Me, Cl, I, NH2) β-anomers exhibited negligible cytotoxicity in a MTT assay (CC50 = 10-3-10-4 M range), relative to thymidine (CC50 = 10-3-10-5 M range), against a variety of cancer cell lines. In contrast, the 5-NO2 derivative was more cytotoxic (CC50 = 10-5-10-6 M range). A number of 5-substituted β-anomers, and some related α-anomers, that were evaluated using a wide variety of antiviral assay systems [HSV-1, HSV-2, varicella-zoster virus (VZV), vaccinia virus, vesicular stomatitis, cytomegalovirus (CMV) and human immunodeficiency (HIV-1, HIV-2) viruses], showed that this class of unnatural C-aryl nucleoside mimics are inactive antiviral agents.

Synthesis and hybridization studies of oligonucleotide sequences with modified fluorescent nucleoside analogs

Two complementary oligodeoxynucleotide hexamers CATGAA and TTCATG and a pentamer with a fluorescent nucleoside analog viz. 9-N-(2'-deoxy-β-D- ribofuranosyl) carbazole (C*) incorporated into it, TTC*ATG were synthesized and characterised by spectroscopic and chromatographic studies. The comparative fluorescent studies of the two nucleoside analogs viz. 9-N- (2'-deoxy-β-D-ribofuranosyl) acridone and its carbazole analog (C*) have been carried out under different experimental conditions. The effect on fluorescence by incorporation of (C*) into the sequence and its subsequent hybridization with the complementary sequence have been studied.

Process for Producing 1-(2'-deoxy-beta-D-erythropentofuranosyl)-5-trifluoromethyluracil Derivatives

A process for producing 1-(2'-deoxy-β-D-erythro-pentofuranosyl)-5-trifluoromethyluracil derivative of the formula (3) by which the desired compound can be produced easily at a low cost with high selectivity is disclosed. The process according to the present invention comprises (a) reacting 5-trifluoromethyl-5,6-dihydrouracil with alkylsulfoxide in the presence of a halogen and an acid catalyst to obtain 5-trifluoromethyluracil; (b) reacting the obtained 5-trifluoromethyluracil with a silylating agent to obtain 5-trifluoromethyl-2,4-bis(trimethylsilyloxy)pyrimidine of the formula (1) and (c) reacting the obtained 5-trifluoromethyl-2,4-bis(trimethylsilyloxy)pyrimidine with 2-deoxy-α-D-erythro-pentofuranosyl halide derivative of the formula (2) in chloroform solvent in the presence of fluoride ion and in the presence of a copper compound as a catalyst.