96291-75-7

Basic information

• Product Name: 1,3,5-Tri-O-acetyl-2-deoxy-beta-D-erythro-pentofuranose
• Synonyms: 1,3,5-TRI-O-ACETYL-2-DEOXY-BETA-D-ERYTHRO-PENTOFURANOSE;B-D-ERYTHRO-PENTOFURANOSE;(2S,4S,5R)-5-(Acetoxymethyl)tetrahydrofuran-2,4-diyl diacetate
• CAS NO: 96291-75-7
• Molecular Formula: C₁₁H₁₆O₇
• Molecular Weight: 260.24
• Mol File: 96291-75-7.mol
• Article Data: 15

Chemical Properties

• Boiling Point: 329.297 °C at 760 mmHg
• Flash Point: 142.967 °C
• Appearance: /
• Density: 1.24 g/cm³
• Refractive Index: 1.466
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 1,3,5-Tri-O-acetyl-2-deoxy-beta-D-erythro-pentofuranose(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3,5-Tri-O-acetyl-2-deoxy-beta-D-erythro-pentofuranose(96291-75-7)
• EPA Substance Registry System: 1,3,5-Tri-O-acetyl-2-deoxy-beta-D-erythro-pentofuranose(96291-75-7)

Safety Data

• Hazardous Substances Data: 96291-75-7(Hazardous Substances Data)

Usage

General Description

1,3,5-Tri-O-acetyl-2-deoxy-beta-D-erythro-pentofuranose is a chemical compound with a complex name that belongs to the class of carbohydrates. It is a derivative of the sugar molecule D-erythro-pentofuranose, which is a component of nucleic acids and many other important biological molecules. The compound is acetylized at three positions and contains a deoxy group, making it a modified form of the natural sugar. This chemical is often used in organic synthesis and as a building block for the preparation of other complex molecules. Its structure and properties make it a valuable tool in the study of carbohydrate chemistry and as a potential drug target in medicinal chemistry.

InChI:InChI=1/C11H16O7/c1-6(12)15-5-10-9(16-7(2)13)4-11(18-10)17-8(3)14/h9-11H,4-5H2,1-3H3/t9-,10+,11+/m0/s1

Upstream product

• 533-67-5 2-Deoxy-D-ribose 
• 108-24-7 acetic anhydride 
• 51255-17-5 1-O-methyl-2-deoxy-D-ribofuranoside 
• 151767-35-0 3,5-di-O-acetyl-2-deoxy-α/β-D-ribofuranoside 
• 452-51-7 D-2-deoxyribose 
• 36792-88-8 2-deoxy-D-ribose 

Downstream Products

• 6979-97-1 3',5'-diacetylthymidine 
• 3056-17-5 stavudin 
• 7481-90-5 3',4'-anhydrothymidine 
• 50-89-5 thymidine 
• 1254186-96-3 1-(3,5-di-O-acetyl-2-deoxy-D-ribofuranosyl)-5-azacytosine 
• 22432-93-5 4-amino-1-(O³,O⁵-diacetyl-β-D-erythro-2-deoxy-pentofuranosyl)-1H-[1,3,5]triazin-2-one 
• 22432-93-5 3',5'-O-acetyl-2'-deoxy-5-azacytidine 
• 22969-05-7 1-(4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-2-one 
• 1402737-97-6 p-tolyl-3,5-di-O-acetyl-1-thio-2-deoxy-α-D-ribofuranoside 
• 1402737-50-1 p-tolyl-3,5-di-O-acetyl-1-thio-2-deoxy-β-D-ribofuranoside 
• 367518-79-4 C₅₅H₆₆N₇O₁₇PSi 
• 367518-81-8 6-[2’-deoxy-3’-O-dimethoxytrityl-α-D-ribofuranose-1’-yl]amino-5-nitro-2-(phenoxylacetyl)amino-3H-pyrimidine-4-one 
• 367518-78-3 6-[2’-deoxy-3’-O-dimethoxytrityl-β-D-ribofuranose-1’-yl]amino-5-nitro-2-(phenoxylacetyl)amino-3H-pyrimidine-4-one 

Relevant articles and documents

SYNTHESIS AND IMPROVEMENT OF A NUCLEOSIDE ANALOGUE AS AN ANTI-CANCER AND ANTI-VIRAL DRUG

The invention is a drug for anticancer and antiviral therapy, comprising a nucleoside analogue (7) comprising a furan ring irreversibly bound to the RNA/DNA synthesis chain by phosphodiester bonds and having SP3 hybridization, and folic acid (A) bound to the nucleoside analogue (7) comprising furan ring. The synthesis method of the said nucleoside analogue is also contained within the scope of the invention. In this work, a nucleoside-analogue was transformed after converting the furan-ring hybridization from Sp2 to Sp3 to make it more selectivity with different enzymes and linking it via site 5 with the effective folic acid towards entering the substances inside the cells and to become the final compound possessing anti-cancer and anti- virus properties after controlling the replication and reproduction process in DNA.

First characterisation of two important postulated intermediates in the formation of a HydT DNA lesion, a thymidine oxidation product

A number of environmental pollutants and endogenous oxidation agents form 1-(2-deoxy-β-d-ribofuranosyl)-5-hydroxy-5-methylhydantoin (HydT), an important DNA lesion resulting from thymidine oxidation. In this paper, two intermediates, postulated in the formation of HydT, have been characterised for the first time. The first, N1-formyl-N3-pyruvoylurea intermediate, was produced by the ozonolysis reaction of 2′,3′,5′-tri-O-acetylribo-, 3′,5′-di-O-TBS- and N3,O3′,O5-tribenzyl-protected thymidines and was shown to produce, upon decomposition and depending on the protecting group and the conditions, HydT alone, or together with protected-β-d-ribofuranosyl-N1-formylurea and formamide products. In addition, the second and long sought, open-chain-pyruvoylurea intermediate, was produced through de novo synthesis in protected β-d-ribofuranosyl-, 2-deoxy-β-d-ribofuranosyl- and 2-deoxy-β-d-ribopyranosyl systems. The conditions that induce the cyclization to the hydantoin ring of HydT have been determined. The chemistry utilised in the de novo synthesis is suitable for generating isotopically labelled HydT, as a reference in isotope-dilution-aided quantification of DNA damage.

Sono-transition-metal catalysis of one-pot three-step synthesis of glycosyl-1,2,3-triazoles

As a continuation of our studies directed at the development of straightforward and sustainable methodologies, we describe herein an original example of a combined effect of ultrasonic activation and iron-copper dual catalysis that allows an efficient and ecofriendly one-pot, three-step route to a new series of nucleoside-substituted triazoles. The reactions were carried out under both conventional and ultrasonic irradiation conditions. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications to view the free supplemental file.