54623-25-5

Basic information

• Product Name: 2,3,5-Tri-O-benzyl-D-ribose
• Synonyms: 2,3,5-TRI-O-BENZYL-D-RIBOFURANOSE;TRI-O-BENZYL-D-RIBOFURANOSE;2,3,5-Tri-O-benzyl-D-ribose;2,3,5-TRI-O-BENZYL-D-RIBOFURANOSETRI-O-BENZYL-D-RIBOFURANOSE;(3R,4R,5R)-3,4-bis(benzyloxy)-5-(benzyloxymethyl)tetrahydrofuran-2-ol;D-Ribose,2,3,5-tris-O-(phenylmethyl)-
• CAS NO: 54623-25-5
• Molecular Formula: C₂₆H₂₈O₅
• Molecular Weight: 420.5
• Mol File: 54623-25-5.mol

Chemical Properties

• Boiling Point: 591.5 °C at 760 mmHg
• Flash Point: 197.7 °C
• Appearance: /
• Density: 1.175g/cm³
• Refractive Index: 1.582
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• PKA: 13.28±0.20(Predicted)
• Water Solubility: Sparingly soluble in water.(0.26 g/L) (25°C),
• CAS DataBase Reference: 2,3,5-Tri-O-benzyl-D-ribose(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,5-Tri-O-benzyl-D-ribose(54623-25-5)
• EPA Substance Registry System: 2,3,5-Tri-O-benzyl-D-ribose(54623-25-5)

Safety Data

• Hazardous Substances Data: 54623-25-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2,3,5-Tri-O-benzyl-D-ribose is used as a pharmaceutical intermediate for the synthesis of various biologically active compounds. Its unique structural features allow it to serve as a key building block in the development of novel drugs targeting specific receptors or enzymes.
Used in Chemical Synthesis:
2,3,5-Tri-O-benzyl-D-ribose is used as a synthetic intermediate for the preparation of complex organic molecules, particularly in the field of medicinal chemistry. Its benzyl-protected hydroxyl groups facilitate selective reactions and protect the sugar moiety from unwanted side reactions, making it an ideal candidate for the synthesis of targeted therapeutic agents.
Used in Research and Development:
2,3,5-Tri-O-benzyl-D-ribose is employed as a research tool in the study of carbohydrate chemistry, biochemistry, and molecular biology. Its unique structural properties enable researchers to investigate the role of sugar moieties in various biological processes and their interactions with proteins, lipids, and nucleic acids.
Used in Allosteric Modulation:
2,3,5-Tri-O-benzyl-D-ribose is used as an allosteric enhancer of agonist activity at the A1 adenosine receptor. This application highlights its potential in the development of new therapeutic strategies for conditions such as asthma, chronic obstructive pulmonary disease (COPD), and other respiratory disorders.

InChI:InChI=1/C26H28O5/c27-16-25(30-18-22-12-6-2-7-13-22)26(31-19-23-14-8-3-9-15-23)24(28)20-29-17-21-10-4-1-5-11-21/h1-16,24-26,28H,17-20H2/t24-,25+,26-/m1/s1

Upstream product

• 64363-77-5 methyl 2,3,5-tri-O-benzyl-D-ribofuranoside 

Downstream Products

• 64295-47-2 2,3,5-Tri-O-benzyl-D-ribosehydrazon 
• 14233-62-6 2,3,5-tri-O-benzyl-1-deoxy-D-ribofuranose 

Relevant articles and documents

Oligonucleotides comprising a modified or non-natural nucleobase

One aspect of the present invention relates to a double-stranded oligonucleotide comprising at least one non-natural nucleobase. In certain embodiments, the non-natural nucleobase is difluorotolyl, nitroindolyl, nitropyrrolyl, or nitroimidazolyl. In a preferred embodiment, the non-natural nucleobase is difluorotolyl. In certain embodiments, only one of the two oligonucleotide strands comprising the double-stranded oligonucleotide contains a non-natural nucleobase. In certain embodiments, both of the oligonucleotide strands comprising the double-stranded oligonucleotide independently contain a non-natural nucleobase. In certain embodiments, the oligonucleotide strands comprise at least one modified sugar moiety. Another aspect of the present invention relates to a single-stranded oligonucleotide comprising at least one non-natural nucleobase. In a preferred embodiment, the non-natural nucleobase is difluorotolyl. In certain embodiments, the ribose sugar moiety that occurs naturally in nucleosides is replaced with a hexose sugar, polycyclic heteroalkyl ring, or cyclohexenyl group. In certain embodiments, at least one phosphate linkage in the oligonucleotide has been replaced with a phosphorothioate linkage.