160549-10-0

Basic information

• Product Name: 2,3,5-tri-O-benzyl-D-arabinofuranose
• Synonyms: 2,3,5-Tris-O-(phenylmethyl)-D-arabinofuranose
• CAS NO: 160549-10-0
• Molecular Formula: C₂₆H₂₈O₅
• Molecular Weight: 420.49752
• Mol File: 160549-10-0.mol
• Article Data: 17

Chemical Properties

• Boiling Point: 570.5±50.0 °C(Predicted)
• Appearance: /
• Density: 1.21±0.1 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 11.95±0.70(Predicted)
• CAS DataBase Reference: 2,3,5-tri-O-benzyl-D-arabinofuranose(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,5-tri-O-benzyl-D-arabinofuranose(160549-10-0)
• EPA Substance Registry System: 2,3,5-tri-O-benzyl-D-arabinofuranose(160549-10-0)

Safety Data

• Hazardous Substances Data: 160549-10-0(Hazardous Substances Data)

Usage

Description

2,3,5-tri-O-benzyl-D-arabinofuranose is a modified form of D-arabinofuranose, a naturally occurring pentose sugar. It is characterized by the presence of three benzyl groups attached to the 2nd, 3rd, and 5th hydroxyl groups, which significantly alter its chemical properties and reactivity. This modification enhances its stability and utility in various chemical and biological applications.

Uses

Used in Pharmaceutical Industry:
2,3,5-tri-O-benzyl-D-arabinofuranose is used as an intermediate in the synthesis of complex carbohydrate structures and bioactive molecules. Its unique structural features make it a valuable building block for the development of novel pharmaceutical compounds, particularly those targeting carbohydrate-binding proteins or enzymes.
Used in Chemical Synthesis:
In the field of organic chemistry, 2,3,5-tri-O-benzyl-D-arabinofuranose serves as a versatile starting material for the synthesis of various derivatives and analogs. The benzyl protecting groups can be selectively removed or modified, allowing for the introduction of a wide range of functional groups and the creation of diverse chemical libraries.
Used in Research and Development:
This modified sugar is also utilized in academic and industrial research settings to study the role of carbohydrates in biological processes and to develop new methods for carbohydrate synthesis and modification. Its unique properties make it an attractive candidate for exploring the structure-activity relationships of carbohydrate-based compounds and for investigating their interactions with biological targets.
Used in the Synthesis of Phosphono Analogs:
Specifically, 2,3,5-tri-O-benzyl-D-arabinofuranose is used as an intermediate in the synthesis of the phosphono analog of N-acetyl-α-D-mannosamine 1-phosphate from D-arabinose. This phosphono analog has potential applications in the development of antiviral and antibacterial agents, as it may serve as a substrate or inhibitor for key enzymes involved in the biosynthesis of bacterial and viral cell walls.

Upstream product

• 1402833-58-2 S-acetyl-2,3,5-tris-O-(benzyl)-1-thio-β-D-arabinofuranose 
• 62255-44-1 1-O-acetyl-2,3,5-tris-O-(benzyl)-α, β-D-arabinofuranose 
• 10323-20-3 D-Arabinose 
• 100-44-7 benzyl chloride 
• 100-39-0 benzyl bromide 
• 79083-42-4 methyl D-arabinofuranoside 
• 532-20-7 D-arabinofuranose 
• 155931-84-3 (2S,3R,4R)-2,3,5-tri-O-benzyl-4-O-formyl-pentanal 
• 201409-24-7 prop-2-enyl-2',3',5'-tri-O-benzyl-α/β-D-arabinofuranoside 
• 89824-86-2 (2R,3R,4S)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-methoxytetrahydrofuran 

Downstream Products

• 4645-59-4 4-O-Benzoyl-2,3,5-tri-O-benzyl-D-arabinose-diaethyldithioacetal 
• 4263-36-9 2,3,5-Tri-O-benzyl-4-O-p-toluoyl-D-arabinose-diethyldithioacetal 
• 129319-02-4 2,3,5-tri-O-benzyl-1-deoxy-1,1-bis(2-hydroxy-4,5-methylenedioxyphenyl)-D-arabinitol 
• 129926-91-6 2-(2',3',5'-tri-O-benzyl-β-D-arabinofuranosyl)-4,5-methylenedioxyphenol 
• 141062-53-5 Acetic acid (2R,3R)-1,2,4-tris-benzyloxy-3-formyloxy-butyl ester 
• 97204-75-6 (Z)-(2R,3R,4R)-6-methoxy-1,3,4-tribenzyloxy-5-hexen-2-ol 
• 97275-50-8 (E)-(2R,3R,4R)-6-methoxy-1,3,4-tribenzyloxy-5-hexen-2-ol 
• 146346-44-3 methyl (4R,5R,6R)-6-hydroxy-4,5,7-tris(benzyloxy)-2(E)-heptenoate 
• 224952-98-1 (2R,3R,4S,5R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-(octyloxy)tetrahydrofuran 

Relevant articles and documents

Small structure tree alkali compound and its preparation method and application

The invention relates to a Broussonetia kazinoki alkaline compound. Structure of the compound is shown as a formula (1). The invention further provides a preparation method of the compound, a glycosidase inhibitor by using the compound or the compound prepared by the method as an active ingredient and application of the compound or the compound, prepared by the method, serving as an active ingredient in preparing drug. The Broussonetia kazinoki alkaline compound has high glycosidase inhibiting activity and potential medicinal value.

Polyhydroxylated pyrrolidine compound as well as preparation method and application thereof

The invention relates to the field of glycosidase inhibitors and particularly relates to a polyhydroxylated pyrrolidine compound as well as a preparation method and application thereof. The structure of the polyhydroxylated pyrrolidine compound is as shown in formula (I). The polyhydroxylated pyrrolidine compound has high glycosidase inhibition activity and has a potential medicinal value. The formula is as shown in description.

Chemical Synthesis of Ketopentose-5-phosphates

A chemical synthesis of ketopentose-5-phosphates that are involved in the pentose phosphate pathway has been developed. The ketopentose phosphates, d-ribulose-5-phosphate and d-xylulose-5-phosphate, were prepared in five steps starting from known intermed