1226-39-7

Basic information

• Product Name: 4-NITROPHENYL-BETA-D-FUCOPYRANOSIDE
• Synonyms: 4-NITROPHENYL-BETA-D-FUCOPYRANOSIDE;4-NITROPHENYL-BETA-D-FUCOSE;P-NITROPHENYL BETA-D-FUCOPYRANOSIDE;P-NITROPHENYL-BETA-D-FUCOSIDE;P-NITROPHENYL-ALPHA-D-FUCOSIDE;PNP-BETA-D-FUC;P-NITROPHENYL B-D-FUCOPYRANOSIDE;4-nitrophenyl β-d-fuco-pyran-oside
• CAS NO: 1226-39-7
• Molecular Formula: C₁₂H₁₅NO₇
• Molecular Weight: 285.25
• EINECS: 1533716-785-6
• Product Categories: Sugars, Carbohydrates & Glucosides;Biochemistry;Fucose;Glycosides;Sugars;Enzyme Substrates;Fucosidase, alpha-L-;Glycosidase, beta;ChromogenicEnzyme Substrates;Fucoside;Substrates;Substrates by Enzyme;substrate
• Mol File: 1226-39-7.mol
• Article Data: 3

Chemical Properties

• Melting Point: 191-192 °C
• Boiling Point: 515.4oC at 760 mmHg
• Flash Point: 265.5oC
• Appearance: /
• Density: 1.503g/cm3
• Vapor Pressure: 1.9E-11mmHg at 25°C
• Refractive Index: -75 ° (C=1, EtOH)
• Storage Temp.: −20°C
• PKA: 12.68±0.70(Predicted)
• BRN: 1291394
• CAS DataBase Reference: 4-NITROPHENYL-BETA-D-FUCOPYRANOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-NITROPHENYL-BETA-D-FUCOPYRANOSIDE(1226-39-7)
• EPA Substance Registry System: 4-NITROPHENYL-BETA-D-FUCOPYRANOSIDE(1226-39-7)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• F: 10
• Hazardous Substances Data: 1226-39-7(Hazardous Substances Data)

Usage

Description

4-NITROPHENYL-BETA-D-FUCOPYRANOSIDE, with the CAS number 1226-39-7, is a synthetic compound that plays a significant role in organic synthesis. It is a derivative of fucopyranosides, which are a type of sugar molecule commonly found in various biological systems. 4-NITROPHENYL-BETA-D-FUCOPYRANOSIDE is characterized by its unique chemical structure, which includes a nitrophenyl group and a beta-D-Fucopyranosyl moiety, making it a versatile building block for the development of various chemical and pharmaceutical products.

Uses

Used in Organic Synthesis:
4-NITROPHENYL-BETA-D-FUCOPYRANOSIDE is used as a key intermediate in the synthesis of complex organic molecules, particularly those involving fucopyranosides. Its unique structure allows for the formation of various derivatives, which can be further modified to create a wide range of compounds with different properties and applications.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 4-NITROPHENYL-BETA-D-FUCOPYRANOSIDE is used as a starting material for the development of new drugs targeting various diseases. Its structural similarity to natural fucopyranosides makes it an attractive candidate for the design of glycomimetics, which are compounds that mimic the structure and function of natural sugars. These glycomimetics can be used to modulate biological processes, such as cell-cell interactions and signal transduction pathways, which are often dysregulated in disease states.
Used in Glycobiology Research:
4-NITROPHENYL-BETA-D-FUCOPYRANOSIDE is also utilized in glycobiology research to study the role of fucopyranosides in various biological processes. By incorporating this compound into different molecular constructs, researchers can investigate the specific interactions between fucopyranosides and their binding partners, such as proteins and other carbohydrates. This information can be valuable for understanding the molecular mechanisms underlying various biological phenomena and for the development of novel therapeutic strategies.
Used in Analytical Chemistry:
In the field of analytical chemistry, 4-NITROPHENYL-BETA-D-FUCOPYRANOSIDE can be employed as a reference compound for the development and validation of analytical methods for the detection and quantification of fucopyranosides in various samples. Its unique chemical properties, such as its UV absorbance and fluorescence characteristics, make it an ideal candidate for the development of sensitive and selective assays for the analysis of fucopyranosides in complex biological matrices.

InChI:InChI=1/C12H15NO7/c1-6-9(14)10(15)11(16)12(19-6)20-8-4-2-7(3-5-8)13(17)18/h2-6,9-12,14-16H,1H3/t6-,9+,10+,11-,12+/m1/s1

Upstream product

• 18992-37-5 4-nitrophenyl-2,3,4,6-tetra-O-acetyl-α-L-rhamnopyranoside 
• 100-02-7 4-nitro-phenol 
• 5160-09-8 2,3,4‐tri‐O‐acetyl-α-L‐rhamnopyranosyl chloride 
• 84729-97-5 p-nitrophenyl 2,3,4-tri-O-acetyl-β-D-fucopyranoside 
• 5158-64-5 2,3,4-tri-O-acetyl-D-fucopyranosyl bromide 
• 824-78-2 4-nitrophenol sodium salt 
• 51921-33-6 1,2,3,4-tetra-O-acetyl-D-fucopyranose 
• 73-34-7 D-Fucose 

Downstream Products

• 183878-99-1 1-(4-aminophenoxy)-α-L-rhamnopyranoside 
• 100-02-7 4-nitro-phenol 
• 73-34-7 D-Fucose 
• 84729-98-6 p-nitrophenyl 3,4-O-isopropylidene-β-D-fucopyranoside 
• 88043-70-3 p-nitrophenyl 2,3-O-isopropylidene-α-L-rhamnopyranoside 
• 150412-46-7 p-nitrophenyl 4-O-benzyl-α-L-rhamnopyranoside 
• 150412-47-8 p-nitrophenyl 4-O-benzyl-3-O-methyl-α-L-rhamnopyranoside 
• 150412-45-6 p-nitrophenyl 4-O-benzyl-2,3-O-isopropylidene-α-L-rhamnopyranoside 
• 1053616-06-0 4-{(2S,3R,4R,5S,6S)-5-Benzyloxy-3-[(2S,3R,4R,5S,6S)-5-((2S,3R,4S,5R,6R)-3,5-bis-benzyloxy-4-methoxy-6-methoxymethyl-tetrahydro-pyran-2-yloxy)-3,4-dimethoxy-6-methyl-tetrahydro-pyran-2-yloxy]-4-methoxy-6-methyl-tetrahydro-pyran-2-yloxy}-phenylamine 
• 150424-95-6 p-nitrophenyl 4-O-benzyl-2-O-<4-O-(2,4-di-O-benzyl-3,6-O-methyl-β-D-glucopyranosyl)-2,3-di-O-methyl-α-L-rhamnopyranosyl>-3-O-methyl-α-L-rhamnopryranoside 
• 150412-54-7 p-trifluoroacetamidophenyl 4-O-benzyl-2-O-<4-O-(2,4-di-O-benzyl-3,6-O-methyl-β-D-glucopyranosyl)-2,3-di-O-methyl-α-L-rhamnopyranosyl>-3-O-methyl-α-L-rhamnopryranoside 
• 114284-03-6 p-nitrophenyl 4-O-(3,6-di-O-acetyl-2,4-di-O-benzyl-α-D-glucopyranosyl)-2,3-O-isopropylidene-α-L-rhamnopyranoside 
• 88043-73-6 p-trifluoroacetamidophenyl 4-O-α-D-glucopyranosyl-α-L-rhamnopyranoside 
• 88043-71-4 p-nitrophenyl 2,3-O-isopropylidene-4-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-α-L-rhamnopyranoside 

Relevant articles and documents

Synthesis of aryl α-O-L-rhamnopyranoside by two-step reaction in one pot

The title compounds were conveniently synthesized by a phase transfer catalyzed approach in two steps and one pot using the rhamnopyranosyl chloride as key intermediate. The twostep one-pot procedure is more convenient and environmentally friendly, compared to the published synthetic routes. Besides, the structure-reactivity relationship and the plausible mechanism for this base-catalyzed glycosylation were discussed bymeans of the Hammett equation.

Synthesis of p-nitrophenyl 2-O-alpha- and -beta-L-fucopyranosyl-beta-D-fucopyranoside.

-