116049-57-1

Basic information

• Product Name: 2-Acetamido-2,4-dideoxy-4-fluoro-D-glucopyranose
• Synonyms: 2-Acetamido-2,4-dideoxy-4-fluoro-D-glucopyranose;2-ACETAMIDO-1,3,6-TRI-O-ACETYL-2,4-DIDEOXY-4-FLUORO-D-GLUCOPYRANOSE;2-(AcetylaMino)-2,4-dideoxy-4-fluoro-D-glucopyranose 1,3,6-Triacetate
• CAS NO: 116049-57-1
• Molecular Formula: C₁₄H₂₀FNO₈
• Molecular Weight: 349.309
• Product Categories: 13C & 2H Sugars;Carbohydrates & Derivatives;Inhibitors
• Mol File: 116049-57-1.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 488.993 °C at 760 mmHg
• Flash Point: 249.534 °C
• Appearance: /
• Density: 1.298 g/cm³
• Refractive Index: 1.476
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Solubility: Methanol (Slightly, Sonicated), Water (Slightly)
• PKA: 13.20±0.70(Predicted)
• CAS DataBase Reference: 2-Acetamido-2,4-dideoxy-4-fluoro-D-glucopyranose(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Acetamido-2,4-dideoxy-4-fluoro-D-glucopyranose(116049-57-1)
• EPA Substance Registry System: 2-Acetamido-2,4-dideoxy-4-fluoro-D-glucopyranose(116049-57-1)

Safety Data

• Hazardous Substances Data: 116049-57-1(Hazardous Substances Data)

Usage

Description

2-Acetamido-2,4-dideoxy-4-fluoro-D-glucopyranose, also known as 2-Fluoro-2-deoxy-N-Acetylneuraminic Acid (FDANA), is a modified sugar molecule derived from N-Acetylglucosamine. It is a white solid with unique chemical properties that make it a potent inhibitor of P-selectin ligand activity. 2-Acetamido-2,4-dideoxy-4-fluoro-D-glucopyranose has gained significant interest in various fields due to its potential applications and therapeutic benefits.

Uses

Used in Pharmaceutical Industry:
2-Acetamido-2,4-dideoxy-4-fluoro-D-glucopyranose is used as a therapeutic agent for targeting P-selectin ligand activity. Its potent inhibition of P-selectin ligand activity makes it a promising candidate for the development of drugs aimed at treating various inflammatory and autoimmune diseases, as well as certain types of cancer.
Used in Drug Delivery Systems:
In the field of drug delivery, 2-Acetamido-2,4-dideoxy-4-fluoro-D-glucopyranose can be employed as a component in the design of targeted drug delivery systems. Its ability to inhibit P-selectin ligand activity can be utilized to enhance the specificity of drug delivery, potentially improving the efficacy and reducing the side effects of various therapeutic agents.
Used in Chemical Research:
As a modified sugar molecule, 2-Acetamido-2,4-dideoxy-4-fluoro-D-glucopyranose serves as an important compound in chemical research. It can be used as a starting material or a building block for the synthesis of various complex molecules, including novel drugs, bioactive compounds, and other specialty chemicals.
Used in Material Science:
The unique chemical properties of 2-Acetamido-2,4-dideoxy-4-fluoro-D-glucopyranose also make it a candidate for applications in material science. Its ability to interact with other molecules and form stable structures can be exploited in the development of new materials with specific properties, such as improved biocompatibility, enhanced mechanical strength, or tailored drug release profiles.

InChI:InChI=1/C14H20FNO8/c1-6(17)16-12-13(22-8(3)19)11(15)10(5-21-7(2)18)24-14(12)23-9(4)20/h10-14H,5H2,1-4H3,(H,16,17)/t10?,11-,12+,13+,14-/m1/s1

Upstream product

• 108-24-7 acetic anhydride 
• 174771-87-0 2-acetamido-2-deoxy-1,3-di-O-acetyl-6-O-(triphenylmethyl)-α-D-galactopyranose 
• 1375729-81-9 2-acetamido-2,4-dideoxy-1,3-di-O-acetyl-4-fluoro-6-O-(triphenylmethyl)-α-D-galactopyranose 
• 72-87-7 N-acetyl-D-galactosamine 
• 50605-19-1 2-acetamido-2-deoxy-1,3-di-O-acetyl-α-D-galactopyranose 
• 129728-87-6 2-acetamido-2,4-dideoxy-4-fluoro-α,β-D-glucopyranose 
• 290819-73-7 benzyl 2-acetamido-2,4-dideoxy-4-fluoro-β-D-glucopyranoside 
• 141019-70-7 Benzyl-2-acetamido-3,6-di-O-benzoyl-2-desoxy-α-D-galactopyranosid 
• 82827-77-8 Benzyl-2-acetamido-2-desoxy-3,6-di-O-dibenzoyl-α-D-glucopyranosid 
• 120596-16-9 benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-4-O-(methylsulfonyl)-α-D-glucopyranoside 
• 115973-74-5 benzyl 2-acetamido-3,6-di-O-benzyl-2,4-dideoxy-4-fluoro-α-D-glucopyranoside 
• 75869-83-9 benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-galactopyranoside 
• 129728-93-4 benzyl 2-acetamido-4-O-benzoyl-3,6-di-O-benzyl-2-deoxy-α-D-galactopyranoside 
• 14146-28-2 benzyl 2-acetamido-3-O-benzyl-2-deoxy-6-O-trityl-α-D-glucopyranoside 

Downstream Products

• 115973-78-9 benzyl 6-O-[2-acetamido-2,4-dideoxy-4-fluoro-β-D-glucopyranosyl]-2-acetamido-2-deoxy-α-D-galactopyranoside 
• 115973-77-8 benzyl 2-acetamido-6-O-(2-acetamido-3,6-di-O-acetyl-2,4-dideoxy-4-fluoro-β-D-glucopyranosyl)-3-O-acetyl-2-deoxy-α-D-galactopyranoside 

Relevant articles and documents

Synthesis and in vitro cytotoxicity of acetylated 3-fluoro, 4-fluoro and 3,4-difluoro analogs of D-glucosamine and D-galactosamine

Background: Derivatives of D-glucosamine and D-galactosamine represent an important family of the cell surface glycan components and their fluorinated analogs found use as metabolic inhibitors of complex glycan biosynthesis, or as probes for the study of protein-carbohydrate interactions. This work is focused on the synthesis of acetylated 3-deoxy-3-fluoro, 4-deoxy-4-fluoro and 3,4-dideoxy-3,4-difluoro analogs of D-glucosamine and D-galactosamine via 1,6-anhydrohexopyranose chemistry. Moreover, the cytotoxicity of the target compounds towards selected cancer cells is determined. Results: Introduction of fluorine at C-3 was achieved by the reaction of 1,6-anhydro-2-azido-2-deoxy-4-O-benzyl-β-D-glucopyranose or its 4-fluoro analog with DAST. The retention of configuration in this reaction is discussed. Fluorine at C-4 was installed by the reaction of 1,6:2,3-dianhydro-β-D-talopyranose with DAST, or by fluoridolysis of 1,6:3,4-dianhydro-2-azido-β-D-galactopyranose with KHF2. The amino group was introduced and masked as an azide in the synthesis. The 1-O-deacetylated 3-fluoro and 4-fluoro analogs of acetylated D-galactosamine inhibited proliferation of the human prostate cancer cell line PC-3 more than cisplatin and 5-fluorouracil (IC50 28 ± 3 μM and 54 ± 5 μM, respectively). Conclusion: A complete series of acetylated 3-fluoro, 4-fluoro and 3,4-difluoro analogs of D-glucosamine and D-galactosamine is now accessible by 1,6-anhydrohexopyranose chemistry. Intermediate fluorinated 1,6-anhydro-2-azido-hexopyranoses have potential as synthons in oligosaccharide assembly.

Fluorinated glucosamine analogs useful for modulating post-translational glycosylations on cells

The present invention provides compositions and methods for inhibiting cell migration, e.g., lymphocytes and inflammation. The invention also provides an improved process for preparing fluorinated N-acetylglucosamines.

Fluorinated carbohydrates as potential plasma membrane modifiers. Synthesis of 4- and 6-fluoro derivatives of 2-acetamido-2-deoxy-D-hexopyranoses.

2-Amino-2,4-dideoxy-4-fluoro- and 2-amino-2,4,6-trideoxy-4, 6-difluoro-D-galactose, and 2-amino-2,4-dideoxy-4-fluoro- and 2-amino-4-deoxy-4, 4-difluoro-D-xylo-hexose were synthesized, as potential modifiers of tumor cell-surface glyco-conjugate, from benz