129785-44-0

Basic information

• Product Name: 2-acetamido-1,3,6-tri-O-acetyl-4-deoxy-4-fluoroglucopyranose
• Synonyms: 2-acetamido-1,3,6-tri-O-acetyl-4-deoxy-4-fluoroglucopyranose;[(2R,3R,4R,5S,6R)-3-Acetamido-2-Acetyloxy-6-(Acetyloxymethyl)-5-Fluorooxan-4-Yl] Acetate
• CAS NO: 129785-44-0
• Molecular Formula: C14H20 F N O8
• Molecular Weight: 349.31
• Mol File: 129785-44-0.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 489°Cat760mmHg
• Flash Point: 249.5°C
• Appearance: /
• Density: 1.29g/cm³
• Vapor Pressure: 1.04E-09mmHg at 25°C
• Refractive Index: 1.475
• CAS DataBase Reference: 2-acetamido-1,3,6-tri-O-acetyl-4-deoxy-4-fluoroglucopyranose(CAS DataBase Reference)
• NIST Chemistry Reference: 2-acetamido-1,3,6-tri-O-acetyl-4-deoxy-4-fluoroglucopyranose(129785-44-0)
• EPA Substance Registry System: 2-acetamido-1,3,6-tri-O-acetyl-4-deoxy-4-fluoroglucopyranose(129785-44-0)

Safety Data

• Hazardous Substances Data: 129785-44-0(Hazardous Substances Data)

Usage

Class

Glucopyranose (sugar)

Chemical structure

Glucose molecule with a fluorine atom substituted at the 4th carbon, acetyl groups at the 1st, 3rd, and 6th positions, and an acetamido group attached

Potential applications

Medicinal chemistry, specifically in the development of antiviral and antifungal drugs

Value as a building block

Useful for synthesizing complex organic compounds for pharmaceutical development

Potential applications in research

Glycobiology and carbohydrate-protein interactions

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

• 14146-28-2 benzyl 2-acetamido-3-O-benzyl-2-deoxy-6-O-trityl-α-D-glucopyranoside 
• 108-24-7 acetic anhydride 
• 50605-19-1 2-acetamido-2-deoxy-1,3-di-O-acetyl-α-D-galactopyranose 
• 72-87-7 N-acetyl-D-galactosamine 
• 1375729-81-9 2-acetamido-2,4-dideoxy-1,3-di-O-acetyl-4-fluoro-6-O-(triphenylmethyl)-α-D-galactopyranose 
• 174771-87-0 2-acetamido-2-deoxy-1,3-di-O-acetyl-6-O-(triphenylmethyl)-α-D-galactopyranose 
• 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 
• 55287-49-5 benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside 
• 38416-14-7 benzyl 2-acetamido-3-O-benzyl-2-deoxy-4-O-mesyl-α-D-glucopyranoside 
• 129728-87-6 2-acetamido-2,4-dideoxy-4-fluoro-α,β-D-glucopyranose 

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 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