20409-32-9

Basic information

• Product Name: 1,2,4,6-TETRA-O-ACETYL-3-DEOXY-3-FLUORO-ALPHA-D-GLUCOPYRANOSE
• Synonyms: 1,2,4,6-TETRA-O-ACETYL-3-DEOXY-3-FLUORO-ALPHA-D-GLUCOPYRANOSE
• CAS NO: 20409-32-9
• Molecular Formula: C₁₄H₁₉FO₉
• Molecular Weight: 350.293
• Mol File: 20409-32-9.mol
• Article Data: 13

Chemical Properties

• Melting Point: 109-111 °C
• Boiling Point: 408.3±45.0 °C(Predicted)
• Appearance: /
• Density: 1.30±0.1 g/cm3(Predicted)
• CAS DataBase Reference: 1,2,4,6-TETRA-O-ACETYL-3-DEOXY-3-FLUORO-ALPHA-D-GLUCOPYRANOSE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,4,6-TETRA-O-ACETYL-3-DEOXY-3-FLUORO-ALPHA-D-GLUCOPYRANOSE(20409-32-9)
• EPA Substance Registry System: 1,2,4,6-TETRA-O-ACETYL-3-DEOXY-3-FLUORO-ALPHA-D-GLUCOPYRANOSE(20409-32-9)

Safety Data

• Hazardous Substances Data: 20409-32-9(Hazardous Substances Data)

Usage

General Description

1,2,4,6-Tetra-O-acetyl-3-deoxy-3-fluoro-alpha-D-glucopyranose is a synthetic derivative of glucose that is often used as a starting material in the synthesis of complex carbohydrates and glycoconjugates. It is a modified form of glucose with four acetyl groups and a fluorine atom attached to the sugar molecule. 1,2,4,6-TETRA-O-ACETYL-3-DEOXY-3-FLUORO-ALPHA-D-GLUCOPYRANOSE is widely used in the field of carbohydrate chemistry for the production of glycolipids, glycoproteins, and glycosylated natural products. Its unique structure and properties make it a valuable tool for studying the role of carbohydrates in various biological processes and for developing new therapeutic agents.

Upstream product

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• 2595-05-3 Diacetone D-glucose 
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• 108-24-7 acetic anhydride 
• 31001-27-1 3-deoxy-3-fluoro-α-D-glucopyranose 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 127-09-3 sodium acetate 
• 7226-70-2 (3S,4S,5R,6R)-4-fluoro-6-(hydroxymethyl)tetrahydro-2H-pyran-2,3,5-triol 

Downstream Products

• 924279-85-6 1-(2,4,6-tri-O-acetyl-3-deoxy-3-fluoro-β-D-glucopyranosyl)-N⁴-benzoyl cytosine 
• 931095-50-0 [(2R,3R,4S,5R,6S)-3,5-diacetoxy-4-fluoro-6-phenylsulfanyl-tetrahydropyran-2-yl]methyl acetate 
• 1020068-54-5 9-(2,4,6-tri-O-acetyl-3-deoxy-3-fluoro-β-D-glucopyranosyl)-N⁶-benzoyl adenine 
• 7226-70-2 (3S,4S,5R,6R)-4-fluoro-6-(hydroxymethyl)tetrahydro-2H-pyran-2,3,5-triol 
• 1020068-55-6 9-(3-deoxy-3-fluoro-β-D-glucopyranosyl)-N⁶-benzoyl adenine 

Relevant articles and documents

Mechanistic Investigation of 1,2-Diol Dehydration of Paromamine Catalyzed by the Radical S-Adenosyl- l -methionine Enzyme AprD4

AprD4 is a radical S-adenosyl-l-methionine (SAM) enzyme catalyzing C3′-deoxygenation of paromamine to form 4′-oxo-lividamine. It is the only 1,2-diol dehydratase in the radical SAM enzyme superfamily that has been identified and characterized in vitro. The AprD4 catalyzed 1,2-diol dehydration is a key step in the biosynthesis of several C3′-deoxy-aminoglycosides. While the regiochemistry of the hydrogen atom abstraction catalyzed by AprD4 has been established, the mechanism of the subsequent chemical transformation remains not fully understood. To investigate the mechanism, several substrate analogues were synthesized and their fates upon incubation with AprD4 were analyzed. The results support a mechanism involving formation of a ketyl radical intermediate followed by direct elimination of the C3′-hydroxyl group rather than that of a gem-diol intermediate generated via 1,2-migration of the C3′-hydroxyl group to C4′. The stereochemistry of hydrogen atom incorporation after radical-mediated dehydration was also established.

MODULAR SYNTHESIS OF AMINOGLYCOSIDES

The present disclosure relates to novel methods for preparing antibacterial aminoglycoside compounds and the compounds used in such preparations.

3-Fluoroazetidinecarboxylic Acids and trans,trans- 3,4-Difluoroproline as Peptide Scaffolds: Inhibition of Pancreatic Cancer Cell Growth by a Fluoroazetidine Iminosugar

Reverse aldol opening renders amides of 3-hydroxyazetidinecarboxylic acids (3-OH-Aze) unstable above pH 8. Aze, found in sugar beet, is mis-incorporated for proline in peptides in humans and is associated with multiple sclerosis and teratogenesis. Aze-con