49560-82-9

Basic information

• Product Name: 1,2,3,4,6-Pentakis-O-(trifluoroacetyl)hexopyranose
• Synonyms: 1,2,3,4,6-Pentakis-O-(trifluoroacetyl)hexopyranose;α-D-Galactopyranose pentakis(trifluoroacetate)
• CAS NO: 49560-82-9
• Molecular Formula: C16H7F15O11
• Molecular Weight: 660.196228
• Mol File: 49560-82-9.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1,2,3,4,6-Pentakis-O-(trifluoroacetyl)hexopyranose(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,3,4,6-Pentakis-O-(trifluoroacetyl)hexopyranose(49560-82-9)
• EPA Substance Registry System: 1,2,3,4,6-Pentakis-O-(trifluoroacetyl)hexopyranose(49560-82-9)

Safety Data

• Hazardous Substances Data: 49560-82-9(Hazardous Substances Data)

Usage

Type of compound

Derivative of hexopyranose, a six-carbon sugar molecule

Fluorination

Highly fluorinated

Substitution

Each hydroxyl group is substituted with a trifluoroacetyl (-C2F3O) group

Stability

Increased stability due to trifluoroacetyl substitution

Lipophilicity

Increased lipophilicity due to trifluoroacetyl substitution

Metabolic resistance

Enhanced metabolic resistance due to trifluoroacetyl substitution

Primary use

Chemical intermediate in the synthesis of other fluorinated compounds

Potential applications

Investigated for use in medicinal chemistry

Specific fields

Development of pharmaceuticals and agrochemicals

Upstream product

• 10257-28-0 D-Galactose 
• 685-27-8 2,2,2-trifluoro-N-methyl-N-(2,2,2-trifluoroacetyl)acetamide 
• 388-35-2 Trifluoro-acetic acid 2,3,5-tris-(2,2,2-trifluoro-acetoxy)-6-(2,2,2-trifluoro-acetoxymethyl)-tetrahydro-pyran-4-yl ester 

Downstream Products

• 388-35-2 1,2,3,4,6-penta-O-trifluoroacetyl-α-D-glucopyranose 
• 388-35-2 Trifluoro-acetic acid (2S,3S,4R,5S,6S)-2,3,5-tris-(2,2,2-trifluoro-acetoxy)-6-(2,2,2-trifluoro-acetoxymethyl)-tetrahydro-pyran-4-yl ester 
• 388-35-2 Trifluoro-acetic acid (2R,3S,4R,5S,6S)-2,3,5-tris-(2,2,2-trifluoro-acetoxy)-6-(2,2,2-trifluoro-acetoxymethyl)-tetrahydro-pyran-4-yl ester 
• 438-98-2 1,2,3,4,5-penta-O-trifluoroacetyl-β-D-glucopyranose 

Relevant articles and documents

1H-nuclear magnetic resonance spectroscopy of reducing-residue anomeric protons of pertrifluoroacetylated carbohydrates.

Eight monosaccharides (L-arabinoside, L-fucose, D-galactose, D-glucose, D-lyxose, D-mannose, L-rhamnose, and D-xylose), eight disaccharides (cellobiose, gentiobiose, isomaltose, lactose, maltose, nigerose, sophorose, and xylobiose), and three trisaccharides (isomaltotriose, maltotriose, and xylotriose) were derivatized with N-methylbis-(trifluoroacetamide) in pyridine solution to form trifluoroacetylated derivatives. These were analyzed by 1H-n.m.r. spectroscopy to determine the characteristics of the spectra and distributions of the reaction products. Peaks corresponding to reducing-residue anomeric protons were located significantly downfield of all others, and were in general 0.4 p.p.m. or more downfield of equivalent signals from the same carbohydrates when they were free or derivatized with other groups. Neither the location of anomeric proton peaks relative to each other nor the degree of spin-spin coupling between H-1 and H-2 varied greatly with type of derivatization. Spin-spin coupling, however, decreased for some beta-pyranose forms of xylobiose and the three trisaccharides. In all examples except some where H-2 was oriented equatorially to a pyranose ring, the proportion of the alpha-pyranose was either enhanced or not changed in concentration by trifluoroacetylation.