[(2R,3R,4S,5S,6S)-3,4,6-tris(acetyloxy)-5-(trifluoromethanesulfonyloxy)oxan-2-yl]methyl acetate

• ChemBase ID: 104675
• Molecular Formular: C15H19F3O12S
• Molecular Mass: 480.3643696
• Monoisotopic Mass: 480.05493171
• SMILES: O=C(O[C@@H]1O[C@@H]([C@@H](OC(=O)C)[C@H](OC(=O)C)[C@@H]1OS(=O)(=O)C(F)(F)F)COC(=O)C)C
• Canonical SMILES: CC(=O)OC[C@H]1O[C@@H](OC(=O)C)[C@H]([C@H]([C@@H]1OC(=O)C)OC(=O)C)OS(=O)(=O)C(F)(F)F
• InChI: InChI=1S/C15H19F3O12S/c1-6(19)25-5-10-11(26-7(2)20)12(27-8(3)21)13(14(29-10)28-9(4)22)30-31(23,24)15(16,17)18/h10-14H,5H2,1-4H3/t10-,11-,12+,13+,14-/m1/s1
• InChIKey: OIBDVHSTOUGZTJ-PEBLQZBPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2R,3R,4S,5S,6S)-3,4,6-tris(acetyloxy)-5-(trifluoromethanesulfonyloxy)oxan-2-yl]methyl acetate
• IUPAC Traditional name: [(2R,3R,4S,5S,6S)-3,4,6-tris(acetyloxy)-5-(trifluoromethanesulfonyloxy)oxan-2-yl]methyl acetate
• Synonyms: β-D-Mannopyranose 1,3,4,6-tetra-O-acetate 2-O-trifluoromethanesulfonate; Mannose triflate; 1,3,4,6-TETRA-O-ACETYL-2-O-TRIFLUOROMETHANESULFONYL-β-D-MANNOPYRANOSE; TATM; 1,3,4,6-Tetra-O-acetyl-2-O-trifluoromethanesulfonyl-β-D-mannopyranose; Mannose triflate; β-D-Mannopyranose 1,3,4,6-tetra-O-acetate 2-O-trifluoromethanesulfonate; 1,3,4,6-Tetraacetate 2-(trifluoromethanesulfonate) β-D-Mannopyranose; 1,3,4,6-Tetra-O-acetyl-2-O-trifluoromethanesulfonyl-β-D-mannopyranose; 甘露糖三氟磺酸酯; 1,3,4,6-四-O-乙酰基-2-O-三氟甲磺酰-β-D-吡喃甘露糖; 甘露糖三氟甲磺酸酯; 甘露糖三氟磺酸酯

Database IDs

• CAS Number: 92051-23-5
• MDL Number: MFCD00012353
• Beilstein Number: 4341413
• PubChem SID: 162092188; 24888695; 24896669; 24884085
• PubChem CID: 11113597

CALCULATED PROPERTIES

• H Acceptors: 7
• H Donor: 0
• LogD (pH = 5.5): 0.87653726
• LogD (pH = 7.4): 0.87653726
• Log P: 0.87653726
• Molar Refractivity: 85.7323 cm^3
• Polarizability: 36.547676 Å^3
• Polar Surface Area: 157.8 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 116-120 °C; 118-122 °C
• Optical Rotation: [α]20/D -16.5±0.5°, c = 1% in chloroform; [α]20/D -16°, c = 1 in chloroform; [α]22/D -16°, c = 1 in chloroform

Safety Information

• Storage Condition: 0°C
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (TLC); 98%; 99%
• Grade: purum
• Shipped in: dry ice
• Empirical Formula (Hill Notation): C15H19F3O12S

DETAILS

Sigma Aldrich - M1568

Application
Mannose triflate is a synthetic carbohydrate precursor used the production of 2-deoxy-2-18F-β-D-glucopyranose (18FDG). 18FDG is the most commonly utilized radiotracer in positron emission tomography (PET) to study cell metabolism. FDG is naturally absorbed by cells just like glucose, but cannot be metabolized. The 18FDG radiotracer accumulates in cancer cells because of their characteristic high metabolic rate. The 18F emits low energy positrons that are detected by PET scanners.The synthesis of 18FDG requires the use of a cyclotron to produce 18F from 18O enriched water and typically utilizes an 18FDG synthesizer. A limiting factor of 18FDG use is the relatively short half-life of 18F (~100 minutes) as well as the low yield of 18FDG synthesis. The entire process from creation of 18F to synthesis of 18FDG to injection into a patient must occur within several hours. This has led to the creation of several automated 18FDG synthesizers that utilize kits to aid the process.
Other Notes
This formulation of mannose triflate has reduced trace impurities that are known to cause lower synthetic yields.

Sigma Aldrich - 310255

Packaging
20, 100 mg in glass bottle
Application
Starting material for 2-deoxy-2-18F-β-D-glucopyranose.1,2 Building block for tetrasaccharides which are precursors to O-specific polysaccharides of Shigella dysenteriae Type 1.3,4

Sigma Aldrich - 655112

Packaging
20, 100 mg in glass bottle

Sigma Aldrich - 86566

Other Notes
Carbohydrate building block for the synthesis of various derivatives of glucose modified at C-2, e.g. 2-halo-glucose1,2,3; Preparation of thioethers4

Toronto Research Chemicals - T283850

A radiolabelled pharmaceutical preparation for diagnostic aims used in positron emission tomography.

REFERENCES

• Chirakal, R., et al.: Applied Radiation Isotopes, 46, 149 (1995)
• Kuge, Y., et al.: Nuclear Med. Biol., 29, 275 ( 2002),