| Identification | Back Directory | [Name]
TATM | [CAS]
92051-23-5 | [Synonyms]
TATM
TATM USP/EP/BP
MANNOSE TRIFLATE
MANNOSE TRIFLATE F
beta-D-Mannopyranose
Mannose triflate≥ 99%(GC)
1,3,4,6-Tetra-O-acetyl-2-O-
Mannose Triflate, ultra pure
Mannose Triflate PLUS, ultra pure
Tetra-O-acetyl-mannose triflate CRS
TETRA-O-ACETYL-2-O-TRIFLUOROMETHANE- &
BETA-D-MANNOPYRANOSE 1,3,4,6-TETRA-O-AC&
1,3,4,6-Tetra-O-acetyl-2-O-trifluoroMethane
tetra-O-acetyl-2-O-trifluoromethane-sulfonyl-beta
1,3,4,6-Tetraacetate 2-(trifluoroMethanesulfonate)
BETA-D-MANNOPYRANOSE 1,3,4,6-TETRAACETATE 2-TRIFLATE
1,3,4,6-TETRA-O-ACETYL-2-O-TRIFLUORO-*METHANESULFONY
1,3,4,6-Tetra-O-acetyl-2-O-trifluoromethanesulfonyl-
Mannose Triflate, ultra pure packing for GE Microlab
1,3,4,6-tetra-O-acetyl-2-O-triflat-beta-D-mannopyranose
tetraacetyltrifluoromethanesulfonyl-beta-D-mannopyranose
Mannose Triflate, ultra pure packing for GE TRACERlab MXFDG
TATM, 1,3,4,6-Tetra-O-acetyl-2-O-triflyl-beta-D-mannopyranose
Mannose triflate C15H19F3O12S high quality Cas number：92051-23-5
1,3,4,6-Tetraacetate 2-(trifluoromethanesulfonate) -D-Mannopyranose
1,3,4,6-Tetra-O-acetyl-2-O-trifluoromethylsulfonyl-β-D-mannopyranose
b-D-Mannopyranose,1,3,4,6-tetraacetate 2-(trifluoroMethanesulfonate)
1,3,4,6-TETRA-O-ACETYL-2-O-TRIFLUOROMETHYLSULFONYL-B-D-MANNOPYRANOSE
1,3,4,6-TETRA-O-ACETYL-2-O-TRIFLUOROMETHYLSULPHONYL-B-D-MANNOPYRANOSE
1,3,4,6-Tetra-O-acetyl-2-O-trifluoromethanesulfonyl-b-D-mannopyranose
β-D-Maopyranose 1,3,4,6-tetra-O-acetate 2-O-trifluoromethanesulfonate
β-D-Mannopyranose, 1,3,4,6-tetraacetate 2-(trifluoromethanesulfonate)
1,3,4,6-Tetra-O-acetyl-2-O-trifluoromethanesulfonyl-β-D-mannopyranose
β-D-Mannopyranose1,3,4,6-tetra-O-acetate2-O-trifluoromethanesulfonate
1,3,4,6-Tetra-O-acetyl-2-O-trifluoromethanesulfonyl-β-D-mannopyranose
β-D-Mannopyranose 1,3,4,6-tetra-O-acetate 2-O-trifluoromethanesulfonate
1,3,4,6-TETRA-O-ACETYL-2-O-TRIFLUOROMETHANSULFONYL-BETA-D-MANNOPYRANOSE
1,3,4,6-tetra-O-acetate 2-O-trifluoromethanesulfonate-β-D-Mannopyranose
1,3,4,6-Tetra-O-Acetyl-2-O-(trifluoromethanesulfonyl)-a-D-mannopyranose
1,3,4,6-TETRA-O-ACETYL-2-O-TRIFLUORO-METHANESULFONYL-BETA-D-MANNOPYRANOSE
BETA-D-MANNOPYRANOSE, 1,3,4,6-TETRAACETATE 2-(TRIFLUOROMETHANE-SULFONATE)
BETA-D-MANNOPYRANOSE 1,3,4,6-TETRA-O-ACETATE 2-O-TRIFLUOROMETHANESULFONATE
1,3,4,6-TETRA-O-ACETYL-2-O-TRIFLUOROMETHYLSULFONYL-B-D-MANNOPYRANOSE, TATM
1-O,3-O,4-O,6-O-Tetraacetyl-2-O-trifluoromethanesulfonyl-β-D-mannopyranose
1-O,3-O,4-O,6-O-Tetraacetyl-2-O-(trifluoromethylsulfonyl)-β-D-mannopyranose
1,3,4,6-Tetra-O-acetyl-2-O-[(trifluoromethyl)sulphonyl]-beta-D-mannopyranose
β-D-Mannopyranose 1,3,4,6-tetra-O-acetate 2-O-trifluoromethanesulfonate(TATM)
TATM,1,3,4,6-Tetra-O-acetyl-2-O-trifluoromethanesulfonyl-beta-D-mannopyranose
beta-D-Mannopyranose 1,3,4,6-tetra-O-acetate 2-O-trifluoroMethanesulfonate 98%
acetic acid [3,4,6-triacetyloxy-5-(trifluoromethylsulfonyloxy)-2-oxanyl]methyl ester
1,3,4,6-TETRA-O-ACETYL-2-O-TRIFLUOROMETHYLSULFONYL-B-D-MANNOPYRANOSE(MANNOSE TRIFLATE)
β-D-Mannopyranose 1,3,4,6-tetra-O-acetate 2-O-trifluoromethanesulfonate Mannose triflate
[(2R,3R,4S,5S,6S)-3,4,6-triacetyloxy-5-(trifluoromethylsulfonyloxy)oxan-2-yl]methyl acetate
Mannose triflate, TATM, 1,3,4,6-Tetra-O-acetyl-2-O-trifluoromethanesulfonyl-β-D-mannopyranose
β-D-Mannopyranose 1,3,4,6-tetra-O-acetate 2-O-trifluoromethanesulfonate,1,3,4,6-Tetra-O-acetyl-2-O-trifluoromethanesulfonyl-β-D-mannopyranose, Mannose triflate, TATM | [EINECS(EC#)]
200-001-8 | [Molecular Formula]
C15H19F3O12S | [MDL Number]
MFCD00012353 | [MOL File]
92051-23-5.mol | [Molecular Weight]
480.36 |
| Chemical Properties | Back Directory | [Melting point ]
118-122 °C
| [alpha ]
[α]D20 -14～-17゜(c=1,CHCl3) | [Boiling point ]
481.6±45.0 °C(Predicted) | [density ]
1.50±0.1 g/cm3(Predicted) | [refractive index ]
-16 ° (C=1, CHCl3) | [storage temp. ]
−20°C
| [solubility ]
Chloroform (Slightly), Ethyl Acetate (Slightly) | [form ]
neat | [color ]
White to Off-White | [Optical Rotation]
[α]22/D -16°, c = 1 in chloroform | [BRN ]
4341413 | [InChI]
InChI=1/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-/s3 | [InChIKey]
OIBDVHSTOUGZTJ-UBBZJQTNNA-N | [SMILES]
[C@H]1(OC(=O)C)[C@H](OC(=O)C)[C@H](O[C@@H](OC(=O)C)[C@H]1OS(=O)(=O)C(F)(F)F)COC(=O)C |&1:0,5,10,12,17,r| |
| Hazard Information | Back Directory | [Description]
Mannose triflate is a glucose analog. Mannose triflate is a well-known precursor for 18F-FDG synthesis for PET applications. 18F-FDG is an imaging technique for cancer.
| [Chemical Properties]
White to off-white powder or crystal | [Physical properties]
White to off-white powder or crystal | [Uses]
1,3,4,6-Tetra-O-acetyl-2-O-trifluoromethanesulfonyl-beta-D-mannopyranose is a radiolabelled pharmaceutical preparation for diagnostic aims used in positron emission tomography.
| [Preparation]
The tetraacetyl mannose (1.8 g, 5 mmol) was dissolved in anhydrous CH2Cl2(14 mL) containing dry pyridine (0.9 mL, 11 mmol). This solution was cooled to -15°C, and trifluoromethanesulfonic anhydride (triflic anhydride) (0.9 mL, 5.2 mmol) was added dropwise over 25 min under a nitrogen atmosphere with vigorous stirring. The mixture was then allowed to reach room temperature overnight. The reaction mixture was successively washed with ice-cold saturated aqueous NaHCO3(50 mL) and water (50 mL). The organic layer was dried over anhydrous Na2SO4, filtered, and concentrated on a rotary evaporator.2-Tf-O-AcManwas isolated by column chromatography on silica with hexane :EtOAc=1: 1 as the eluant as white solid Mannose triflate(1.4 g, 56percent).
| [Synthesis]
General procedure for the synthesis of mannose trifluorosulfonate from trifluoromethanesulfonic anhydride and (2S,3S,4R,5R,6R)-6-(acetyloxymethyl)-3-hydroxytetrahydro-2H-pyran-2,4,5-triyltriacetate: tetraacetylmannose (5, 1.8 g, 5 mmol) was dissolved in anhydrous pyridine (0.9 mL, 11 mmol) containing anhydrous dichloromethane (14 mL). The solution was cooled to -15°C and trifluoromethanesulfonic anhydride (0.9 mL, 5.2 mmol) was added slowly and dropwise over 25 min under vigorous stirring and nitrogen protection. Subsequently, the reaction mixture was slowly warmed to room temperature and stirred overnight. Upon completion of the reaction, the reaction mixture was washed sequentially with ice-cold saturated aqueous sodium bicarbonate solution (50 mL) and deionized water (50 mL). The organic layer was dried with anhydrous sodium sulfate, filtered, and concentrated on a rotary evaporator. The product was purified by silica gel column chromatography using hexane:ethyl acetate (1:1, v/v) as eluent to afford mannose trifluorosulfonate (1.4 g, 56% yield) in white solid form. Thin layer chromatography (TLC) showed an Rf value of 0.5 (unfolding agent: hexane: ethyl acetate = 1:1). | [References]
[1] Tetrahedron, 1992, vol. 48, # 47, p. 10249 - 10264
[2] Journal of the American Chemical Society, 2010, vol. 132, # 21, p. 7405 - 7417
[3] Carbohydrate Research, 1991, vol. 210, p. 333 - 337
[4] Organic and Biomolecular Chemistry, 2009, vol. 7, # 3, p. 564 - 575
[5] Carbohydrate Research, 1984, vol. 128, p. 291 - 296 |
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