Mannose Triflate

Mannose Triflate Property

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 

Solid

color 

White to Off-White

optical activity

[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|

Safety

Hazard Codes 

Xi

Safety Statements 

24/25

WGK Germany 

3

F 

10-21

HS Code 

29329990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

Mannose Triflate Chemical Properties,Usage,Production

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.

Physical properties

White to off-white powder or crystal

Chemical Properties

Colourless or nearly colourless crystals, mp 119 - 122℃; soluble in acetonitrile, DMSO, methanol, acetone, insoluble in aqueous media

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