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Chemical Structure| 54094-19-8 Chemical Structure| 54094-19-8

Structure of 54094-19-8

Chemical Structure| 54094-19-8

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Product Details of [ 54094-19-8 ]

CAS No. :54094-19-8
Formula : C12H14F3O5P
M.W : 326.21
SMILES Code : FC(C1=CC(OCC(CP(OC)(OC)=O)=O)=CC=C1)(F)F
MDL No. :MFCD09054713

Safety of [ 54094-19-8 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319
Precautionary Statements:P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313

Application In Synthesis of [ 54094-19-8 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 54094-19-8 ]

[ 54094-19-8 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 31752-99-5 ]
  • [ 54094-19-8 ]
  • [ 54142-64-2 ]
YieldReaction ConditionsOperation in experiment
55% 1. Construction of the Lower Chain (Oxidation and HWE Reaction) Preparation of the [1,1?-Biphenyl]-4-carboxylic acid, (3aR,4R,5R,6aS)-hexahydro-2-oxo-4-[(1E)-3-oxo-4-[3-(trifluoromethyl)phenoxy]-1-buten-1-yl]-2H-cyclopenta[b]furan-5-yl ester /compound of formula (II)/ [0034] PPB-Corey-lactone is suspended in an inert atmosphere in 11.1 L of water-free toluene. To this suspension are added 1.4 L of diisopropylcarbodiimide and then 0.855 L of dimethyl sulfoxide in phosphoric acid. The reaction mixture is heated to 50 C. and a further 0.34 L of dimethyl sulfoxide in phosphoric acid is added in portions. After the accomplishment of the oxidation reaction, the mixture is cooled to -10 C. and while that temperature is maintained, 316 g of potassium hydroxide followed by 1.45 kg of Travoprost phosphonate in toluene solution are added. When the HWE reaction has completed, the reaction mixture is poured onto 1 M hydrochloric acid solution and the mixture is stirred. The precipitated crystals are filtered off and washed. The phases of the filtrate are separated, the organic phase is washed with 1M sodium hydrogen carbonate solution and then with diluted hydrochloric acid solution. The organic phase is evaporated and purified by chromatography on a silica gel column (eluent: toluene-ethyl acetate mixture). The main fraction is evaporated and crystallized from ethyl acetate-hexane mixture. [0036] Yield: 915 g, 55%. [0037] Melting point: 112.5-114.5 C. [0038] IR spectrum of Travoprost 1. intermediate is shown on FIG. 2. [0039] Travoprost 1. intermediate 1H, 13C and 19F NMR data: [0040] Travoprost 1. intermediate (enone-Formula (II)): [TABLE-US-00001] Coupling constant 13C/19F (Hz) Numbering (ppm) 1H (ppm) Number of 1H Multiplicity (+/- 0.2 Hz) 6 176.56 - - 7 34.46 beta: 2.96* 1 m (dd) Jgem = 17.3; J7beta,8 = 10.2 alpha: 2.55 1 d 8 42.17 3.00* 1 m (dddd) 9 83.32 5.13 1 td J8,9 = J9,10beta = 6.4; J9,10alpha = 1.3 10 37.50 beta: 2.63 1 dt Jgem = 15.2; J10beta,11 = 6.4; alpha: 2.14 1 dd J10alpha,11 = 3.6 11 78.95 5.35 1 dt J11,12 = 5.6 12 53.66 3.10 1 m (ddd) J8,12 = 5.0 13 146.19 6.99 1 dd J13,14 = 16.0; J12,13 = 8.1 14 127.24 6.44 1 d 15 194.08 - - - 16 71.12 5.17 2 s 17 158.14 - - - 18 111.16 (q) 7.22** 1 broad 3JC-18,F = 3.8; J18,20 = 1.5; J18,22 = 2.5 19 130.24 (q) - - - 2JC-19,F = 31.7 20 117.50 (q) 7.285 1 m (d) 3JC-20,F = 3.8; J20,21 = 7.8; J20,22 = 0.8; 21 130.63 7.495*** 1 m (dd) J21,22 = 8.2 22 118.75 7.20** 1 m (dd) 23 123.95 (q) - - - 1JC-23,F = 272.5 23-F -61.10 - - - (s, 3) 24 164.94 - - - 25 128.16 - - - 26, 26? 129.95 8.015 2 m J26,27 = 8.5; 27, 27? 126.87 7.81 2 m 28 144.93 - - - 29 138.77 - - - 30, 30? 127.01 7.74 2 m (dd) J30,31 = 7.4 31, 31? 129.10 7.51*** 2 m (t) J31,32 = 7.4 32 128.46 7.43 1 m (tt) J30,32~1.6
 

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