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[ CAS No. 805245-41-4 ]

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2D
Chemical Structure| 805245-41-4
Chemical Structure| 805245-41-4
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Product Details of [ 805245-41-4 ]

CAS No. :805245-41-4MDL No. :MFCD25977137
Formula : C44H45FO4Si Boiling Point : 681.5°C at 760 mmHg
Linear Structure Formula :-InChI Key :N/A
M.W :684.91Pubchem ID :86268842
Synonyms :

Computed Properties of [ 805245-41-4 ]

TPSA : - H-Bond Acceptor Count : -
XLogP3 : - H-Bond Donor Count : -
SP3 : - Rotatable Bond Count : -

Safety of [ 805245-41-4 ]

Signal Word:WarningClass:N/A
Precautionary Statements:P261-P305+P351+P338UN#:N/A
Hazard Statements:H302-H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 805245-41-4 ]

  • Upstream synthesis route of [ 805245-41-4 ]
  • Downstream synthetic route of [ 805245-41-4 ]

[ 805245-41-4 ] Synthesis Path-Upstream   1~12

  • 1
  • [ 805245-40-3 ]
  • [ 805245-41-4 ]
YieldReaction ConditionsOperation in experiment
73% With n-butyllithium; N-fluorobis(benzenesulfon)imide In tetrahydrofuran; hexane at -78℃; for 1 h; (3R,4R,6aR)-tert-Butyl-(5-fluoro-2,2-dimethyl-6-trityloxymethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-yloxy)-diphenyl-silane (11)
To a stirred solution of 10 (11.66 g, 14.71 mmol) and N-fluorobenzenesulfonimide (5.566 g, 17.65 mmol) in dry tetrahydrofuran (100 ml) was slowly added n-butyllithum (27.6 ml, 44.13 mmol, 1.6 M solution in hexanes) at -78° C. under nitrogen atmosphere and the reaction mixture was stirred at the same temperature for 1 hour.
The mixture was quenched with saturated ammonium chloride solution and extracted with ethyl acetate.
The organic layer was dried over anhydrous magnesium sulfate, and evaporated.
The residue was purified by flash silica gel column chromatography (hexane:ethyl acetate=6:1) to afford 11 (7.35 g, 73percent) as a white solid; 1H NMR (400 MHz, CDCl3) δ 7.81-7.17 (m, 25H), 4.94 (t, J=7.2 Hz, 1H), 4.35 (m, 1H), 4.25 (m, 1H), 3.89 (t, J=12.0 Hz, 1H), 3.77 (t, J=12.0 Hz, 1H), 1.42 (s, 3H), 1.38 (s, 3H), 1.08 (s, 9H).
Reference: [1] Patent: US2005/222185, 2005, A1, . Location in patent: Page/Page column 7
[2] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 22, p. 5641 - 5644
[3] Nucleosides, Nucleotides and Nucleic Acids, 2005, vol. 24, # 5-7, p. 707 - 708
[4] Patent: WO2014/145807, 2014, A1, . Location in patent: Page/Page column 9; 26; 27
[5] Patent: WO2014/145807, 2014, A1,
  • 2
  • [ 805245-40-3 ]
  • [ 805245-41-4 ]
YieldReaction ConditionsOperation in experiment
45% With n-butyllithium; N-fluorobis(benzenesulfon)imide In tetrahydrofuran; hexane; n-heptane; tert-butyl methyl ether at -78℃; for 1.5 h; Inert atmosphere n-Butyllithium (11 mL, 17.6 mmol, 1.6M solution in hexanes)was added dropwise to a cooled (78 °C) solution of 7 [9] (5.58 g,7.04 mmol) and N-fluorobenzenesulfonimide (3.33 g, 10.56 mmol)in anhydrous THF/tert-butyl methyl ether/n-heptane (3:1:1.5,90 mL total, 0.08 M) over a period of 1 h under N2. After stirring atthe same temperature for 30 min, the reaction mixture wasquenched with saturated aqueous NH4Cl (100 mL) and was dilutedwith EtOAc (100 mL). Then the layers were separated and theaqueous layer was extracted with EtOAc (2 x 50 mL). The combinedorganic layers were washed successively with H2O and brine, driedover anhydrous MgSO4, filtered, and evaporated. Finally, the residuewas purified by medium pressure liquid chromatography(silica gel, hexanes/EtOAc = 25/1) to give vinyl fluoride 8a (2.17 g,45percent), 8b (1.03 g, 22percent) and 8c (0.84 g, 18percent).8a: [α]D25-8.42 (c 0.19, MeOH); 1H NMR (400 MHz, CDCl3)δ 7.80 (d, J 6.6 Hz, 2 H), 7.72 (d, J 6.6 Hz, 2 H), 7.35-7.44 (m,13 H), 7.16-7.27 (m, 8 H), 4.93 (t, J = 6.6 Hz, 1 H), 4.34 (s, 1 H),3.22-3.25 (m, 1 H), 3.89 (d, J = 11.8 Hz, 1 H), 3.77 (d, J = 12.3 Hz,1 H), 1.44 (s, 3 H), 1.38 (s, 3 H), 1.07 (s, 9 H); 13C NMR (100 MHz,CDCl3) δ 157.3 (d, J = 288.0 Hz), 143.8, 136.0 (d, J = 23.1 Hz), 133.5 (d,J = 21.2 Hz), 129.7 (d, J = 4.9 Hz), 127.7, 127.5 (d, J = 9.2 Hz), 127.0,115.6 (d, J = 4.2 Hz), 111.8, 87.0, 78.6 (d, J = 8.8 Hz), 75.3 (d,J = 7.2 Hz), 71.0 (d, J = 18.9 Hz), 56.3, 29.5 (d, J = 29.8), 27.9, 27.2,26.7, 19.4; 19F NMR (376 MHz, CDCl3) δ -128.2; MS (ESI+) found707.2968 [calcd for C44H45FNaO4Si (M + Na)+ 707.2969].
Reference: [1] European Journal of Medicinal Chemistry, 2018, vol. 155, p. 406 - 417
  • 3
  • [ 805245-38-9 ]
  • [ 805245-41-4 ]
Reference: [1] Nucleosides, Nucleotides and Nucleic Acids, 2005, vol. 24, # 5-7, p. 707 - 708
[2] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 22, p. 5641 - 5644
[3] Patent: WO2014/145807, 2014, A1,
[4] Patent: WO2014/145807, 2014, A1,
[5] Patent: US2005/222185, 2005, A1,
  • 4
  • [ 805245-39-0 ]
  • [ 805245-41-4 ]
Reference: [1] Nucleosides, Nucleotides and Nucleic Acids, 2005, vol. 24, # 5-7, p. 707 - 708
[2] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 22, p. 5641 - 5644
[3] Patent: WO2014/145807, 2014, A1,
[4] Patent: WO2014/145807, 2014, A1,
[5] Patent: US2005/222185, 2005, A1,
  • 5
  • [ 88559-56-2 ]
  • [ 805245-41-4 ]
Reference: [1] Nucleosides, Nucleotides and Nucleic Acids, 2005, vol. 24, # 5-7, p. 707 - 708
[2] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 22, p. 5641 - 5644
[3] Patent: US2005/222185, 2005, A1,
  • 6
  • [ 67814-68-0 ]
  • [ 805245-41-4 ]
Reference: [1] Patent: US2005/222185, 2005, A1,
  • 7
  • [ 54503-64-9 ]
  • [ 805245-41-4 ]
Reference: [1] Patent: US2005/222185, 2005, A1,
  • 8
  • [ 95666-80-1 ]
  • [ 805245-41-4 ]
Reference: [1] Patent: US2005/222185, 2005, A1,
  • 9
  • [ 681853-96-3 ]
  • [ 805245-41-4 ]
Reference: [1] Patent: US2005/222185, 2005, A1,
  • 10
  • [ 865838-13-7 ]
  • [ 805245-41-4 ]
Reference: [1] Patent: US2005/222185, 2005, A1,
  • 11
  • [ 865838-12-6 ]
  • [ 805245-41-4 ]
Reference: [1] Patent: US2005/222185, 2005, A1,
  • 12
  • [ 77-76-9 ]
  • [ 805245-41-4 ]
Reference: [1] Patent: WO2014/145807, 2014, A1,
[2] Patent: WO2014/145807, 2014, A1,
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