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(1S,2S,3S,4R,5S)-2,3,4-tribenzyloxy-5-[4-chloro-3-[(2,3-difluoro-4-methoxy-phenyl)methyl]phenyl]-6,8-dioxabicyclo[3.2.1]octane-1-carbaldehyde → HCID 131736389, Verbindung

HRID 1055576
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Reaktionsgleichung

Reaktionsgleichung von HRID 1055576
[CH2:1]([O:8][C@H:9]1[C@H:15]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C@@H:14]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C@:13]2([C:33]3[CH:38]=[CH:37][C:36]([Cl:39])=[C:35]([CH2:40][C:41]4[CH:46]=[CH:45][C:44]([O:47][CH3:48])=[C:43]([F:49])[C:42]=4[F:50])[CH:34]=3)[O:32][C@@:10]1([CH:51]=[O:52])[CH2:11][O:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:53][Mg]Br>O1CCCC1>[CH2:1]([O:8][C@H:9]1[C@H:15]([O:16][CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C@@H:14]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C@:13]2([C:33]3[CH:38]=[CH:37][C:36]([Cl:39])=[C:35]([CH2:40][C:41]4[CH:46]=[CH:45][C:44]([O:47][CH3:48])=[C:43]([F:49])[C:42]=4[F:50])[CH:34]=3)[O:32][C@@:10]1([CH:51]([OH:52])[CH3:53])[CH2:11][O:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
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Komponenten

4

Edukt 2

HCID 122610446(1S,2S,3S,4R,5S)-2,3,4-tribenzyloxy-5-[4-chloro-3-[(2,3-difluoro-4-methoxy-phenyl)methyl]phenyl]-6,8-dioxabicyclo[3.2.1]octane-1-carbaldehydeHCID 178418573HCID 178418573, Verbindung

Produkt 1

HCID 131736389HCID 131736389, VerbindungAusbeute 27,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of (1S,2S,3S,4R,5S)-2,3,4-tribenzyloxy-5-[4-chloro-3-[(2,3-difluoro-4-methoxy-phenyl)methyl]phenyl]-6,8-dioxa bicyclo[3.2.1]octane-1-carbaldehyde 21p (0.50 g, 0.69 mmol) in dry tetrahydrofuran (10 mL) was added dropwise methylmagnesium bromide (0.46 mL, 1.38 mmol, 3M in ethyl ether) under N2 at 0° C. The mixture was stirred at room temperature for 2 hours and quenched with water (10 mL). The resulting mixture was extracted with ethyl acetate (10 mL×3). The combined organic layers were washed with saturated aqueous sodium chloride (15 mL), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo and the residue was purified by silica gel chromatography eluted with PE/EtOAc(v/v)=15/1 to give the title compound 21q as a white solid (0.14 g, 19%). The compound was characterized by the following spectroscopic data: 1H NMR (400 MHz, CDCl3) δ(ppm): 7.41 (s, 3H), 7.31 (m, 9H), 7.21 (m, 4H), 6.98-6.86 (m, 2H), 6.68 (m, 1H), 6.53 (m, 1H), 4.96 (m, 2H), 4.80 (m, 2H), 4.34-4.24 (m, 2H), 4.16-4.05 (m, 4H), 3.98 (m, 2H), 3.85 (s, 3H), 3.82 (dd, 1H), 3.70 (m, 1H), 1.27 (d, 3H).

Aufarbeitung

  1. customquenched with water (10 mL)
  2. extractionThe resulting mixture was extracted with ethyl acetate (10 mL×3)
  3. washThe combined organic layers were washed with saturated aqueous sodium chloride (15 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo
  7. customthe residue was purified by silica gel chromatography
  8. washeluted with PE/EtOAc(v/v)=15/1

Quellen und Nachweise

ORD-Eintrag
ord-79964e416a154b1794d10e8b8592bd32
Quelldatensatz
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09394329B2

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