Benzyl Bromide → (2S,3R,4R,5S,6R)-3,4,5-tris(benzyloxy)-2-methyl-6-(p-tolylthio)tetrahydro-2H-pyran

HRID 1862756Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1862756
[C:1]([O:4][C@H:5]1[C@H:18]([O:19][C:20](=O)[CH3:21])[C@H:17]([O:23][C:24](=O)[CH3:25])[C@H:16]([CH3:27])[O:15][C@@H:6]1[S:7][C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=1)(=O)[CH3:2].C[O-].[Na+].CO.[H-].[Na+].[CH:35]1[CH:40]=[CH:39][C:38]([CH2:41]Br)=CC=1>CN(C=O)C.O.CCCCCC>[CH2:1]([O:4][C@H:5]1[C@H:18]([O:19][CH2:20][C:21]2[CH:5]=[CH:18][CH:17]=[CH:16][CH:27]=2)[C@H:17]([O:23][CH2:24][C:25]2[CH:41]=[CH:38][CH:39]=[CH:40][CH:35]=2)[C@H:16]([CH3:27])[O:15][C@@H:6]1[S:7][C:8]1[CH:9]=[CH:10][C:11]([CH3:14])=[CH:12][CH:13]=1)[C:2]1[CH:12]=[CH:13][CH:8]=[CH:9][CH:10]=1

Komponenten

8

Edukt 4

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 10000824p-Methylphenyl 2,3,4-Tri-O-acetyl-1-thio-beta-L-fucopyranosideHCID 23694274Sodium methanolate methanol

Produkt 1

HCID 11071610(2S,3R,4R,5S,6R)-3,4,5-tris(benzyloxy)-2-methyl-6-(p-tolylthio)tetrahydro-2H-pyranAusbeute 152,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8058HexaneLösungsmittel

Versuchsvorschrift

p-Methylphenyl 2,3,4-Tri-O-acetyl-1-thio-β-L-fucopyranoside (ibid, Brukart, M. D. et al. 1997) (2.5 g, 6.31 mmol) was treated with NaOMe-MeOH. The product was further treated with 85% NaH (463 g, 22.7 mmol) and BnBr (5.8 mL, 37.86 mmol) in DMF (25 mL). After reaction was finished, hexane (30 mL) and water (300 mL) were added into the vigorously stirred solution. The solid product was filtered, washed with water (2×5 mL) and hexane-AcOEt (15:1, 2×5 mL). The crude product was suspended in a hot (70° C.) mixture of AcOEt-Hexane (10:1), and stirred for 10 min. cooled to rt, filtered to gave pure 50 (2.6 g, 76%) as solid: [α]D22 +8° (c, 0.5, CHCl3); HRMS (M+Cs) calcd for C34H36O4SCs 672.1290, found 672.1287.

Aufarbeitung

  1. customAfter reaction
  2. filtrationThe solid product was filtered
  3. washwashed with water (2×5 mL) and hexane-AcOEt (15:1, 2×5 mL)
  4. additionThe crude product was suspended in a hot (70° C.) mixture of AcOEt-Hexane (10:1)
  5. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-8afa851ebd1049e7bbda5d0435b1d43b
Quelldatensatz
uspto-grants-2003_03
Patentnummer
US06538117B1

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