Imidazole → (2R,3S,5R)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]tetrahydrofuran-2,3,4-triol

HRID 60718

Reaktionsgleichung

Reaktionsgleichung von HRID 60718
[O:1]=[CH:2][C@H:3]([C@@H:5]([C@@H:7]([CH2:9][OH:10])[OH:8])[OH:6])[OH:4].N1C=CN=C1.[C:16]([Si:20](Cl)([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([CH3:19])([CH3:18])[CH3:17]>CN(C=O)C.CCOC(C)=O>[Si:20]([O:1][CH2:2][C@H:3]1[O:4][C@@H:9]([OH:10])[C@@H:7]([OH:8])[CH:5]1[OH:6])([C:16]([CH3:19])([CH3:18])[CH3:17])([C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Komponenten

6

Edukt 3

HCID 795ImidazoleHCID 66308D-ArabinoseHCID 94078tert-Butyldiphenylchlorosilane

Produkt 1

HCID 131737102(2R,3S,5R)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]tetrahydrofuran-2,3,4-triolAusbeute 25,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a stirred solution of D-arabinose (50 g, 0.33 mol) in DMF (500 mL) was added imidazole (45 g, 0.66 mol) and tert-butylchlorodiphenylsilane (109 g, 0.4 mol). After being stirred at room temperature for 2 hours, the resulting solution was diluted with EtOAc (2000 mL), washed with water, brine and dried over Na2SO4. The organic layer was concentrated in vacuo and the residue was purified by column chromatography on silica gel (eluting with 1:11 EtOAc in petroleum ether) to afford 33 g of (2R,3S,5R)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]tetrahydrofuran-2,3,4-triol (compound 25a).

Aufarbeitung

  1. washwashed with water, brine
  2. dry with materialdried over Na2SO4
  3. concentrationThe organic layer was concentrated in vacuo
  4. customthe residue was purified by column chromatography on silica gel (eluting with 1:11 EtOAc in petroleum ether)

Quellen und Nachweise

ORD-Eintrag
ord-8f78f4534f214d0aa8ff1322a63c61e7
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09441008B2

Verknüpfte Notizen

Wird geladen…