Lithium tri-tert-butoxyaluminohydride → 5-amino-3-[(2R,3S,5S)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-hydroxy-tetrahydrofuran-2-yl]-6H-thiazolo[4,5-d]pyrimidine-2,7-dione

HRID 60761Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 60761
[NH2:1][C:2]1[NH:3][C:4](=[O:27])[C:5]2[S:10][C:9](=[O:11])[N:8]([C@H:12]3[C:16](=[O:17])[CH2:15][C@@H:14]([CH2:18][O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])[O:13]3)[C:6]=2[N:7]=1.[H-].C(O[Al](OC(C)(C)C)OC(C)(C)C)(C)(C)C.[Li+]>C1COCC1>[NH2:1][C:2]1[NH:3][C:4](=[O:27])[C:5]2[S:10][C:9](=[O:11])[N:8]([C@H:12]3[C@@H:16]([OH:17])[CH2:15][C@@H:14]([CH2:18][O:19][Si:20]([C:23]([CH3:25])([CH3:24])[CH3:26])([CH3:22])[CH3:21])[O:13]3)[C:6]=2[N:7]=1

Komponenten

4

Edukt 2

HCID 16710494Lithium tri-tert-butoxyaluminohydrideHCID 1371902205-amino-3-[(2R,5S)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-oxo-tetrahydrofuran-2-yl]-6H-thiazolo[4,5-d]pyrimidine-2,7-dione2×

Produkt 1

HCID 1371902215-amino-3-[(2R,3S,5S)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-hydroxy-tetrahydrofuran-2-yl]-6H-thiazolo[4,5-d]pyrimidine-2,7-dioneAusbeute 74,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of 5-amino-3-[(2R,5S)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-oxo-tetrahydrofuran-2-yl]-6H-thiazolo[4,5-d]pyrimidine-2,7-dione (compound 38e, 1.0 g, 2.43 mmol) in THF (5 mL) was added lithium tri-tert-butoxyaluminum hydride solution (1M in THF, 2.7 mL, 2.7 mmol). After being stirred at room temperature for 2 hours, the resulting solution was quenched by saturated NH4Cl solution and filtered. The filtrate was concentrated in vacuo and the residue was purified by column chromatography on silica gel (eluting with 1:10 methanol in DCM) to afford 750 mg crude product of 5-amino-3-[(2R,3S,5S)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-hydroxy-tetrahydrofuran-2-yl]-6H-thiazolo[4,5-d]pyrimidine-2,7-dione (compound 38f). (Refer to Tetrahedron 1984, 40, 125-135).

Aufarbeitung

  1. customthe resulting solution was quenched by saturated NH4Cl solution
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe residue was purified by column chromatography on silica gel (eluting with 1:10 methanol in DCM)

Quellen und Nachweise

ORD-Eintrag
ord-bf8bfb41d82d4be8bbc07a54caa0d5f7
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09441008B2

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