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Lithium tri-tert-butoxyaluminohydride → 1-[(2S,4S,5R)-5-(5-amino-2,7-dioxo-6H-thiazolo[4,5-d]pyrimidin-3-yl)-4-hydroxy-tetrahydrofuran-2-yl]propyl acetate

HRID 60716
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 60716
[C:1]([O:4][CH:5]([C@@H:8]1[CH2:12][C:11](=[O:13])[C@H:10]([N:14]2[C:18]3[N:19]=[C:20]([NH2:24])[NH:21][C:22](=[O:23])[C:17]=3[S:16][C:15]2=[O:25])[O:9]1)[CH2:6][CH3:7])(=[O:3])[CH3:2].[H-].C(O[Al](OC(C)(C)C)OC(C)(C)C)(C)(C)C.[Li+]>C1COCC1>[C:1]([O:4][CH:5]([C@@H:8]1[CH2:12][C@H:11]([OH:13])[C@H:10]([N:14]2[C:18]3[N:19]=[C:20]([NH2:24])[NH:21][C:22](=[O:23])[C:17]=3[S:16][C:15]2=[O:25])[O:9]1)[CH2:6][CH3:7])(=[O:3])[CH3:2]
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Komponenten

4

Edukt 2

HCID 16710494Lithium tri-tert-butoxyaluminohydrideHCID 1371087081-[(2S,5R)-5-(5-amino-2,7-dioxo-6H-thiazolo[4,5-d]pyrimidin-3-yl)-4-oxo-tetrahydrofuran-2-yl]propyl acetate2×

Produkt 1

HCID 1371087351-[(2S,4S,5R)-5-(5-amino-2,7-dioxo-6H-thiazolo[4,5-d]pyrimidin-3-yl)-4-hydroxy-tetrahydrofuran-2-yl]propyl acetateAusbeute 62,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel

Versuchsvorschrift

To a stirred solution of 1-[(2S,5R)-5-(5-amino-2,7-dioxo-6H-thiazolo[4,5-d]pyrimidin-3-yl)-4-oxo-tetrahydrofuran-2-yl]propyl acetate (compound 22b, 2.8 g, 7.6 mmol) in THF (50 mL) was added lithium tri-tert-butoxyaluminum hydride (1M in THF, 15 mL, 15 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 1.76 g crude product of 1-[(2S,4S,5R)-5-(5-amino-2,7-dioxo-6H-thiazolo[4,5-d]pyrimidin-3-yl)-4-hydroxy-tetrahydrofuran-2-yl]propyl acetate (compound 22c). MS obsd. (ESI−) [(M−H)+]: 369. (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-d3ab1020fdd64085afff1a70227ea477
Quelldatensatz
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09441008B2

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