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 60761ノート

反応式

HRID 60761 の反応式
[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

参加物

4

反応物 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 回

生成物 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-dione収率 74.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-bf8bfb41d82d4be8bbc07a54caa0d5f7
出典データセット
uspto-grants-2016_09
特許番号
US09441008B2

反応ノート

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