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 60761노트

반응식

HRID 60761 반응식
[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

참가 물질

4

반응물 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-dione2회

생성물 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-dione수율 74.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-bf8bfb41d82d4be8bbc07a54caa0d5f7
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09441008B2

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