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Methanol → (2R,3S,4S,5R,6R)-2-(Acetoxymethyl)-6-aminotetrahydro-2H-pyran-3,4,5-triyl triacetate

HRID 970293
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HRID 970293 반응식
[C:1]([O:4][C@@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@@H:8]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[O:7][C@H:6]1[N:24]=[N+]=[N-])(=[O:3])[CH3:2].CO>[Pd].C1COCC1>[C:1]([O:4][C@@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@@H:8]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[O:7][C@H:6]1[NH2:24])(=[O:3])[CH3:2]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 2

HCID 887MethanolHCID 2781041beta-D-Galactopyranosyl azide, 2,3,4,6-tetraacetate

생성물 1

HCID 11393874(2R,3S,4S,5R,6R)-2-(Acetoxymethyl)-6-aminotetrahydro-2H-pyran-3,4,5-triyl triacetate수율 86%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 8028Tetrahydrofuran용매

실험 절차

Palladium catalyst (10% on carbon, 20.0 mg) was added in one portion to a solution of 2,3,4,6-tetra-O-acetyl-β-D-galacto-pyranosyl azide (6)(500 mg, 1.34 mmol) in abs. methanol (5 ml) under a hydrogen atmosphere. A small amount of abs. THF was added to dissolve the sugar. The solution was allowed to stir for 12 hours. The catalyst was subsequently filtered off, and the solvent evaporated. Purification by column chromatography gave (11) (400 mg, 86%).

후처리

  1. filtrationThe catalyst was subsequently filtered off
  2. customthe solvent evaporated
  3. customPurification by column chromatography

출처 및 근거

ORD 기록
ord-7eb42925f7c4419094d9c2ebf6fd1cbe
출처 데이터셋
uspto-grants-2007_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07312194B2

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