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

HRID 970293
Notes
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Reaction equation

HRID 970293 reaction equation
[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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028Tetrahydrofuran
Solvent

Procedure

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%).

Workup

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

Sources & evidence

ORD record
ord-7eb42925f7c4419094d9c2ebf6fd1cbe
Source dataset
uspto-grants-2007_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07312194B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes