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Acetone → 4-(Hydroxymethyl)phenyl-alpha-D-galactopyranoside tetraacetate

HRID 863780
Notes
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Reaction equation

HRID 863780 reaction equation
[C:1]([O:4][C@@H:5]1[C@@H:19]([O:20][C:21](=[O:23])[CH3:22])[C@@H:18]([O:24][C:25](=[O:27])[CH3:26])[C@@H:17]([CH2:28][O:29][C:30](=[O:32])[CH3:31])[O:16][C@@H:6]1[O:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14]Br)=[CH:10][CH:9]=1)(=[O:3])[CH3:2].CC(C)=[O:35]>[N+]([O-])([O-])=O.[Ag+]>[C:1]([O:4][C@@H:5]1[C@@H:19]([O:20][C:21](=[O:23])[CH3:22])[C@@H:18]([O:24][C:25](=[O:27])[CH3:26])[C@@H:17]([CH2:28][O:29][C:30](=[O:32])[CH3:31])[O:16][C@@H:6]1[O:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][OH:35])=[CH:10][CH:9]=1)(=[O:3])[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 180AcetoneHCID 539280404-Bromomethylphenyl 2,3,4,6-tetra-O-acetyl-alpha-D-galactopyranoside

Product 1

HCID 538764924-(Hydroxymethyl)phenyl-alpha-D-galactopyranoside tetraacetateYield 56%

Reagents, catalysts & solvents 1

HCID 24470Silver NitrateCatalyst

Conditions

Temperature
25 °C

Procedure

A solution of 1.89 g of the compound 2 in 80 ml of acetone is mixed with an equal volume of a 0.1N aqueous solution of silver nitrate. The mixture is stirred at 25° C. for 2 h, the acetone is then evaporated off under reduced pressure, the remaining aqueous phase is extracted with CH2Cl2 and the extract is washed with water and then dried over anhydrous sodium sulfate, filtered and evaporated to dryness under reduced pressure. The dry residue obtained (1.52 g) is then purified by flash chromatography on a column of silica (solvent: hexane/ethyl acetate: 60/40 v/v). The product 4 (0.94 g) is obtained with a yield of 56%.

Workup

  1. customthe acetone is then evaporated off under reduced pressure
  2. extractionthe remaining aqueous phase is extracted with CH2Cl2
  3. washthe extract is washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness under reduced pressure
  7. customThe dry residue obtained (1.52 g)
  8. customis then purified by flash chromatography on a column of silica (solvent: hexane/ethyl acetate: 60/40 v/v)

Sources & evidence

ORD record
ord-bab7c0ef892342cfbe9676069e15dad2
Source dataset
uspto-grants-1996_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05561119

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes