HCID 86600678, compound → HCID 86600680, compound

HRID 2106422Notes

Reaction equation

HRID 2106422 reaction equation
C([O:8][C@@H:9]1[C@@H:15]([O:16]CC2C=CC=CC=2)[C@H:14]([O:24]CC2C=CC=CC=2)[C@@H:13]([CH2:32][O:33]CC2C=CC=CC=2)[O:12][C@@:10]1([C:41]1[CH:46]=[CH:45][C:44]([CH3:47])=[C:43]([CH2:48][C:49]2[CH:54]=[CH:53][C:52]([C:55]#[C:56][Si:57]([CH3:60])([CH3:59])[CH3:58])=[CH:51][CH:50]=2)[CH:42]=1)[OH:11])C1C=CC=CC=1>C(OCC)(=O)C.[OH-].[OH-].[Pd+2]>[OH:11][C@:10]1([C:41]2[CH:46]=[CH:45][C:44]([CH3:47])=[C:43]([CH2:48][C:49]3[CH:50]=[CH:51][C:52]([CH2:55][CH2:56][Si:57]([CH3:60])([CH3:58])[CH3:59])=[CH:53][CH:54]=3)[CH:42]=2)[O:12][C@H:13]([CH2:32][OH:33])[C@@H:14]([OH:24])[C@H:15]([OH:16])[C@H:9]1[OH:8]

Participants

4

Reactant 1

HCID 86600678HCID 86600678, compound

Product 1

HCID 86600680HCID 86600680, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 0.29 g 1-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranos-1-yl)4-methyl-3-[4-(trimethylsilylethynyl)-benzyl]-benzene and 0.25 g of 10% palladium hydroxide on charcoal in 3 ml of ethyl acetate is shaken for 24 h at ambient temperature under a hydrogen pressure of 1 atm. Then another 0.2 g of catalyst are added and the solution is shaken for a further 20 h under a hydrogen atmosphere. Then the catalyst is filtered off, the filtrate is evaporated down and the residue is chromatographed through silica gel (dichloromethane/methanol 1:0->5:1).

Workup

  1. stirringthe solution is shaken for a further 20 h under a hydrogen atmosphere
  2. filtrationThen the catalyst is filtered off
  3. customthe filtrate is evaporated down
  4. customthe residue is chromatographed through silica gel (dichloromethane/methanol 1:0->5:1)

Sources & evidence

ORD record
ord-05b4b3e77cd141cd89ab1149711caf95
Source dataset
uspto-grants-2009_08
Patent number
US07579449B2

Reaction notes

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