HCID 69032396, compound → HCID 86605613, compound

HRID 238899Notes

Reaction equation

HRID 238899 reaction equation
C([O:8][CH:9](O)[C@:10]([O:32][Si:33]([C:36]([CH3:39])([CH3:38])[CH3:37])([CH3:35])[CH3:34])([OH:31])[C@@:11]([O:23][Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25])([OH:22])[CH:12]([O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16])[OH:13])C1C=CC=CC=1>CCOC(C)=O.[Pd]>[Si:15]([O:14][CH:12]([OH:13])[C@@:11]([O:23][Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:25])[CH3:26])([C@:10]([O:32][Si:33]([C:36]([CH3:37])([CH3:38])[CH3:39])([CH3:35])[CH3:34])([CH2:9][OH:8])[OH:31])[OH:22])([C:18]([CH3:21])([CH3:19])[CH3:20])([CH3:17])[CH3:16]

Participants

4

Reactant 1

HCID 69032396HCID 69032396, compound

Product 1

HCID 86605613HCID 86605613, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

4-Benzyloxy-1,2,3-tri(tert-butyldimethylsilyloxy)-L-threitol (5.9 g, 10.6 mmol) dissolved in EtOAc (70 mL) was hydrogenated (balloon as H2 container) in the presence of 10% Pd/C (1 g) until no more starting material could be detected on TLC plate (about 5 h). The catalyst was removed by filtration through a Celite pad, with rinsing the solid with EtOAc. The filtrate was evaporated to dryness, and the residue was purified by silica gel flash chromatography (eluting with 10% ether in hexanes) to give 1,2,3-tri(tert-butyldimethylsilyloxy)-L-threitol (2.1 g, 41% yield).

Workup

  1. customcould be detected on TLC plate (about 5 h)
  2. customThe catalyst was removed by filtration through a Celite pad
  3. washwith rinsing the solid with EtOAc
  4. customThe filtrate was evaporated to dryness
  5. customthe residue was purified by silica gel flash chromatography (eluting with 10% ether in hexanes)

Sources & evidence

ORD record
ord-53a2ae337fba4f959c2af386a58f80c0
Source dataset
uspto-grants-2014_02
Patent number
US08642644B2

Reaction notes

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