2,4-anhydro-3,5-bis-O-(phenylmethyl)-D-lyxonic acid methyl ester → HCID 15725611, compound

HRID 1600162Notes

Reaction equation

HRID 1600162 reaction equation
[CH3:1][O:2][C:3]([C@H:5]1[O:16][C@H:15]([CH2:17][O:18]CC2C=CC=CC=2)[C@@H:6]1[O:7]CC1C=CC=CC=1)=[O:4].[H][H]>[OH-].[OH-].[Pd+2].CO>[CH3:1][O:2][C:3]([C@H:5]1[O:16][C@H:15]([CH2:17][OH:18])[C@@H:6]1[OH:7])=[O:4]

Participants

5

Reactant 2

HCID 147595602,4-anhydro-3,5-bis-O-(phenylmethyl)-D-lyxonic acid methyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 15725611HCID 15725611, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A slurry of 1.01 g of 2,4-anhydro-3,5-bis-O-(phenylmethyl)-D-lyxonic acid methyl ester (prepared by the procedure in Tetrahedron Letters, Vol 31, No. 33, p4787, 1990), 0.253 g of palladium hydroxide on carbon, and 30 ml of methyl alcohol is hydrogenated under a balloon of hydrogen (1 atm.) for2.5 hours. The mixture is filtered through diatomaceous earth, washed with ethyl acetate and ethyl alcohol, and concentrated in vacuo to give 0.460 gof the desired product.

Workup

  1. custom5 hours
  2. filtrationThe mixture is filtered through diatomaceous earth
  3. washwashed with ethyl acetate and ethyl alcohol
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cee4c68e87244b10ab4ca44da5a48200
Source dataset
uspto-grants-1998_04
Patent number
US05744465

Reaction notes

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