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

HRID 1450361Notes

Reaction equation

HRID 1450361 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, compoundYield 96.2%

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.) for 2.5 hours. The mixture is filtered through diatomaceous earth, washed with ethyl acetate and ethyl alcohol, and concentrated in vacuo to give 0.460 g of the desired product.

Workup

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

Sources & evidence

ORD record
ord-29a33b99a75040c3b4c5868a708ae4db
Source dataset
uspto-grants-1997_02
Patent number
US05602118

Reaction notes

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