HCID 67930855, compound → HCID 67930799, compound

HRID 728205Notes

Reaction equation

HRID 728205 reaction equation
C([O:8][C@@H:9]1[C@H:14]2[CH2:15][O:16][C@H:12]([O:13]2)[C@H:11]([O:17][CH3:18])[CH2:10]1)C1C=CC=CC=1.[H][H]>C(O)C.[Pd]>[CH3:18][O:17][C@@H:11]1[CH2:10][C@H:9]([OH:8])[C@H:14]2[CH2:15][O:16][C@@H:12]1[O:13]2

Participants

5

Reactant 2

HCID 67930855HCID 67930855, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 67930799HCID 67930799, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

A solution of 1,6-anhydro-4-O-benzyl-3-deoxy-2-O-methyl-β-D-ribo-hexopyranose (see Example 3(1)) (4.5 g) in ethanol (20 ml) was added to a suspension of 10% palladium on carbon (0.2 g) in ethanol (50 ml) and the resulting mixture was stirred in a hydrogen atmosphere until uptake of hydrogen had ceased (5 hours). Celite was added and the mixture was filtered through two layers of glass fibre filter paper. The filtrate was concentrated to give a quantitative yield of the title compound as a colourless syrup which crystallised spontaneously. Filtration with the aid of a little hexane gave 2.52 g (88% yield) of crystalline title compound, m.p. 67°-68° C.; [α]D -87.2°.

Workup

  1. custom(5 hours)
  2. additionCelite was added
  3. filtrationthe mixture was filtered through two layers of glass fibre filter paper
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-ac4b4a20b65445f8ba35f21eec71a001
Source dataset
uspto-grants-1991_09
Patent number
US05047518

Reaction notes

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