HCID 11071586, compound → HCID 10874012, compound

HRID 1421842Notes

Reaction equation

HRID 1421842 reaction equation
[C:1]([O:4][C@:5]1([O:28][C@H:27]([C@@H:29]([CH2:34][O:35][C:36](=[O:38])[CH3:37])[O:30][C:31](=[O:33])[CH3:32])[C@H:22]([O:23][C:24](=[O:26])[CH3:25])[C@H:17]([O:18][C:19](=[O:21])[CH3:20])[CH2:16]1)[C:6]([O:8]CC1C=CC=CC=1)=[O:7])(=[O:3])[CH3:2]>C(O)C.[Pd]>[C:1]([O:4][C@:5]1([O:28][C@H:27]([C@@H:29]([CH2:34][O:35][C:36](=[O:38])[CH3:37])[O:30][C:31](=[O:33])[CH3:32])[C@H:22]([O:23][C:24](=[O:26])[CH3:25])[C@H:17]([O:18][C:19](=[O:21])[CH3:20])[CH2:16]1)[C:6]([OH:8])=[O:7])(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 11071586HCID 11071586, compound

Product 1

HCID 10874012HCID 10874012, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 20b (220 mg, 0.41 mmol) and Pd-C (10%, 55 mg) in ethanol (3 mL) was vigorously stirred under H2 at room temperature for 1 h. After the catalyst was filtered off, the filtrate was concentrated in vacuo. The residue was recrystallized from diethyl ether to give 20a (177 mg, 97%) as fine needles, mp 132-133° C.; [α]25D+374° (c 0.88, CHCl3). Its 1H NMR spectrum (C6D6) was identical with that reported previously by Unger et al. (Carbohydr. Res. 1980, 80, 191).

Workup

  1. filtrationAfter the catalyst was filtered off
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was recrystallized from diethyl ether

Sources & evidence

ORD record
ord-79f51768d7254cea9bf12bf2132dab14
Source dataset
uspto-grants-2000_06
Patent number
US06080563

Reaction notes

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