HCID 11071586, compound → HCID 10874012, compound

HRID 1708341Notes

Reaction equation

HRID 1708341 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-e4568eada14e4fba9034483635f103dc
Source dataset
uspto-grants-1994_10
Patent number
US05358859

Reaction notes

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