HCID 86752795, compound → HCID 86752794, compound

HRID 355480Notes

Reaction equation

HRID 355480 reaction equation
[CH2:1]([C@@:8]1([O:22][C@H:21]([CH2:23][NH:24][C:25]([C@@H:27]([C@H:32]([C@@H:37]([C@@H:42]([CH2:47][O:48][C:49](=[O:51])[CH3:50])[O:43][C:44](=[O:46])[CH3:45])[O:38][C:39](=[O:41])[CH3:40])[O:33][C:34](=[O:36])[CH3:35])[O:28][C:29](=[O:31])[CH3:30])=[O:26])[C@@H:16]([O:17][C:18](=[O:20])[CH3:19])[C@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@H:10]1[NH:52]C(OCC1C=CC=CC=1)=O)[OH:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>O1CCOCC1.O.[Pd]>[CH2:1]([C@@:8]1([O:22][C@H:21]([CH2:23][NH:24][C:25]([C@@H:27]([C@H:32]([C@@H:37]([C@@H:42]([CH2:47][O:48][C:49](=[O:51])[CH3:50])[O:43][C:44](=[O:46])[CH3:45])[O:38][C:39](=[O:41])[CH3:40])[O:33][C:34](=[O:36])[CH3:35])[O:28][C:29](=[O:31])[CH3:30])=[O:26])[C@@H:16]([O:17][C:18](=[O:20])[CH3:19])[C@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@H:10]1[NH2:52])[OH:9])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 1

HCID 86752795HCID 86752795, compound

Product 1

HCID 86752794HCID 86752794, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 250 mg of 2,3,4,5,6-penta-O-acetyl-D-gluconic acid (benzyl 3,4-di-O-acetyl-2-benzyloxycarbonylamino-2,6-didesoxy-a-D-glucopyranosid-6-yl)-amide in 20 ml of dioxan and 2 ml water was hydrogenated at room temperature in the presence of palladium on charcoal (10%). After 2 hours, the catalyst was filtered off over a filter aid and the filtrate was concentrated. The residue was crystallized from ethyl acetate/ether and gave 2,3,4,5,6-penta-O-acetyl-D-gluconic acid (benzyl 3,4-di-O-acetyl-2-amino-2,6-didesoxy-a-D-glucopyranosid-6-yl)-amide, [a]+96.0° (c 0.2; dioxan), MS: m/z 741.1 ([M+H]+).

Workup

  1. filtrationthe catalyst was filtered off over a filter aid
  2. concentrationthe filtrate was concentrated
  3. customThe residue was crystallized from ethyl acetate/ether

Sources & evidence

ORD record
ord-085f47ded0d74a2da00d9ff03a3f112f
Source dataset
uspto-grants-1998_11
Patent number
US05830920

Reaction notes

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