4-nitrophenyl 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl)-beta-D-glucopyranoside → 4-Aminophenyl 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl)-beta-D-glucopyranoside

HRID 435510Notes

Reaction equation

HRID 435510 reaction equation
[C:1]([O:4][C@@H:5]1[C@@H:20]([O:21][C:22](=[O:24])[CH3:23])[C@H:19]([O:25][C@H:26]2[O:43][C@H:42]([CH2:44][O:45][C:46](=[O:48])[CH3:47])[C@@H:37]([O:38][C:39](=[O:41])[CH3:40])[C@H:32]([O:33][C:34](=[O:36])[CH3:35])[C@H:27]2[O:28][C:29](=[O:31])[CH3:30])[C@@H:18]([CH2:49][O:50][C:51](=[O:53])[CH3:52])[O:17][C@H:6]1[O:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][CH:9]=1)(=[O:3])[CH3:2]>C(O)(=O)C.[Pd]>[C:1]([O:4][C@@H:5]1[C@@H:20]([O:21][C:22](=[O:24])[CH3:23])[C@H:19]([O:25][C@H:26]2[O:43][C@H:42]([CH2:44][O:45][C:46](=[O:48])[CH3:47])[C@@H:37]([O:38][C:39](=[O:41])[CH3:40])[C@H:32]([O:33][C:34](=[O:36])[CH3:35])[C@H:27]2[O:28][C:29](=[O:31])[CH3:30])[C@@H:18]([CH2:49][O:50][C:51](=[O:53])[CH3:52])[O:17][C@H:6]1[O:7][C:8]1[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 132065704-nitrophenyl 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl)-beta-D-glucopyranoside

Product 1

HCID 132065724-Aminophenyl 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl)-beta-D-glucopyranoside

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

To 27.4 g of 4-nitrophenyl 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-β-D-glucopyranoside suspended in 150 ml of acetic acid was added 2.7 g of 10% palladium-on-charcoal catalyst in a Parr hydrogenation bottle, and this was hydrogenated on a Parr hydrogenator for 17 hours. The catalyst was filtered from the solution through diatomaceous earth and washed thoroughly with methanol. The solvents were evaporated in vacuo. The residue was dissolved in one liter of toluene and again evaporated. The residue was dissolved in methylene chloride and passed through a pad of magnesium silicate and the solvent was evaporated to yield the title compound as a light yellow oil. A 3.5 g portion of this was crystallized from methanol to yield 2.6 g of an off-white crystal, m.p. 173°-175° C.

Workup

  1. filtrationThe catalyst was filtered from the solution through diatomaceous earth
  2. washwashed thoroughly with methanol
  3. customThe solvents were evaporated in vacuo
  4. dissolutionThe residue was dissolved in one liter of toluene
  5. customagain evaporated
  6. dissolutionThe residue was dissolved in methylene chloride
  7. customthe solvent was evaporated

Sources & evidence

ORD record
ord-6af40fdb75df4367a180184cc1cbd93a
Source dataset
uspto-grants-1983_08
Patent number
US04401661

Reaction notes

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