HCID 131736872, compound → HCID 69865256, compound

HRID 1488298Notes

Reaction equation

HRID 1488298 reaction equation
C(OC(=O)[NH:10][CH2:11][CH2:12][O:13][C@@H:14]1[O:22][C@H:21]([CH2:23][OH:24])[C@@H:19]([OH:20])[C@H:17]([OH:18])[C@@H:15]1[OH:16])C1C=CC=CC=1>O.[Pd]>[O:13]([CH2:12][CH2:11][NH2:10])[C@@H:14]1[O:22][C@H:21]([CH2:23][OH:24])[C@@H:19]([OH:20])[C@H:17]([OH:18])[C@@H:15]1[OH:16]

Participants

4

Reactant 1

HCID 131736872HCID 131736872, compound

Product 1

HCID 69865256HCID 69865256, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

A mixture of benzyl[2-(β-D-mannopyranosyloxy)ethyl]carbamate (133 mg, 0.372 mmol), and Pd/C (20 mg, 0.019 mmol) in water (5 mL) was allowed to stir under a balloon of H2 at rt for 4 hr. The catalyst was filtered off and washed with H2O (3×5 mL). The fitrate was concentrated to give the title compound. 1H NMR (CD3OD) δ 4.53-4.52 (1H, m), 3.93-3.85 (3H, m), 3.72-3.64 (2H, m), 3.53-3.49 (1H, m), 3.44-3.42 (1H, m), 3.22-3.18 (1H, m), 2.92-2.85 (2H, m).

Workup

  1. filtrationThe catalyst was filtered off
  2. washwashed with H2O (3×5 mL)
  3. concentrationThe fitrate was concentrated

Sources & evidence

ORD record
ord-a0e7648e356c490c83fd0bed93541282
Source dataset
uspto-grants-2016_08
Patent number
US09427475B2

Reaction notes

Loading…