Hydrochloric Acid → 2-Amino-2-deoxy-4-O-beta-D-galactopyranosyl-D-glucose

HRID 222520Notes

Reaction equation

HRID 222520 reaction equation
C([N:8](C(OCC1C=CC=CC=1)=O)[C@@H:9]1[C@@H:15]([OH:16])[C@H:14]([O:17][C@@H:18]2[O:26][C@H:25]([CH2:27][OH:28])[C@H:23]([OH:24])[C@H:21]([OH:22])[C@H:19]2[OH:20])[C@@H:13]([CH2:29][OH:30])[O:12][CH:10]1[OH:11])C1C=CC=CC=1.Cl>CO.[Pd]>[OH:11][CH:10]1[O:12][C@H:13]([CH2:29][OH:30])[C@@H:14]([O:17][C@@H:18]2[O:26][C@H:25]([CH2:27][OH:28])[C@H:23]([OH:24])[C@H:21]([OH:22])[C@H:19]2[OH:20])[C@H:15]([OH:16])[C@H:9]1[NH2:8]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 131729791N-benzyl,N-benzyloxycarbonyl lactosamine

Product 1

HCID 114732932-Amino-2-deoxy-4-O-beta-D-galactopyranosyl-D-glucoseYield 82.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

N-benzyl,N-benzyloxycarbonyl lactosamine (200 mg) was dissolved in MeOH (30 mL) and HCl in MeOH (400 μL, 1.4 mmol/mL) added to the mixture followed by addition of Pd/C (50 mg) and stirred under H2 (20 bar) for 8 h. The catalyst filtered off and the filtrate concentrated affording lactosamine (100 mg) as a white powder.

Workup

  1. filtrationThe catalyst filtered off
  2. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-26fdf96975d140a79afb86833aa7cf44
Source dataset
uspto-grants-2012_06
Patent number
US08207328B2

Reaction notes

Loading…