Water → alpha-D-Galactopyranose

HRID 2184651

Reaction equation

HRID 2184651 reaction equation
[C@@H:1]1([O:12][C@H]2[C@@H](O)[C@@H](CO)O[C@H](OC3C=CC(N)=CC=3)[C@@H]2O)[O:9][C@H:8]([CH2:10][OH:11])[C@H:6]([OH:7])[C@H:4]([OH:5])[C@H:2]1[OH:3].C([O-])(O)=O.[Na+].O>O.CC#N>[OH:12][C@H:1]1[O:9][C@H:8]([CH2:10][OH:11])[C@H:6]([OH:7])[C@H:4]([OH:5])[C@H:2]1[OH:3]

Participants

5

Reactant 3

HCID 962WaterHCID 516892Sodium BicarbonateHCID 69753278p-aminophenyl 3-O-beta-D-galactopyranosyl-alpha-D-galactopyranoside

Product 1

HCID 439357alpha-D-GalactopyranoseYield 102.1%

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

A mixture of p-aminophenyl 3-O-α-D-galactopyranosyl-α-D-galactopyranoside 22 (11 mg, 0.025 mmol), tetrameric platform 28, and NaHCO3 (3 mg, 0.030 mmol) in 0.15 mL of H2O/CH3CN (1:1) was slightly shaken for 1 h. After addition of 0.15 mL of H2O, the reaction mixture was set at room temperature for 2 d and purified on reversed phase HPLC column eluted at 1 mL/min with a gradient of acetonitrile-water (0 to 30%) over 15 minutes to yield 41 (4.6 mg, 40%) as a white solid: MS (ESI): m/e (M/2+1) Calcd. for C60H95N7O29: 1377.6 obsd: 1377.9.

Workup

  1. waitthe reaction mixture was set at room temperature for 2 d
  2. custompurified on reversed phase HPLC column
  3. washeluted at 1 mL/min with a gradient of acetonitrile-water (0 to 30%) over 15 minutes

Sources & evidence

ORD record
ord-2b4df7ca20394a138fdb55fe1fae365a
Source dataset
uspto-grants-2002_06
Patent number
US06399578B1

Linked notes

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