Water → N-Acetyl-D-Galactosamine

HRID 1772314Notes

Reaction equation

HRID 1772314 reaction equation
C[Si](C)(C)CC[O:5][C:6](=[O:12])[CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].C1COCC1.[OH2:20].[OH2:21].[OH2:22].[F-].[CH2:24]([N+:28](CCCC)(CCCC)CCCC)[CH2:25]CC.[OH2:41]>C(#N)C>[OH:12][CH:6]1[O:5][C@H:10]([CH2:11][OH:22])[C@H:9]([OH:21])[C@H:8]([OH:20])[C@H:7]1[NH:28][C:24]([CH3:25])=[O:41]

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 131734665HCID 131734665, compound

Product 1

HCID 35717N-Acetyl-D-Galactosamine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The above compound was prepared as above using (S)-2-amino-6-(E)-hexadec-8-enoylamino)-hexanoic acid 2-trimethylsilanyl-ethyl ester and cleaving the protecting group as follows: After the penultimate step, the resultant 2-trimethylsilanyl-ethyl ester (245 mg, 0.107 mmol, Eq: 1.00) was combined with THF abs, (5 mL) to give a colorless solution. Tetrabutyl-ammonium fluoride trihydrate (168 mg, 0.533 mmol, Eq: 5.00) was added at 0° C. and the reaction was stored in the fridge over night. Pouring onto crushed ice, extraction with ethyl acetate, washing with water, drying over Na2SO4, and evaporation of all solvents yielded a sticky oil. Dissolution in acetonitrile and water and lyophilization afforded eventually 0.120 g of the title compound as white solid, MS (ISP): 112.5 [M+2Na]2+/2.

Workup

  1. customThe above compound was prepared as
  2. customto give a colorless solution
  3. waitthe reaction was stored in the fridge over night
  4. additionPouring
  5. customonto crushed
  6. extractionice, extraction with ethyl acetate
  7. washwashing with water
  8. dry with materialdrying over Na2SO4, and evaporation of all solvents
  9. customyielded a sticky oil

Sources & evidence

ORD record
ord-06a5bd87cd68454ea2b4d1b14c7fbd71
Source dataset
uspto-grants-2016_02
Patent number
US09249179B2

Reaction notes

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