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Chemical Structure| 22513-22-0 Chemical Structure| 22513-22-0

Structure of 22513-22-0

Chemical Structure| 22513-22-0

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Product Citations

Product Citations

Thomas Norberg ; Elisabet Kallin ;

Abstract: The human milk trisaccharide 3′- sialyllactose was reacted with an excess of N-methyl-O-benzylhydroxylamine (MBHA) and the product 3′- sialyllactose-MBHA was isolated in high (91%) yield by solid-phase extraction. The isomeric trisaccharide 6′-sialyllactose-MBHA was also prepared, in this case by enzymatic sialylation of lactose-MBHA. A 50/50 mixture of the two sialyllactose-MBHA derivatives was easily separated by reversed-phase HPLC. The free oligosaccharides were recovered from their respective MBHA derivatives by acid hydrolysis.

Keywords: Derivatization ; Milk oligosaccharides ; Hydroxylamines ; Reversed-phase chromatography

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Product Details of [ 22513-22-0 ]

CAS No. :22513-22-0
Formula : C8H11NO
M.W : 137.18
SMILES Code : CNOCC1=CC=CC=C1
English Name :O-Benzyl-N-methylhydroxylamine
MDL No. :MFCD21116670

Safety of [ 22513-22-0 ]

Application In Synthesis of [ 22513-22-0 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 22513-22-0 ]

[ 22513-22-0 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 22513-22-0 ]
  • [ 101555-61-7 ]
  • [ 115364-77-7 ]
YieldReaction ConditionsOperation in experiment
69% With 1-hydroxybenzotriazol-hydrate; triethylamine; dicyclohexyl-carbodiimide In chloroform 1.) 0 deg C, 1 h, 2.) room temperature, overnight;
  • 2
  • [ 22513-22-0 ]
  • [ 482-54-2 ]
  • [ 330457-83-5 ]
YieldReaction ConditionsOperation in experiment
34% With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In tetrahydrofuran; water at 20℃; for 6h;
  • 3
  • [ 22513-22-0 ]
  • [ 38694-48-3 ]
  • [ 1376377-43-3 ]
YieldReaction ConditionsOperation in experiment
65 % With hydrogenchloride; benzotriazol-1-ol; 1,2-dichloro-ethane; triethylamine In dichloromethane; water at 20℃; General procedure 4 for EDC-coupling. General procedure: EDC. HCl (1.3 eq) andHOBt (1 eq) were added to a solution of acid (1 eq) in DCM (0.3 M). Asolution of hydroxylamine (1.3 eq) and Et3N (4 eq) in DCM (0.6 M) wasadded to the first solution and the reaction was allowed to stir overnightat RT. The reaction mixture was further diluted with DCM and washedwith H2O, citric acid (1 M aq. soln.) and brine. The organic layer wasdried over Na2SO4, filtered and concentrated in vacuo. The productswere purified by column chromatography with appropriate eluents.
 

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