5-Aminosalicylic Acid → Glucopyranosylamine

HRID 1371346

Reaktionsgleichung

Reaktionsgleichung von HRID 1371346
[O:1]=[CH:2][C@@H:3]([C@H:5]([C@@H:7]([C@@H:9]([CH2:11][OH:12])[OH:10])[OH:8])[OH:6])O.C(=O)(O)[O-].[NH4+].[NH2:18]C1C=C(C(O)=O)C(O)=CC=1.C(Cl)(Cl)Cl>N1C=CC=CC=1.CO>[C@@H:11]1([NH2:18])[O:12][C@H:3]([CH2:2][OH:1])[C@@H:5]([OH:6])[C@H:7]([OH:8])[C@H:9]1[OH:10]

Komponenten

7

Edukt 4

HCID 40755-Aminosalicylic AcidHCID 6212ChloroformHCID 14013Ammonium BicarbonateHCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal

Produkt 1

HCID 193433Glucopyranosylamine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 1049PyridineLösungsmittel

Versuchsvorschrift

Beta-D-glucosylamine is prepared by the reaction of D-(+)-glucose with ammonium bicarbonate as described by Likhosherstov, L. M. et al. (Carbohydr. Res. 146: C1, 1986). A reaction mixture containing the glycosylamine and a 1- to 2-fold excess by weight of 5-aminosalicylic acid is allowed to react overnight in pyridine at 50° C. The reaction is monitored by thin-layer chromatography (TLC) (silica gel; eluent: CHCl3:MeOH, 1:1, by volume). The solvent is removed, and the reaction mixture is purified by chromatography on silica gel or BIOGEL-F2™ (BioRad, Richmond, Calif.), using absorbance at 254 nm as detection. The products are characterized by TLC on silica gel, electrospray mass spectrometry, and 1H- and 13C-NMR analysis. The transamination reaction is indicated by a downfield shift of resonance of the anomeric proton (observed at δ=4.1 ppm by analysis of the unsubstituted glycosyl-1-amine) to δ=4.3–4.7 ppm in the 1H-NMR spectrum of the β-anomer of the synthetic glycoconjugate product. (This anomer is the major product of the transamination reaction.)

Aufarbeitung

  1. customThe solvent is removed
  2. customthe reaction mixture is purified by chromatography on silica gel or BIOGEL-F2™ (BioRad, Richmond, Calif.)
  3. customThe transamination reaction
  4. customthe major product of the transamination reaction

Quellen und Nachweise

ORD-Eintrag
ord-d32a83443cc04f33b3ec521ca4cfe7ab
Quelldatensatz
uspto-grants-2007_01
Patentnummer
US07157444B2

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