5-Aminosalicylic Acid → Glucopyranosylamine

HRID 1371346

반응식

HRID 1371346 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

HCID 193433Glucopyranosylamine

시약·촉매·용매 2

HCID 887Methanol용매HCID 1049Pyridine용매

실험 절차

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.)

후처리

  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

출처 및 근거

ORD 기록
ord-d32a83443cc04f33b3ec521ca4cfe7ab
출처 데이터셋
uspto-grants-2007_01
특허 번호
US07157444B2

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