Methanol → N-(1-deoxyfructopyranos-1-yl)-D-isoleucine

HRID 1463774

Reaktionsgleichung

Reaktionsgleichung von HRID 1463774
CO.[NH2:3][C@@H:4]([C:9]([OH:11])=[O:10])[C@@H:5]([CH2:7][CH3:8])[CH3:6].[O:12]=[CH:13][C@@H:14]([C@H:16]([C@@H:18]([C@@H:20]([CH2:22]O)[OH:21])[OH:19])[OH:17])[OH:15]>N1C=CC=CC=1>[CH2:22]([NH:3][C@@H:4]([C:9]([OH:11])=[O:10])[C@@H:5]([CH2:7][CH3:8])[CH3:6])[C:20]1([O:12][CH2:13][C@@H:14]([OH:15])[C@@H:16]([OH:17])[C@@H:18]1[OH:19])[OH:21]

Komponenten

5

Edukt 3

HCID 887MethanolHCID 76551D-IsoleucineHCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal

Produkt 1

HCID 86747745N-(1-deoxyfructopyranos-1-yl)-D-isoleucineAusbeute 49,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

A dry mixture of 40 ml of methanol and 10 ml of pyridine was added to 100 mg of dry D-isoleucine together with 300 mg of anhydrous glucose, and reaction and purification were carried out as described in Example 9, but making use of smaller-volume chromatography columns. Crystallization of the final product yielded 110 mg of N-(1-deoxyfructopyranos-1-yl)-D-isoleucine. Melting point 142°-144° C.

Aufarbeitung

  1. customCrystallization of the final product

Quellen und Nachweise

ORD-Eintrag
ord-811538b30e2940988f965e6fd7175727
Quelldatensatz
uspto-grants-1994_04
Patentnummer
US05302582

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