Chemical transformation of lactose into 4- O-β- d-galactopyranosyl- d-glucuronic acid (pseudolactobiouronic acid) and some derivatives thereof

Chemical transformation of lactose into 4- O-β- d-galactopyranosyl- d-glucuronic acid (pseudolactobiouronic acid) and some derivatives thereof

The selective oxidation of the primary alcoholic function of the reducing unit of lactose was achieved in good overall yield (67%) starting from 2′,6′-di- O-benzyl-2,3:3′,4′-di- O-isopropylidenelactose dimethyl acetal ( 1) through a simple multi-step procedure based on the selective acetylation of O...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Carbohydrate research 2002-06, Vol.337 (11), p.991-996
Hauptverfasser: Attolino, Emanuele, Catelani, Giorgio, D'Andrea, Felicia, Puccioni, Leonardo
Format: Artikel
Sprache:eng
Schlagworte:
Acetylation
Carbohydrate Sequence
Glucuronates
Glucuronic Acid - chemical synthesis
Lactose
Lactose - chemistry
Molecular Sequence Data
Oxidations
Pseudoaldobiouronic acids
Pseudolactobiouronic acid
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
Beschreibung
Zusammenfassung:The selective oxidation of the primary alcoholic function of the reducing unit of lactose was achieved in good overall yield (67%) starting from 2′,6′-di- O-benzyl-2,3:3′,4′-di- O-isopropylidenelactose dimethyl acetal ( 1) through a simple multi-step procedure based on the selective acetylation of OH-5 of 1 (methoxyisopropylation, acetylation, de-methoxyisopropylation) followed by a two-step oxidation at C-6 (TPAP-NMO then TEMPO-NaOCl) and finally, complete removal of the protecting groups. Graphic
ISSN:0008-6215
1873-426X
DOI:10.1016/S0008-6215(02)00084-8