Oxocarbenium ion cyclizations for the synthesis of disaccharide mimetics of 2-amino-2-deoxy-pyranosides: Application to the carbasugar of β-galactosamine-(1,4)-3-O-methyl-D-chiro-inositol.
4-C-Lyxose
Carbadisaccharide
Galactosamine
Glycomimetic
Inositol
Insulin
Journal
Carbohydrate research
ISSN: 1873-426X
Titre abrégé: Carbohydr Res
Pays: Netherlands
ID NLM: 0043535
Informations de publication
Date de publication:
Aug 2022
Aug 2022
Historique:
received:
18
03
2022
revised:
14
05
2022
accepted:
16
05
2022
pubmed:
2
6
2022
medline:
22
6
2022
entrez:
1
6
2022
Statut:
ppublish
Résumé
The synthesis of the carbasugar of β-galactosamine-(1,4)-3-O-methyl-D-chiro-inositol (INS-2), a potential tool for studying glucose metabolism, is described. The synthetic strategy, entails an oxocarbenium ion cyclization on a chiro-inositol derived, thioacetal-enol ether to give a carbocyclic enol ether, which is elaborated to the 2-amino-2-deoxy carbasugar framework via a 2-oximo derivative.
Identifiants
pubmed: 35643049
pii: S0008-6215(22)00096-9
doi: 10.1016/j.carres.2022.108595
pii:
doi:
Substances chimiques
Carbasugars
0
Disaccharides
0
Ethers
0
Inositol
4L6452S749
Galactosamine
7535-00-4
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
108595Informations de copyright
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