TIPS group-assisted isomerization of benzyl protected d-manno- and d-glucopyranose to d-fructofuranose derivatives.
Isomerization
Triisopropylsilyl group
d-fructofuranose
d-glucopyranose
d-mannopyranose
Journal
Carbohydrate research
ISSN: 1873-426X
Titre abrégé: Carbohydr Res
Pays: Netherlands
ID NLM: 0043535
Informations de publication
Date de publication:
Dec 2023
Dec 2023
Historique:
received:
13
06
2023
revised:
07
09
2023
accepted:
11
09
2023
medline:
7
12
2023
pubmed:
29
9
2023
entrez:
28
9
2023
Statut:
ppublish
Résumé
Base-promoted (MeONa in MeOH or imidazole in DMF) isomerization of a series of 3,4,6-tri-O-benzyl-d-gluco- and d-mannopyranose derivatives with triisopropylsilyl (TIPS) substituents was studied. The presence of a bulky TIPS group at O-1 or O-2 was shown to be favorable for the isomerization of benzyl protected d-gluco- and d-mannopyranose derivatives to d-fructofuranose derivatives, in which the bulky silyl group occupies less sterically hindered primary position. The highest yield (33%) of the fructofuranose derivative was achieved when 3,4,6-tri-O-benzyl-2-O-triisopropylsilyl-d-mannopyranose was treated with MeONa in MeON at 50 °C.
Identifiants
pubmed: 37769375
pii: S0008-6215(23)00204-5
doi: 10.1016/j.carres.2023.108942
pii:
doi:
Substances chimiques
Mannose
PHA4727WTP
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
108942Informations de copyright
Copyright © 2023 Elsevier Ltd. All rights reserved.
Déclaration de conflit d'intérêts
Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.