TIPS group-assisted isomerization of benzyl protected d-manno- and d-glucopyranose to d-fructofuranose derivatives

TIPS group-assisted isomerization of benzyl protected d-manno- and d-glucopyranose to d-fructofuranose derivatives Full article

Journal

Carbohydrate Research
ISSN: 1873-426X , E-ISSN: 0008-6215

Output data

Year: 2023, Volume: 534, Article number : 108942, Pages count : DOI: 10.1016/j.carres.2023.108942

Authors

Karpenko Maxim Y. ¹ , Abronina Polina I. ¹ , Zinin Alexander I. ¹ , Chizhov Alexander O. ¹ , Kononov Leonid O. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences, Leninsky Prosp. 47, 119991, Moscow, Russian Federation

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.

Karpenko M.Y. , Abronina P.I. , Zinin A.I. , Chizhov A.O. , Kononov L.O.
TIPS group-assisted isomerization of benzyl protected d-manno- and d-glucopyranose to d-fructofuranose derivatives
Carbohydrate Research. 2023. V.534. 108942 . DOI: 10.1016/j.carres.2023.108942 WOS Scopus OpenAlex

Web of science:	WOS:001084143600001
Scopus:	2-s2.0-85171994040
OpenAlex:	W4386885503

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