Stereocontrolled 1,2-trans-arabinofuranosylation in the absence of 2-O-acyl group in glycosyl donor

Stereocontrolled 1,2-trans-arabinofuranosylation in the absence of 2-O-acyl group in glycosyl donor Full article

Journal

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

Output data

Year: 2024, Volume: 544, Article number : 109252, Pages count : DOI: 10.1016/j.carres.2024.109252

Authors

Abronina Polina I ¹ , Novikov Dmitry S ¹ , Malysheva Nelly N 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. Electronic address: polina-abronina@yandex.ru.

Stereocontrolled 1,2-trans-α-arabinofuranosylation using polysilylated mono- and disaccharide glycosyl donors was investigated. A complete α-stereoselectivity of 1,2-trans-arabinofuranosylation was found for Ara-β-(1 → 2)-Ara disaccharide glycosyl donors containing five triisopropylsilyl (TIPS) groups with arylthiol (1) (as shown in our previous publications) or N-phenyltrifluoroacetimidoyl (2) (this work) leaving groups. Conversely, in case of monosaccharide thioglycosides polysilylated with acyclic silyl groups (TIPS, TBDPS), stereoselectivity of glycosylation was lower (α:β = 7–8:1), although the desired α-isomer still dominated. Disaccharide glycosyl donor 2 was successfully used in the synthesis of linear α-(1 → 5)-, β-(1 → 2)-linked hexaarabinofuranoside useful for further preparation of conjugates thereof as antigens valuable for the diagnosis of mycobacterioses.

Abronina P.I. , Novikov D.S. , Malysheva N.N. , Zinin A.I. , Chizhov A.O. , Kononov L.O.
Stereocontrolled 1,2-trans-arabinofuranosylation in the absence of 2-O-acyl group in glycosyl donor
Carbohydrate Research. 2024. V.544. 109252 . DOI: 10.1016/j.carres.2024.109252 WOS Scopus OpenAlex

Web of science:	WOS:001307873800001
Scopus:	2-s2.0-85202570289
OpenAlex:	W4402034603

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