Stereocontrolling Effect of a Single Triisopropylsilyl Group in 1,2‐cis‐Glucosylation

Stereocontrolling Effect of a Single Triisopropylsilyl Group in 1,2‐cis‐Glucosylation Full article

Journal

European Journal of Organic Chemistry
ISSN: 1434-193X , E-ISSN: 1099-0690

Output data

Year: 2022, Volume: 2022, Number: 39, Article number : e202200517, Pages count : DOI: 10.1002/ejoc.202200517

Authors

Abronina Polina I. ¹ , Malysheva Nelly N. ¹ , Zinin Alexander I. ¹ , Kolotyrkina Natalya G. ¹ , Kononov Leonid O. ¹

Affiliations

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

Glycosylation with phenyl 3,4,6-tri-O-benzoyl-2-O-triisopropylsilyl (TIPS)-1-thio-β-d-glucopyranoside is highly 1,2-cis-stereoselective, while the use of 2,3-di-O-TIPS glucosyl donor with benzoyl groups at O-4 and O-6 results in the loss of α-stereoselectivity (α/β=3 : 1). Complete α-stereocontrol with 2-O-TIPS substituted glucosyl donors could only be achieved in glucosylation of weak nucleophiles. In this case, the glucosylation seems to proceed along the SN1-like pathway via the 4H3 conformer of glycosyl cation stabilized by the bulky TIPS group at O-2.

Abronina P.I. , Malysheva N.N. , Zinin A.I. , Kolotyrkina N.G. , Kononov L.O.
Stereocontrolling Effect of a Single Triisopropylsilyl Group in 1,2‐cis‐Glucosylation
European Journal of Organic Chemistry. 2022. V.2022. N39. e202200517 . DOI: 10.1002/ejoc.202200517 WOS Scopus OpenAlex

Web of science:	WOS:000826659300001
Scopus:	2-s2.0-85135077070
OpenAlex:	W4283652509

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