Five Triisopropylsilyl Substituents in Ara‐β‐(1→2)‐Ara Disaccharide Glycosyl Donor Make Unselective Glycosylation Reaction Stereoselective Full article
| Journal |
European Journal of Organic Chemistry
ISSN: 1434-193X , E-ISSN: 1099-0690 |
||||
|---|---|---|---|---|---|
| Output data | Year: 2022, Volume: 2022, Number: 46, Article number : e202201110, Pages count : DOI: 10.1002/ejoc.202201110 | ||||
| Authors |
|
||||
| Affiliations |
|
Abstract:
Formation of 1,2-trans-arabinofuranoside linkage in arabinans from Mycobacterium tuberculosis using differently protected Ara-β-(1→2)-Ara disaccharide glycosyl donors in the absence of a participating group at O-2 was studied. The influence of the nature of the protective and leaving groups in glycosyl donors on the efficiency and stereoselectivity of the 1,2-trans-arabinofuranosylation was investigated. The efficiency of Ara-β-(1→2)-Ara p-tolyl thioglycoside containing five triisopropylsilyl groups in 1,2-trans-stereoselective synthesis of a protected tetrasaccharide corresponding to a fragment of the M. tuberculosis arabinan was shown for the first time. On the contrary, the use of glycosyl donors based on Ara-β-(1→2)-Ara containing only benzoyl or both silyl and benzoyl groups led to the loss of stereocontrol.
Cite:
Abronina P.I.
, Malysheva N.N.
, Stepanova E.V.
, Shvyrkina J.S.
, Zinin A.I.
, Kononov L.O.
Five Triisopropylsilyl Substituents in Ara‐β‐(1→2)‐Ara Disaccharide Glycosyl Donor Make Unselective Glycosylation Reaction Stereoselective
European Journal of Organic Chemistry. 2022. V.2022. N46. e202201110 . DOI: 10.1002/ejoc.202201110 WOS Scopus OpenAlex
Five Triisopropylsilyl Substituents in Ara‐β‐(1→2)‐Ara Disaccharide Glycosyl Donor Make Unselective Glycosylation Reaction Stereoselective
European Journal of Organic Chemistry. 2022. V.2022. N46. e202201110 . DOI: 10.1002/ejoc.202201110 WOS Scopus OpenAlex
Identifiers:
| Web of science: | WOS:000896671500001 |
| Scopus: | 2-s2.0-85143901910 |
| OpenAlex: | W4308501649 |