Thio-click reaction of 2-deoxy-exo-glycals towards new glycomimetics: stereoselective synthesis of C-2-deoxy-D-glycopyranosyl compounds

A series of 2-deoxy-glycopyranosyl cyanides with D-arabino, D-lyxo, D-erythro, and D-threo configurations was synthesized from the corresponding glycals via 2-deoxy-glycopyranosyl acetates. The cyanides were transformed to anhydro-aldose tosylhydrazones by reduction with NaH2PO2/Ra-Ni in the presenc...

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Bibliographic Details
Published inNew journal of chemistry Vol. 43; no. 15; pp. 5670 - 5686
Main Authors Jozsef, Janos, Juhasz, Laszlo, Somsak, Laszlo
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 2019
Royal Society of Chemistry
Subjects
Acetates
Chemical reactions
Chemical synthesis
Chemistry
Chemistry, Multidisciplinary
Cyanides
Disaccharides
Physical Sciences
Science & Technology
Stereoselectivity
ROUTE
ANHYDRO-ALDOSE TOSYLHYDRAZONES
ENE REACTION
FREE-RADICAL HYDROTHIOLATION
PHOTOINITIATED HYDROTHIOLATION
DISULFIDE
CYANIDES
EXO-GLYCALS
C-GLYCOSYLMETHYLENE CARBENES
EFFICIENT METHOD
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Summary:A series of 2-deoxy-glycopyranosyl cyanides with D-arabino, D-lyxo, D-erythro, and D-threo configurations was synthesized from the corresponding glycals via 2-deoxy-glycopyranosyl acetates. The cyanides were transformed to anhydro-aldose tosylhydrazones by reduction with NaH2PO2/Ra-Ni in the presence of tosylhydrazine. The tosylhydrazones furnished 2-deoxy-exo-glycals under modified Bamford-Stevens conditions. Photoinitiated thiol-ene additions of these exo-glycals resulted in the corresponding C-(2-deoxy-Dglycopyranosyl) methyl sulfides in medium to good yields with exclusive regio-and stereoselectivities in most cases. Several disaccharide mimics with a C-S moiety in place of the glycosidic oxygen were also obtained.
ISSN:1144-0546
1369-9261
DOI:10.1039/c8nj06138f