Sökning: onr:"swepub:oai:DiVA.org:su-127344" >
Synthesis of the te...
-
Angles d'Ortoli, ThibaultStockholms universitet,Institutionen för organisk kemi
(författare)
Synthesis of the tetrasaccharide glycoside moiety of Solaradixine and rapid NMR-based structure verification using the program CASPER
- Artikel/kapitelEngelska2016
Förlag, utgivningsår, omfång ...
-
Elsevier,2016
-
electronicrdacarrier
Nummerbeteckningar
-
LIBRIS-ID:oai:DiVA.org:su-127344
-
https://urn.kb.se/resolve?urn=urn:nbn:se:su:diva-127344URI
-
https://doi.org/10.1016/j.tet.2015.12.042DOI
Kompletterande språkuppgifter
-
Språk:engelska
-
Sammanfattning på:engelska
Ingår i deldatabas
Klassifikation
-
Ämneskategori:ref swepub-contenttype
-
Ämneskategori:art swepub-publicationtype
Anmärkningar
-
The major glycoalkaloid in the roots of Solanum laciniatum is Solaradixine having the branched tetrasaccharide beta-D-Glcp-(1 -> 2)-beta-D-Glcp-(1 -> 3)[alpha-L-Rhap-(1 -> 2)]-beta-D-Galp linked to O3 of the steroidal alkaloid Solasodine. We herein describe the synthesis of the methyl glycoside of the tetrasaccharide using a super-armed disaccharide as a donor molecule. A 2-(naphthyl)methyl protecting group was used in the synthesis of the donor since it was tolerant to a wide range of reaction conditions. The 6-O-benzylated-hexa-O-tert-butyldimethylsilyi-protected beta-D-Glcp-(1 -> 2)-beta-D-Glcp-SEt donor, which avoided 1,6-anydro formation, was successfully glycosylated at O3 of a galactoside acceptor molecule. However, subsequent glycosylation at O2 by a rhamnosyl donor was unsuccessful and instead a suitably protected alpha-L-Rhap(1 -> 2)-beta-D-Galp-OMe disaccharide was used as the acceptor molecule together with a super-armed beta-D-Glcp-(1 -> 2)-beta-D-Glcp-SEt donor in the glycosylation reaction, to give a tetrasaccharide in a yield of 55%, which after deprotection resulted in the target molecule, the structure of which was verified by the NMR chemical shift prediction program CASPER.
Ämnesord och genrebeteckningar
Biuppslag (personer, institutioner, konferenser, titlar ...)
-
Widmalm, GöranStockholms universitet,Institutionen för organisk kemi(Swepub:su)gw
(författare)
-
Stockholms universitetInstitutionen för organisk kemi
(creator_code:org_t)
Sammanhörande titlar
-
Ingår i:Tetrahedron: Elsevier72:7, s. 912-9270040-40201464-5416
Internetlänk
Hitta via bibliotek
Till lärosätets databas