Sugar migration induced by the Wagner-Meerwein rearrangement of 28-O-glycosyl-betulin derivatives. Issue 13 (30th March 2017)
- Record Type:
- Journal Article
- Title:
- Sugar migration induced by the Wagner-Meerwein rearrangement of 28-O-glycosyl-betulin derivatives. Issue 13 (30th March 2017)
- Main Title:
- Sugar migration induced by the Wagner-Meerwein rearrangement of 28-O-glycosyl-betulin derivatives
- Authors:
- Korda, Anna
Pakulski, Zbigniew
Cmoch, Piotr
Gwardiak, Katarzyna
Karczewski, Romuald - Abstract:
- Abstract: Treatment of betulin-type saponins, in which the sugar moiety is connected at the 28-position, with TMSOTf affords 3-O-substituted allobetulin saponins. This unprecedented migration of the sugar part is driven by the Wagner-Meerwein rearrangement of the betulin core. According to our mechanistic studies an oxocarbenium ion released during the rearrangement reacts with the free 3-OH group of the triterpene affording the final allobetulin saponin. Migration rate depends on the size and configuration of the sugar moiety. Graphical abstract:
- Is Part Of:
- Tetrahedron. Volume 73:Issue 13(2017)
- Journal:
- Tetrahedron
- Issue:
- Volume 73:Issue 13(2017)
- Issue Display:
- Volume 73, Issue 13 (2017)
- Year:
- 2017
- Volume:
- 73
- Issue:
- 13
- Issue Sort Value:
- 2017-0073-0013-0000
- Page Start:
- 1740
- Page End:
- 1744
- Publication Date:
- 2017-03-30
- Subjects:
- Betulin -- Allobetulin -- Saponins -- The Wagner-Meerwein rearrangement -- Synthesis
Chemistry, Organic -- Periodicals
547.005 - Journal URLs:
- http://www.elsevier.com/journals ↗
- DOI:
- 10.1016/j.tet.2017.02.024 ↗
- Languages:
- English
- ISSNs:
- 0040-4020
- Deposit Type:
- Legaldeposit
- View Content:
- Available online (eLD content is only available in our Reading Rooms) ↗
- Physical Locations:
- British Library DSC - 8796.850000
British Library DSC - BLDSS-3PM
British Library STI - ELD Digital store - Ingest File:
- 317.xml