1176-44-9Relevant academic research and scientific papers
Complex biohopanoids synthesis: Efficient anchoring of ribosyl subunits onto a C30 hopane
Pan, Weidong,Sun, Chao,Zhang, Yongmin,Liang, Guangyi,Sinay, Pierre,Vincent, Stephane P.
, p. 1471 - 1480 (2008/02/04)
Bacteriohopanoids represent a particularly important series of triterpenoids, widely distributed in bacteria. One of the common features of these pentacyclic hopanepolyols is the presence of an extended non-terpenoid and polyhydroxylated side chain attached to the triterpenic moiety through a C-C bond. The biological function of biohopanoids also has to be addressed when one considers the broad diversity in both structures and functionalities found in the side chain. Moreover, the stereochemistries of some biohopanoids are still unconfirmed, due to the lack of synthetic methods to prepare them. In this study we describe an efficient methodology for the formation of the C-C bond between the C30-hopane component and C5-polyhydroxylated carbohydrates through the use of a hopanyllithium intermediate, which has enabled us to synthesize several biohopanoid derivatives. We also report the first synthesis of hopanepentol bearing an additional hydroxy group at position C31.
Concise syntheses of bacteriohopanetetrol and its glucosamine derivative
Pan, Weidong,Zhang, Yongmin,Liang, Guangyi,Vincent, Stephane P.,Sinay, Pierre
, p. 3445 - 3447 (2007/10/03)
This study describes the syntheses of bacteriohopanetetrol and its glucosamine derivative through a key direct coupling of a ribose derivative to the hopane skeleton. The Royal Society of Chemistry 2005.
Bromine, N-bromosuccinimide and sulphur induced isomerizations in the hopane series
Bisseret, Philippe,Rohmer, Michel
, p. 7445 - 7448 (2007/10/02)
When reacted with bromine, N-bromosuccinimide or molten sulphur, triterpenoids of the 17β(H),21β(H)-hopane series were converted into their 17α(H),21β(H) and 17β(H),21α(H) isomers of geochemical significance.
