The stereo-and regioselective elaboration of a bromohydrin from an olefinic precursor and Pummerer ene reaction for carbon carbon bond formation are the key steps in a novel and flexible synthesis of xylo-phytosphingosine and threo-sphingosine.
A tethered aminohydroxylation route to l-arabino-[2R,3S,4R] and l-xylo-[2R,3S,4S]-C18-phytosphingosines
โ Scribed by Abhishek Dubey; Pradeep Kumar
- Book ID
- 108285451
- Publisher
- Elsevier Science
- Year
- 2009
- Tongue
- French
- Weight
- 236 KB
- Volume
- 50
- Category
- Article
- ISSN
- 0040-4039
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๐ SIMILAR VOLUMES
The first diastereoselective synthesis of L-xylo -(2R,3S,4S)-C 18 -phytosphingosine (1) has been achieved by double stereodifferentiation of enantiomerically enriched terminal olefin 14 using (DHQD) 2 -PHAL ligand in an asymmetric dihydroxylation with a diastereomeric ratio of 83:17. This phytosphin
Epoxy ring opening of 2 and 2 with [ l -1 4 C ] hexadecyl copper lo gave respectivezy t h e analog 4 of agaric acid trimethyl e s t e r and methy2 b -1 4 ~J a g a r i c a t e 5, which-was hydrolysed t o -& by Zithium hy-&oxide i n I, 2-dimethoxyethane (DME). Epoxy ring trans opening of -2 with d i