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Double stereodifferentiation in asymmetric dihydroxylation: application to the first diastereoselective synthesis of l-xylo-[2R,3S,4S]-C18-phytosphingosine

✍ Scribed by Rodney A Fernandes; Pradeep Kumar

Publisher: Elsevier Science
Year: 2000
Tongue: French
Weight: 76 KB
Volume: 41
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)01851-7

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✦ Synopsis

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 phytosphingosine was fully characterized by the physical and spectral data of the corresponding tetraacetate 21.

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