Enantioselective Synthesis of  D ‐ erythro ‐Sphingosine and of Ceramide | Zendy

Julina Radomir | Zendy; Herzig Thomas | Zendy; Bernet Bruno | Zendy; Vasella Andrea | Zendy

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Enantioselective Synthesis of D ‐ erythro ‐Sphingosine and of Ceramide

Author(s) -

Julina Radomir,

Herzig Thomas,

Bernet Bruno,

Vasella Andrea

Publication year - 1986

Publication title -

helvetica chimica acta

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.74

H-Index - 82

eISSN - 1522-2675

pISSN - 0018-019X

DOI - 10.1002/hlca.19860690216

Subject(s) - chemistry , sphingosine , ceramide , enantioselective synthesis , regioselectivity , diastereomer , stereochemistry , yield (engineering) , intramolecular force , organic chemistry , biochemistry , catalysis , receptor , apoptosis , materials science , metallurgy

The enynol 2 was transformed into D ‐ erythro ‐sphingosine 11 (7 steps, 46%) and into ceramide 1 (8 steps, 41% overall yield). The key steps were the mono‐epoxidation of the enynol 5 (Ti( t ‐BuO) 4 , (−)‐ D ‐diethyl tartrate, t ‐BuOOH) to 6 (86%, ≥ 98% ee), the regioselective intramolecular opening of the oxirane 6 via the benzylurethane 7 , and the reductive tranformation of the acetylene 9 into the oxazolidinone 10 (Li, EtNH 2 , 88%).

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