Synthesis and Biological Evaluation of 1‐Deoxy‐5‐hydroxysphingosine Derivatives | Zendy

Esteve Judit | Zendy; Lorente Adriana | Zendy; Romea Pedro | Zendy; Urpí Fèlix | Zendy; RíosLuci Carla | Zendy; Padrón José M. | Zendy

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Synthesis and Biological Evaluation of 1‐Deoxy‐5‐hydroxysphingosine Derivatives

Author(s) -

Esteve Judit,

Lorente Adriana,

Romea Pedro,

Urpí Fèlix,

RíosLuci Carla,

Padrón José M.

Publication year - 2011

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.201001268

Subject(s) - enantiopure drug , chemistry , diastereomer , aldol reaction , ketone , diol , stereochemistry , transformation (genetics) , combinatorial chemistry , organic chemistry , enantioselective synthesis , catalysis , biochemistry , gene

A sequential transformation based on the titanium‐mediated aldol addition of ( S )‐1‐bromo‐3‐( tert ‐butyldimethylsilyloxy)‐2‐butanone, a chiral lactate‐derived ketone, to tetradecanal followed by reduction of the ensuing aldolate afforded the corresponding syn ‐1,3‐diol as a single diastereomer. Debromination and further manipulation of this intermediate allowed the efficient synthesis of two enantiopure 1‐deoxy‐5‐hydroxysphingosines, which exhibit promising biological activity against a representative panel of human cancer lines.

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