Erythro-Sphingosine

Scheme 2.32 Stereodivergent synthesis of threo- and erythro-sphingosines 124.

This method has been applied in the enantioselective synthesis of d-erythro-sphingosine and phytosphingosine. Sphingosine became an important substance for studying signal transduction since the discovery of protein kinase C inhibition by this compound.48 Many efforts have been made to synthesize sphingosine and its derivatives.49 Kobayashi et al. reported another route to this type of compound in which a Lewis acid-catalyzed asymmetric aldol reaction was a key step. 

Pushkareva, M., Chao, R., Bielawska, A., Merrill Jr, A.H., Crane, H.M., Lagu, B., liotta, D. and Hannun, Y.A., 1995, Stereoselectivity of induction of the retinoblastoma gene product (pRb) dephosphorylation by D-erythro-sphingosine supports a role for pRb in growth suppression by sphingosine, Biochem. 34 1885-1892. 

A novel regioselective, convenient and efficient synthesis of model D-erythro-sphingosine 1-phosphate (87) and D-erythro-ceramide 1-phosphate (88) has been presented. ... 

D-erythro-sphingosine and ceramide sphingosine (89) and ceramide (90) and their phosphates (87) and (88) constitute a highly conserved, plasma-membrane derived set of molecular tools which eukaryotic cells use to trigger a variety of... 

Geramide G6 (6-Hexanoyl-d-erythro-sphingosine Fisher Scientific). 

The most prevalent membrane sphingolipid present in the outer leaflet of the cell membrane is sphingomyelin. Sphingomyelin consists of a D-erythro-sphingosine connected via an amide ester bond with a fatty acid containing... 

Ring opening of epoxides is an effective route to amino-alcohols. The epoxide (27) was transformed, via an oxazolidinone route, into D-erythro-sphingosine (28) (Scheme 56). 

Wannaporn, D. and Ishikawa, T. (2005) Chirality transfer from guanidinium ylides to 3-alkenyl (or 3-alkynyl) aziridine-2-carboxylates and application to the syntheses of (2/J,35)-3-hydro-xyleucinate and D-erythro-sphingosine. The Journal of Organic Chemistry, 70, 9399-9406. 

This year has again seen several synthetic routes to sphingosines and analogues. Oxazolidinone 312 was converted by the same workers to o-erythro-sphingosine 319 in six steps and JV-benzoyl glucosamine has also been elabo-... 

Scheme 13.19 Identifying vinylglycine as possible precursor for polyoxamic acid 4.2 D-Erythro-Sphingosine...

Scheme 13.20 Identifying precursor molecules for D-erythro-sphingosine from the chiral pool...

The substitution pattern of D-erythro-sphingosine (Scheme 4.10) could also arise from an epoxy-alcohol. This suggests the Sharpless epoxidation as a suitable inroute [15] (Scheme 13.21). 

Scheme 13.21 Asymmetric synthesis route to D-erythro-sphingosine...

Utilized to obtain the adduct with anti configuration hydrolysis of this has led to D-erythro-sphingosine (91T2835). 

Four sphingosines were analyzed as their V-naphthimide derivatives on a silica column (A = 260 run, ex 370 nm, em) using a 35/25/20 hexane/chloroform/ethyl acetate mobile phase [781], The threo-, 2H-threo-, 2H-erythm-, and erythro-sphingosines were baseline resolved in 23 min. Picomole detection limits were claimed. 

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