Sphingosine D-erythro

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. 

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). 

The enal (117) is easily obtained from tri-0-benzyl-D-galactal by mercuric-ion catalysed ring opening, and has been used to make D-erythro-sphingosine (118). Sphingosine and ceramide stereoisomers with (35)-configuration have been made from D-glucose, with the intermediacy of 2,4-O-benzylidene-D-erythrose.82... 

It was elaborated in connection with an enatioselective synthesis of D-erythro-sphingosine 132, starting from epoxide 126. There was the intention to use an intramolecular ring cleavage with an N-nucleophile to arrive at the amino-diol pattern present in sphingosine [41]. 

Brief, E., Kwak, S., Cheng,J.T.J., Kitson, N.,Thewalt,J., Lafleur, M., 2009. Phase behavior of an equimolar mixture of n-palmitoyl-d-erythro-sphingosine, cholesterol, and palmitic acid, a mixture with optimized hydrophobic matching. Langmuir 25,7523. 

Nakamura, T. and Shiozaki, M. (1999) An alternative synthesis of d-erythro-sphingosine and L-lyxo-phytosphingosine. Tetrahedron Lett., 40, 9063-9064. 

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