309919-03-7Relevant articles and documents
Practical syntheses of sphingosine-1-phosphate and analogues
Blot, Virginie,Jacquemard, Ulrich,Reissig, Hans-Ulrich,Kleuser, Burkhard
experimental part, p. 759 - 766 (2009/07/19)
Sphingosine-1-phosphate (S1P, 1) is a bioactive sphin- golipid metabolite involved in a variety of critical cellular processes including proliferation, survival, and migration. For this reason the stereoselective syntheses of S1P and analogues are of great interest. Based on L-serine as source of chirality we achieved practical routes to prepare S1P (1) and the aryl group containing analogues 3 and 4 in fair amounts. The crucial stages of the syntheses are: introduction of the required side chain by addition of appropriate organometal- lics to Garner's aldehyde and conversion of the primary alcohols into the corresponding phosphates. Georg Thieme Verlag Stuttgart.
Synthesis of Ceramide Analogues Having the C(4)-C(5) Bond of the Long-Chain Base as Part of an Aromatic or Heteroaromatic System
Chun, Jiong,He, Linli,Byun, Hoe-Sup,Bittman, Robert
, p. 7634 - 7640 (2007/10/03)
Two efficient and stereoselective methods are described for the preparation of aryl and heteroaryl ceramide analogues 2 and 3. The first route involves the addition of an aryllithium or a heteroaryllithium reagent (7a or 25a, respectively) to the L-serine-derived aldehyde 4, followed by hydrolysis of the oxazolidine, liberation of the amino group, and N-acylation. The second route, which was used to prepare arylceramide analogue 2 in eight steps and 28% overall yield starting with 3-bromobenzaldehyde, utilizes a Heck reaction to afford (E)-α,β-unsaturated ester 16, then osmium-catalyzed asymmetric dihydroxylation for the introduction of the desired chirality at C-2 and C-3. Regioselective α-azidation of α-O-nosyl-β-hydroxyester 18 with sodium azide, followed by LiAlH4 reduction of the azido and ester groups and N-acylation, complete the synthesis of arylceramide analogue 2.
