- An efficient synthesis of sphingosine-1-phosphate
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The total synthesis of D-erythro-sphingosine-1-phosphate (2) via the phosphoramidite approach, starting from 3-O-TBDMS-protected D-erythro-azidosphingosine 3 is described.
- Kratzer, Bernd,Schmidt, Richard R.
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- Synthesis of D-erythro-sphingomyelin and of D-erythro-ceramide-1-phosphoinositol
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3-O-Silyl-protected azidosphingosine 3, readily available from D-erythro-azidosphingosine, is transformed into ceramidyl phosphite derivative 5 which is a versatile building block for the synthesis of ceramide-1-O-phosphate and derivatives. This is exhibited for the synthesis of the title compounds 1 and 2.
- Kratzer, Bernd,Mayer, Thomas G.,Schmidt, Richard R.
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p. 6881 - 6884
(2007/10/02)
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- An efficient route to N palmitoyl D crythro sphingomyelin and its 13C-labeled derivatives
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We describe here a practical and efficient route to a homogeneous N palmitoyl D crythro sphingomyelin and its 13C-labeled derivatives. (2S, 3R,4E)-2-Azido-3-(tert-butyldimethylsilyloxy)-4-octadecene-l-ol1 was converted to the sphingosine equivalent 2 by treatment with triphenylphosphine and water. Amine 2 was then coupled with palmitic acid, affording the ceramide derivative 3a. In the following two reactions the phosphorylcholine functional group was generated by using 2-chloro-2-oxo-1,3,2-dioxaphospholane and trimethylamine, respectively. The final deprotection of the secondary hydroxyl group in 5a produced the desired N palmitoyl D crythro sphingomyelin 6a. The overall yield of this five-step synthesis is 43%. The melting point, 213-215°C, the specific rotation, [α]20D - +6.8 (c= 1-3, CH2Cl2MeOH 1:1) and 1H-and 13C-NMR data indicate that the synthetic sphingomyelin is enantiomerically pure. The 13C-labeled derivatives 6b, 6c and 6d were synthesized by employing the same scheme.
- Dong, Zhengxin,Butcher Jr., Jared A.
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- A useful synthesis of D-erythro-sphingomyelins
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A practical and efficient synthesis of N-palmitoyl-D-erythro-sphongomyelin is reported here, providing a general method for the preparation of various sphingomyelins bearing different N-acyl chains.
- Dong,Butcher Jr.
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p. 5291 - 5294
(2007/10/02)
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