884848-75-3Relevant academic research and scientific papers
A general, efficient and stereospecific route to sphingosine, sphinganines, phytosphingosines and their analogs
Cai, Ye,Ling, Chang-Chun,Bundle, David R.
, p. 1140 - 1146 (2006)
Sphingosine, sphinganines and phytosphingosines and their analogs were synthesized by an aldol condensation between an iminoglycinate bearing a (+)-(1R,2R,5R)-2-hydroxy-3-pinanone group as chiral auxiliary and an appropriate aldehyde. All condensations proceeded with excellent enantioselectivity to generate the (2S,3R)-d-erythro structures in good yields. The Royal Society of Chemistry 2006.
Stereoselective total synthesis of passifloricin A
Reddy, Cheruku Ravindra,Veeranjaneyulu, Boyapati,Nagendra, Siddavatam,Das, Biswanath
, p. 505 - 513 (2013)
The stereoselective total synthesis of passifloricin A (1), a naturally occurring dihydropyranone with leishmanicidal and antiprotozoal activities, has been accomplished starting from protected glyceraldehyde using Maruoka asymmetric allylation, diastereoselective iodo-carbonate cyclization, and Grubbs' olefin metathesis reactions as the key steps. Copyright
A Stereocontrolled, Efficient Synthetic Route to Bioactive Sphingolipids: Synthesis of Phytosphingosine and Phytoceramides from Unsaturated Ester Precursors via Cyclic Sulfate Intermediates
He, Linli,Byun, Hoe-Sup,Bittman, Robert
, p. 7618 - 7626 (2007/10/03)
An efficient and highly enantioselective method for the preparation of D-ribo- and L-lyxo-phytosphingosines (1a,b, respectively) and phytoceramides (2a,b) has been developed. The key steps in the syntheses are as follows: (i) osmium-catalyzed asymmetric dihydroxylation of 4-O-protected (E)-α,β-unsaturated ester 5 (generated by dihydroxylation of 1-hexadecene, followed by oxidation to the aldehyde and Horner-Wadsworth-Emmons olefination), (ii) conversion to cyclic sulfate intermediate 7, and (iii) regioselective α-azidation of 7. Reduction of 4-O-protected 2-azido ester 8 via α-azidolactone 9 afforded phytosphingosine 1a. Staudinger reduction of the azido group of 8, followed by in situ N-acylation in aqueous media and reduction of the ester functionality with NaBH4/LiBr, provided phytoceramide 2a. By using a similar approach, phytosphingosine 1b was synthesized. D-erythro-4,5-Dihydrosphingosine 1c and D-erythro-4,5-dihydroceramide 2c were synthesized in high yield from 1-hexadecanol via cyclic sulfate intermediate 15. The desired configurations at C-2, C-3, and C-4 of the sphingoid chain can be accessed readily by the route described here.
