Efficient and selective synthesis of D-arabino-, D-lyxo-, and D-xylo-phytosphingosine from D-ribo-phytosphingosine.
A new high-yield approach to the regio- and stereoselective synthesis of d-arabino-, D-lyxo-, and D-xylo-phytosphingosines from inexpensive D-ribo-phytosphingosine is described. The synthetic methodologies mainly rely on the selective configurational inversion of the stereocenter through a neighboring group participation mechanism.
Kim
Sanghee
S
College of Pharmacy, Seoul National University, San 56-1, Shilim, Kwanak, Seoul 151-742, Korea. pennkim@snu.ac.kr
Lee
Nakyong
N
Lee
Sukjin
S
Lee
Taeho
T
Lee
Yun Mi
YM
D007536:Isomerism; D009682:Magnetic Resonance Spectroscopy; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013110:Sphingosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry
C012491:phytosphingosine; D013110:Sphingosine