Efficient synthesis of D-erythro-sphingosine and D-erythro-azidosphingosine from D-ribo-phytosphingosine via a cyclic sulfate intermediate.
The synthesis of naturally occurring d-erythro-sphingosine and synthetically useful D-erythro-2-azidosphingosine from commercially available d-ribo-phytosphingosine is described. An important feature of this synthesis is the selective transformation of the 3,4-vicinal diol of phytosphingosine into the characteristic E-allylic alcohol of sphingosine via a cyclic sulfate intermediate.
Kim
Sanghee
S
College of Pharmacy, Seoul National University, San 56-1, Shilim, Kwanak, Seoul 151-742, Korea. pennkim@snu.ac.kr
Lee
Sukjin
S
Lee
Taeho
T
Ko
Hyojin
H
Kim
Deukjoon
D
D003500:Cyclization; D015394:Molecular Structure; D013110:Sphingosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D013431:Sulfates / Q000737:chemistry*
C521789:D-erythro-azidosphingosine; C521790:D-ribo-phytosphingosine; D013431:Sulfates; D013110:Sphingosine