Synthesis of cyclic sphingosine 1,3-phosphate (cSPP) through a photolytic reaction

Lixin Qiao; Alan P. Kozikowski

doi:10.1016/S0040-4039(98)02071-1

Synthesis of cyclic sphingosine 1,3-phosphate (cSPP) through a photolytic reaction

Lixin Qiao
, Alan P. Kozikowski

Research output: Contribution to journal › Article › peer-review

2 Scopus citations

Abstract

The synthesis of cyclic sphingosine 1,3-phosphate through photolytic methodology is described starting from D-erythro-sphingosine. A bifunctional phosphorylating reagent, 2-cyanoethyl N,N-diisopropylchlorophosphoramidite, is used to introduce the cyclic 1,3-phosphate moiety. This procedure generates cSPP in four steps and in 36% overall yield.

Original language	English (US)
Pages (from-to)	8959-8962
Number of pages	4
Journal	Tetrahedron Letters
Volume	39
Issue number	49
DOIs	https://doi.org/10.1016/S0040-4039(98)02071-1
State	Published - Dec 3 1998
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(98)02071-1

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@article{8f1e820925cc41beba64526365727ef8,

title = "Synthesis of cyclic sphingosine 1,3-phosphate (cSPP) through a photolytic reaction",

abstract = "The synthesis of cyclic sphingosine 1,3-phosphate through photolytic methodology is described starting from D-erythro-sphingosine. A bifunctional phosphorylating reagent, 2-cyanoethyl N,N-diisopropylchlorophosphoramidite, is used to introduce the cyclic 1,3-phosphate moiety. This procedure generates cSPP in four steps and in 36\% overall yield.",

author = "Lixin Qiao and Kozikowski, \{Alan P.\}",

note = "Funding Information: Acknowledgment. We are indebted to the Department of Defense Research Grant (DAMD17-93-V-3018) for its support of this research. We wish to thank Fidia Pharmaceuticals of Abano Terme, Italy for a generous gift of D-erythro-sphingosine sulfate. The FAB-HRMS mass spectrum was recorded at the Michigan State University Mass Spectrometry Facility which is supported, in part, by a grant (DRR-00480) from the Biotechnology Research Technology Program, National Center for Research Resources, National Institutes of Health.",

year = "1998",

month = dec,

day = "3",

doi = "10.1016/S0040-4039(98)02071-1",

language = "English (US)",

volume = "39",

pages = "8959--8962",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd",

number = "49",

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TY - JOUR

T1 - Synthesis of cyclic sphingosine 1,3-phosphate (cSPP) through a photolytic reaction

AU - Qiao, Lixin

AU - Kozikowski, Alan P.

N1 - Funding Information: Acknowledgment. We are indebted to the Department of Defense Research Grant (DAMD17-93-V-3018) for its support of this research. We wish to thank Fidia Pharmaceuticals of Abano Terme, Italy for a generous gift of D-erythro-sphingosine sulfate. The FAB-HRMS mass spectrum was recorded at the Michigan State University Mass Spectrometry Facility which is supported, in part, by a grant (DRR-00480) from the Biotechnology Research Technology Program, National Center for Research Resources, National Institutes of Health.

PY - 1998/12/3

Y1 - 1998/12/3

N2 - The synthesis of cyclic sphingosine 1,3-phosphate through photolytic methodology is described starting from D-erythro-sphingosine. A bifunctional phosphorylating reagent, 2-cyanoethyl N,N-diisopropylchlorophosphoramidite, is used to introduce the cyclic 1,3-phosphate moiety. This procedure generates cSPP in four steps and in 36% overall yield.

AB - The synthesis of cyclic sphingosine 1,3-phosphate through photolytic methodology is described starting from D-erythro-sphingosine. A bifunctional phosphorylating reagent, 2-cyanoethyl N,N-diisopropylchlorophosphoramidite, is used to introduce the cyclic 1,3-phosphate moiety. This procedure generates cSPP in four steps and in 36% overall yield.

UR - https://www.scopus.com/pages/publications/0032480932

UR - https://www.scopus.com/pages/publications/0032480932#tab=citedBy

U2 - 10.1016/S0040-4039(98)02071-1

DO - 10.1016/S0040-4039(98)02071-1

M3 - Article

AN - SCOPUS:0032480932

SN - 0040-4039

VL - 39

SP - 8959

EP - 8962

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 49

ER -

Synthesis of cyclic sphingosine 1,3-phosphate (cSPP) through a photolytic reaction

Abstract

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