Enantioselective Synthesis of Homosphingosine Derivatives from L-Aspartic Acid

Sami J.K. Sauerland; Joel A. Castillo-Melendez; Kalle Nattinen; Kari Rissanen; Ari M.P. Koskinen

doi:10.1055/s-0029-1219081

Enantioselective Synthesis of Homosphingosine Derivatives from L-Aspartic Acid

Sami J.K. Sauerland, Joel A. Castillo-Melendez, Kalle Nattinen, Kari Rissanen, Ari M.P. Koskinen

Tutkimustuotos: Lehtiartikkeli › Article › Scientific › vertaisarvioitu

8 Sitaatiot (Scopus)

231 Lataukset (Pure)

Abstrakti

The sterically demanding 9-phenylfluorenyl N-protection of a number of amino acids allows the formation of amino acid derived b-ketophosphonate reagents and their Horner–Wadsworth–Emmons olefination. In an attempt to develop a synthesis of Derythro-homosphingosine in enantiopure form, we have shown that the reactivity of the intermediates is influenced by the distinctive conformational requirements of this large protecting group.

Alkuperäiskieli	Englanti
Sivut	757-762
Julkaisu	SYNTHESIS: STUTTGART
Numero	5
DOI - pysyväislinkit	https://doi.org/10.1055/s-0029-1219081
Tila	Julkaistu - 2010
OKM-julkaisutyyppi	A1 Alkuperäisartikkeli tieteellisessä aikakauslehdessä

Tutkimusalat

Synthesis

Pääsy asiakirjaan

10.1055/s-0029-1219081

ms150Accepted author manuscript, 260 KB

CCDC 255364: Experimental Crystal Structure Determination
Sauerland, S. J. K. (Creator), Castillo-Melendez, J. A. (Creator), Nättinen, K. (Creator), Rissanen, K. (Creator) & Koskinen, A. (Creator), Cambridge Crystallographic Data Centre , 25 maalisk. 2011
DOI - pysyväislinkki: 10.5517/cc8kqk2, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc8kqk2&sid=DataCite
Tietoaineisto: Dataset
CCDC 255365: Experimental Crystal Structure Determination
Karppanen, E. (Creator) & Koskinen, A. (Creator), Cambridge Crystallographic Data Centre , 25 maalisk. 2011
DOI - pysyväislinkki: 10.5517/cc8kql3, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc8kql3&sid=DataCite
Tietoaineisto: Dataset

Siteeraa tätä

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title = "Enantioselective Synthesis of Homosphingosine Derivatives from L-Aspartic Acid",

abstract = "The sterically demanding 9-phenylfluorenyl N-protection of a number of amino acids allows the formation of amino acid derived b-ketophosphonate reagents and their Horner–Wadsworth–Emmons olefination. In an attempt to develop a synthesis of Derythro-homosphingosine in enantiopure form, we have shown that the reactivity of the intermediates is influenced by the distinctive conformational requirements of this large protecting group.",

keywords = "Synthesis, Synthesis, diastereoselectivity, enantioselectivity, sphingosine, ceramide",

author = "Sauerland, {Sami J.K.} and Castillo-Melendez, {Joel A.} and Kalle Nattinen and Kari Rissanen and Koskinen, {Ari M.P.}",

year = "2010",

doi = "10.1055/s-0029-1219081",

language = "English",

pages = "757--762",

journal = "SYNTHESIS: STUTTGART",

issn = "0039-7881",

publisher = "Georg Thieme Verlag",

number = "5",

}

TY - JOUR

T1 - Enantioselective Synthesis of Homosphingosine Derivatives from L-Aspartic Acid

AU - Sauerland, Sami J.K.

AU - Castillo-Melendez, Joel A.

AU - Nattinen, Kalle

AU - Rissanen, Kari

AU - Koskinen, Ari M.P.

PY - 2010

Y1 - 2010

N2 - The sterically demanding 9-phenylfluorenyl N-protection of a number of amino acids allows the formation of amino acid derived b-ketophosphonate reagents and their Horner–Wadsworth–Emmons olefination. In an attempt to develop a synthesis of Derythro-homosphingosine in enantiopure form, we have shown that the reactivity of the intermediates is influenced by the distinctive conformational requirements of this large protecting group.

AB - The sterically demanding 9-phenylfluorenyl N-protection of a number of amino acids allows the formation of amino acid derived b-ketophosphonate reagents and their Horner–Wadsworth–Emmons olefination. In an attempt to develop a synthesis of Derythro-homosphingosine in enantiopure form, we have shown that the reactivity of the intermediates is influenced by the distinctive conformational requirements of this large protecting group.

KW - Synthesis

KW - diastereoselectivity

KW - enantioselectivity

KW - sphingosine

KW - ceramide

U2 - 10.1055/s-0029-1219081

DO - 10.1055/s-0029-1219081

M3 - Article

SN - 0039-7881

SP - 757

EP - 762

JO - SYNTHESIS: STUTTGART

JF - SYNTHESIS: STUTTGART

IS - 5

ER -

Enantioselective Synthesis of Homosphingosine Derivatives from L-Aspartic Acid

Abstrakti

Tutkimusalat

Pääsy asiakirjaan

Sormenjälki

Tietoaineistot

CCDC 255364: Experimental Crystal Structure Determination

CCDC 255365: Experimental Crystal Structure Determination

Siteeraa tätä