Concise synthesis of 23-hydroxylated vitamin D                         3                          metabolites

Fumihiro Kawagoe; Toru Sugiyama; Kaori Yasuda; Motonari Uesugi; Toshiyuki Sakaki; Atsushi Kittaka

doi:10.1016/j.jsbmb.2018.10.010

Concise synthesis of 23-hydroxylated vitamin D ₃ metabolites

Fumihiro Kawagoe, Toru Sugiyama, Kaori Yasuda, Motonari Uesugi, Toshiyuki Sakaki, Atsushi Kittaka

Faculty of Pharmaceutical Sciences

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

11 Scopus citations

Abstract

Three 23-hydroxylated vitamin D ₃ derivatives, which are metabolites of 25-hydroxyvitamin D ₃ produced by CYP24A1 and a related diastereomer, were efficiently synthesized. Each C23 hydroxy unit was constructed by the Claisen condensation reaction with ethyl acetate or the Grignard reaction with 2-methylallymagnesium chloride. Stereochemistry at the C23 position was determined by a modified Mosher's method. The triene structures were constructed by the Wittig-Horner reaction utilizing the A-ring phosphine oxide moiety.

Original language	English
Pages (from-to)	161-168
Number of pages	8
Journal	Journal of Steroid Biochemistry and Molecular Biology
Volume	186
DOIs	https://doi.org/10.1016/j.jsbmb.2018.10.010
State	Published - Feb 2019

Keywords

23-Hydroxyvitamin D
Modified Mosher's method
Synthesis
Vitamin D metabolite

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10.1016/j.jsbmb.2018.10.010

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title = " Concise synthesis of 23-hydroxylated vitamin D 3 metabolites ",

abstract = " Three 23-hydroxylated vitamin D 3 derivatives, which are metabolites of 25-hydroxyvitamin D 3 produced by CYP24A1 and a related diastereomer, were efficiently synthesized. Each C23 hydroxy unit was constructed by the Claisen condensation reaction with ethyl acetate or the Grignard reaction with 2-methylallymagnesium chloride. Stereochemistry at the C23 position was determined by a modified Mosher's method. The triene structures were constructed by the Wittig-Horner reaction utilizing the A-ring phosphine oxide moiety.",

keywords = "23-Hydroxyvitamin D, Modified Mosher's method, Synthesis, Vitamin D metabolite",

author = "Fumihiro Kawagoe and Toru Sugiyama and Kaori Yasuda and Motonari Uesugi and Toshiyuki Sakaki and Atsushi Kittaka",

note = "Publisher Copyright: {\textcopyright} 2018 Elsevier Ltd",

year = "2019",

month = feb,

doi = "10.1016/j.jsbmb.2018.10.010",

language = "英語",

volume = "186",

pages = "161--168",

journal = "Journal of Steroid Biochemistry and Molecular Biology",

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}

Concise synthesis of 23-hydroxylated vitamin D ₃ metabolites . / Kawagoe, Fumihiro; Sugiyama, Toru; Yasuda, Kaori et al.
In: Journal of Steroid Biochemistry and Molecular Biology, Vol. 186, 02.2019, p. 161-168.

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

TY - JOUR

T1 - Concise synthesis of 23-hydroxylated vitamin D 3 metabolites

AU - Kawagoe, Fumihiro

AU - Sugiyama, Toru

AU - Yasuda, Kaori

AU - Uesugi, Motonari

AU - Sakaki, Toshiyuki

AU - Kittaka, Atsushi

PY - 2019/2

Y1 - 2019/2

N2 - Three 23-hydroxylated vitamin D 3 derivatives, which are metabolites of 25-hydroxyvitamin D 3 produced by CYP24A1 and a related diastereomer, were efficiently synthesized. Each C23 hydroxy unit was constructed by the Claisen condensation reaction with ethyl acetate or the Grignard reaction with 2-methylallymagnesium chloride. Stereochemistry at the C23 position was determined by a modified Mosher's method. The triene structures were constructed by the Wittig-Horner reaction utilizing the A-ring phosphine oxide moiety.

AB - Three 23-hydroxylated vitamin D 3 derivatives, which are metabolites of 25-hydroxyvitamin D 3 produced by CYP24A1 and a related diastereomer, were efficiently synthesized. Each C23 hydroxy unit was constructed by the Claisen condensation reaction with ethyl acetate or the Grignard reaction with 2-methylallymagnesium chloride. Stereochemistry at the C23 position was determined by a modified Mosher's method. The triene structures were constructed by the Wittig-Horner reaction utilizing the A-ring phosphine oxide moiety.

KW - 23-Hydroxyvitamin D

KW - Modified Mosher's method

KW - Synthesis

KW - Vitamin D metabolite

UR - http://www.scopus.com/inward/record.url?scp=85056355382&partnerID=8YFLogxK

U2 - 10.1016/j.jsbmb.2018.10.010

DO - 10.1016/j.jsbmb.2018.10.010

M3 - 記事

C2 - 30367940

AN - SCOPUS:85056355382

SN - 0960-0760

VL - 186

SP - 161

EP - 168

JO - Journal of Steroid Biochemistry and Molecular Biology

JF - Journal of Steroid Biochemistry and Molecular Biology

ER -

Concise synthesis of 23-hydroxylated vitamin D ₃ metabolites

Abstract

Keywords

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