Synthesis and Photochemistry of a New Photolabile Protecting Group for Propargylic Alcohols

Chi Ma; Youlai Zhang; Huan Zhang; Junru Li; Yasuhiro Nishiyama; Hiroki Tanimoto; Tsumoru Morimoto; Kiyomi Kakiuchi

doi:10.1055/s-0036-1588915

Synthesis and Photochemistry of a New Photolabile Protecting Group for Propargylic Alcohols

Chi Ma, Youlai Zhang^*, Huan Zhang, Junru Li, Yasuhiro Nishiyama, Hiroki Tanimoto, Tsumoru Morimoto, Kiyomi Kakiuchi

^*この論文の責任著者

生体認識化学研究室

研究成果: ジャーナルへの寄稿 › 学術論文 › 査読

10 被引用数 (Scopus)

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A new and efficient thiochromenone S,S-dioxide-based photolabile protecting group for propargylic alcohols is described. Robust protection reactions were developed through copper (II)-catalyzed substitution of propargylic alcohols. Subsequent photodeprotection proceeded smoothly to give the corresponding propargylic alcohols quantitatively within 15 minutes, as demonstrated by ¹H NMR spectroscopy and HPLC. Notably, the photoproduct derived from the thiochromenone derivatives showed a high fluorescence quantum yield, permitting monitoring of the reaction progress by fluorescence spectroscopy. A new strategy for the synthesis of triazoles by a one-pot reaction is also presented.

本文言語	英語
論文番号	st-2016-w0578-l
ページ（範囲）	560-564
ページ数	5
ジャーナル	Synlett
巻	28
号	5
DOI	https://doi.org/10.1055/s-0036-1588915
出版ステータス	出版済み - 2017/03/15

ASJC Scopus 主題領域

有機化学

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10.1055/s-0036-1588915

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title = "Synthesis and Photochemistry of a New Photolabile Protecting Group for Propargylic Alcohols",

abstract = "A new and efficient thiochromenone S,S-dioxide-based photolabile protecting group for propargylic alcohols is described. Robust protection reactions were developed through copper (II)-catalyzed substitution of propargylic alcohols. Subsequent photodeprotection proceeded smoothly to give the corresponding propargylic alcohols quantitatively within 15 minutes, as demonstrated by 1H NMR spectroscopy and HPLC. Notably, the photoproduct derived from the thiochromenone derivatives showed a high fluorescence quantum yield, permitting monitoring of the reaction progress by fluorescence spectroscopy. A new strategy for the synthesis of triazoles by a one-pot reaction is also presented.",

keywords = "photodeprotection, photolabile groups, propargylic alcohols, protecting group, thiochromenone dioxides, triazoles",

author = "Chi Ma and Youlai Zhang and Huan Zhang and Junru Li and Yasuhiro Nishiyama and Hiroki Tanimoto and Tsumoru Morimoto and Kiyomi Kakiuchi",

note = "Publisher Copyright: {\textcopyright} Georg Thieme VerlagStuttgart · New York.",

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AU - Ma, Chi

AU - Zhang, Youlai

AU - Zhang, Huan

AU - Li, Junru

AU - Nishiyama, Yasuhiro

AU - Tanimoto, Hiroki

AU - Morimoto, Tsumoru

AU - Kakiuchi, Kiyomi

N1 - Publisher Copyright: © Georg Thieme VerlagStuttgart · New York.

PY - 2017/3/15

Y1 - 2017/3/15

N2 - A new and efficient thiochromenone S,S-dioxide-based photolabile protecting group for propargylic alcohols is described. Robust protection reactions were developed through copper (II)-catalyzed substitution of propargylic alcohols. Subsequent photodeprotection proceeded smoothly to give the corresponding propargylic alcohols quantitatively within 15 minutes, as demonstrated by 1H NMR spectroscopy and HPLC. Notably, the photoproduct derived from the thiochromenone derivatives showed a high fluorescence quantum yield, permitting monitoring of the reaction progress by fluorescence spectroscopy. A new strategy for the synthesis of triazoles by a one-pot reaction is also presented.

AB - A new and efficient thiochromenone S,S-dioxide-based photolabile protecting group for propargylic alcohols is described. Robust protection reactions were developed through copper (II)-catalyzed substitution of propargylic alcohols. Subsequent photodeprotection proceeded smoothly to give the corresponding propargylic alcohols quantitatively within 15 minutes, as demonstrated by 1H NMR spectroscopy and HPLC. Notably, the photoproduct derived from the thiochromenone derivatives showed a high fluorescence quantum yield, permitting monitoring of the reaction progress by fluorescence spectroscopy. A new strategy for the synthesis of triazoles by a one-pot reaction is also presented.

KW - photodeprotection

KW - photolabile groups

KW - propargylic alcohols

KW - protecting group

KW - thiochromenone dioxides

KW - triazoles

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U2 - 10.1055/s-0036-1588915

DO - 10.1055/s-0036-1588915

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SN - 0936-5214

VL - 28

SP - 560

EP - 564

JO - Synlett

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M1 - st-2016-w0578-l

ER -

Synthesis and Photochemistry of a New Photolabile Protecting Group for Propargylic Alcohols

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