Synthesis of halogenated-4-nitrophenyl 2-deoxy-2-halogeno-pyranosides via n-halogenosuccinimide activated glucal

Chieri Inoue; Yumi Okamoto; Christopher J. Vavricka; Hiromasa Kiyota; Minoru Izumi

doi:10.1177/1934578x1801300125

Synthesis of halogenated-4-nitrophenyl 2-deoxy-2-halogeno-pyranosides via n-halogenosuccinimide activated glucal

Chieri Inoue, Yumi Okamoto, Christopher J. Vavricka, Hiromasa Kiyota, Minoru Izumi

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

Abstract

Reaction of 3,4,6-tri-O-acetyl-D-glucal with silver 4-nitrophenolate in the presence of N-iodosuccinimide and N-bromosuccinimide produced (2,6-dihalo-4-nitro)phenyl 2-halo-2-deoxy--D-glycopyranosides. Although bromination and iodination of the 4-nitrophenyl group could not be avoided, the resulting (2,6-dihalo-4-nitro)phenylated compounds can be used as substrates or covalent glycosidase inhibitors after deprotection. The stereoselectivity and regioselectivity of the halogenation reactions are described.

Original language	English
Pages (from-to)	85-87
Number of pages	3
Journal	Natural product communications
Volume	13
Issue number	1
DOIs	https://doi.org/10.1177/1934578x1801300125
Publication status	Published - Jan 2018

Keywords

2-Deoxy sugar
2-Deoxy-2-halogeno-pyranoside
Glucal
N-Halogenosuccinimide
Silver 4-nitrophenolate

ASJC Scopus subject areas

Pharmacology
Plant Science
Drug Discovery
Complementary and alternative medicine

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10.1177/1934578x1801300125

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title = "Synthesis of halogenated-4-nitrophenyl 2-deoxy-2-halogeno-pyranosides via n-halogenosuccinimide activated glucal",

abstract = "Reaction of 3,4,6-tri-O-acetyl-D-glucal with silver 4-nitrophenolate in the presence of N-iodosuccinimide and N-bromosuccinimide produced (2,6-dihalo-4-nitro)phenyl 2-halo-2-deoxy--D-glycopyranosides. Although bromination and iodination of the 4-nitrophenyl group could not be avoided, the resulting (2,6-dihalo-4-nitro)phenylated compounds can be used as substrates or covalent glycosidase inhibitors after deprotection. The stereoselectivity and regioselectivity of the halogenation reactions are described.",

keywords = "2-Deoxy sugar, 2-Deoxy-2-halogeno-pyranoside, Glucal, N-Halogenosuccinimide, Silver 4-nitrophenolate",

author = "Chieri Inoue and Yumi Okamoto and Vavricka, {Christopher J.} and Hiromasa Kiyota and Minoru Izumi",

note = "Funding Information: Acknowledgments - The authors are grateful to Dr. Kei Matsumoto at the Division of Instrumental Analysis, Okayama University for the NMR spectral measurements. The authors are also grateful to Ms. Megumi Kosaka and Mr. Motonari Kobayashi at the Division of Instrumental Analysis, Okayama University for the measurements of elemental analyses. Financial support from KAKENHI (No. 17K07772) and Wesco Scientific Promotion Foundation are acknowledged. Publisher Copyright: {\textcopyright} 2018 Natural Product Incorporation. All Rights Reserved.",

year = "2018",

month = jan,

doi = "10.1177/1934578x1801300125",

language = "English",

volume = "13",

pages = "85--87",

journal = "Natural Product Communications",

issn = "1934-578X",

publisher = "Natural Product Communications",

number = "1",

}

TY - JOUR

T1 - Synthesis of halogenated-4-nitrophenyl 2-deoxy-2-halogeno-pyranosides via n-halogenosuccinimide activated glucal

AU - Inoue, Chieri

AU - Okamoto, Yumi

AU - Vavricka, Christopher J.

AU - Kiyota, Hiromasa

AU - Izumi, Minoru

N1 - Funding Information: Acknowledgments - The authors are grateful to Dr. Kei Matsumoto at the Division of Instrumental Analysis, Okayama University for the NMR spectral measurements. The authors are also grateful to Ms. Megumi Kosaka and Mr. Motonari Kobayashi at the Division of Instrumental Analysis, Okayama University for the measurements of elemental analyses. Financial support from KAKENHI (No. 17K07772) and Wesco Scientific Promotion Foundation are acknowledged. Publisher Copyright: © 2018 Natural Product Incorporation. All Rights Reserved.

PY - 2018/1

Y1 - 2018/1

N2 - Reaction of 3,4,6-tri-O-acetyl-D-glucal with silver 4-nitrophenolate in the presence of N-iodosuccinimide and N-bromosuccinimide produced (2,6-dihalo-4-nitro)phenyl 2-halo-2-deoxy--D-glycopyranosides. Although bromination and iodination of the 4-nitrophenyl group could not be avoided, the resulting (2,6-dihalo-4-nitro)phenylated compounds can be used as substrates or covalent glycosidase inhibitors after deprotection. The stereoselectivity and regioselectivity of the halogenation reactions are described.

AB - Reaction of 3,4,6-tri-O-acetyl-D-glucal with silver 4-nitrophenolate in the presence of N-iodosuccinimide and N-bromosuccinimide produced (2,6-dihalo-4-nitro)phenyl 2-halo-2-deoxy--D-glycopyranosides. Although bromination and iodination of the 4-nitrophenyl group could not be avoided, the resulting (2,6-dihalo-4-nitro)phenylated compounds can be used as substrates or covalent glycosidase inhibitors after deprotection. The stereoselectivity and regioselectivity of the halogenation reactions are described.

KW - 2-Deoxy sugar

KW - 2-Deoxy-2-halogeno-pyranoside

KW - Glucal

KW - N-Halogenosuccinimide

KW - Silver 4-nitrophenolate

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DO - 10.1177/1934578x1801300125

M3 - Article

AN - SCOPUS:85048512846

SN - 1934-578X

VL - 13

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JO - Natural Product Communications

JF - Natural Product Communications

IS - 1

ER -

Synthesis of halogenated-4-nitrophenyl 2-deoxy-2-halogeno-pyranosides via n-halogenosuccinimide activated glucal

Abstract

Keywords

ASJC Scopus subject areas

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