Synthesis of α-N-Glycosides of 3-Deoxy-D-g/ym0-D-ga/act0-2-nonulosonic Acid (KDN) Using Nucleobases and Their Photocycloaddition to 2,3-Dimethyl-2-butene

Xue Sun; Naoki Haga; Hiroaki Takayanagi; Haruo Ogura

doi:10.1248/cpb.42.2352

Synthesis of α-N-Glycosides of 3-Deoxy-D-g/ym0-D-ga/act0-2-nonulosonic Acid (KDN) Using Nucleobases and Their Photocycloaddition to 2,3-Dimethyl-2-butene

Xue Sun
, Naoki Haga
, Hiroaki Takayanagi
, Haruo Ogura

Chemistry

Kitasato University
Sialic Acids Society

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

9 Scopus citations

Abstract

α-N-Glycosides of 3-deoxy-D-glycero-D-galacto-2-nonulosonic acid (KDN) having a nucleobase, such as uracil, thymine, 5-fluorouracil or cytosine, were synthesized. Their acetone-sensitized photocycloaddition to 2,3-dimethyl-2-butene under near-UV irradiation gave a pair of diastereomers having a cyclobutane ring. The absolute configuration of the bridgehead carbon atoms in the products was identified by measurement of specific rotation as well as 1H-NMR spectral analysis. © 1994, The Pharmaceutical Society of Japan. All rights reserved.

Original language	English
Pages (from-to)	2352-2356
Number of pages	5
Journal	Chemical and Pharmaceutical Bulletin
Volume	42
Issue number	11
DOIs	https://doi.org/10.1248/cpb.42.2352
State	Published - Jan 1 1994

Keywords

2,3-dimethyl-2-butene
3-deoxy-D-glycero-D-galacto-2-nonulosonic acid (KDN)
N-glycosides
photocycloaddition
pyrimidine base

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10.1248/cpb.42.2352

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title = "Synthesis of α-N-Glycosides of 3-Deoxy-D-g/ym0-D-ga/act0-2-nonulosonic Acid (KDN) Using Nucleobases and Their Photocycloaddition to 2,3-Dimethyl-2-butene",

abstract = "α-N-Glycosides of 3-deoxy-D-glycero-D-galacto-2-nonulosonic acid (KDN) having a nucleobase, such as uracil, thymine, 5-fluorouracil or cytosine, were synthesized. Their acetone-sensitized photocycloaddition to 2,3-dimethyl-2-butene under near-UV irradiation gave a pair of diastereomers having a cyclobutane ring. The absolute configuration of the bridgehead carbon atoms in the products was identified by measurement of specific rotation as well as 1H-NMR spectral analysis. {\textcopyright} 1994, The Pharmaceutical Society of Japan. All rights reserved.",

keywords = "2,3-dimethyl-2-butene, 3-deoxy-D-glycero-D-galacto-2-nonulosonic acid (KDN), N-glycosides, photocycloaddition, pyrimidine base",

author = "Xue Sun and Naoki Haga and Hiroaki Takayanagi and Haruo Ogura",

year = "1994",

month = jan,

day = "1",

doi = "10.1248/cpb.42.2352",

language = "English",

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T1 - Synthesis of α-N-Glycosides of 3-Deoxy-D-g/ym0-D-ga/act0-2-nonulosonic Acid (KDN) Using Nucleobases and Their Photocycloaddition to 2,3-Dimethyl-2-butene

AU - Sun, Xue

AU - Haga, Naoki

AU - Takayanagi, Hiroaki

AU - Ogura, Haruo

PY - 1994/1/1

Y1 - 1994/1/1

N2 - α-N-Glycosides of 3-deoxy-D-glycero-D-galacto-2-nonulosonic acid (KDN) having a nucleobase, such as uracil, thymine, 5-fluorouracil or cytosine, were synthesized. Their acetone-sensitized photocycloaddition to 2,3-dimethyl-2-butene under near-UV irradiation gave a pair of diastereomers having a cyclobutane ring. The absolute configuration of the bridgehead carbon atoms in the products was identified by measurement of specific rotation as well as 1H-NMR spectral analysis. © 1994, The Pharmaceutical Society of Japan. All rights reserved.

AB - α-N-Glycosides of 3-deoxy-D-glycero-D-galacto-2-nonulosonic acid (KDN) having a nucleobase, such as uracil, thymine, 5-fluorouracil or cytosine, were synthesized. Their acetone-sensitized photocycloaddition to 2,3-dimethyl-2-butene under near-UV irradiation gave a pair of diastereomers having a cyclobutane ring. The absolute configuration of the bridgehead carbon atoms in the products was identified by measurement of specific rotation as well as 1H-NMR spectral analysis. © 1994, The Pharmaceutical Society of Japan. All rights reserved.

KW - 2,3-dimethyl-2-butene

KW - 3-deoxy-D-glycero-D-galacto-2-nonulosonic acid (KDN)

KW - N-glycosides

KW - photocycloaddition

KW - pyrimidine base

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U2 - 10.1248/cpb.42.2352

DO - 10.1248/cpb.42.2352

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JO - Chemical and Pharmaceutical Bulletin

JF - Chemical and Pharmaceutical Bulletin

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ER -

Synthesis of α-N-Glycosides of 3-Deoxy-D-g/ym0-D-ga/act0-2-nonulosonic Acid (KDN) Using Nucleobases and Their Photocycloaddition to 2,3-Dimethyl-2-butene

Abstract

Keywords

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