Stereocontrolled Synthesis of Nucleosides Based on Intramolecular Glycosylation Strategy.
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- Sugimura Hideyuki
- Faculty of Education and Human Science, Yokohama National University
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- Sujino Keiko
- Raylo Chemicals Inc.
Bibliographic Information
- Other Title
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- 分子内グリコシル化反応を基盤とするヌクレオシド類の立体選択的な合成
- ブンシ ナイ グリコシルカ ハンノウ オ キバン ト スル ヌクレオシドルイ ノ リッタイ センタクテキ ナ ゴウセイ
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Abstract
A convenient method for the stereocontrolled synthesis of nucleosides has been developed utilizing intramolecular aglycon delivery system. An important feature is to use 1-thioglycosides as glycosyl donor substrates, which can be counted as stable glycosides during modification steps of the carbohydrate moieties as well as introduction step of the pyrimidine base, but, on the other hand, the 1-thioglycosides can work as powerful glycosyl donors when they are treated with an appropriate thiophilic reagent. The suitable activator was found to be Me2S(SMe)BF4. The synthetic applicability is demonstrated by the syntheses of pharmaceutically important deoxynucleosides exemplified as ddC, AZT, FLT, some base-modified nucleosides, isonucleosides, nucleoside antibiotics, and 4'-thionucleosides.
Journal
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- Journal of Synthetic Organic Chemistry, Japan
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Journal of Synthetic Organic Chemistry, Japan 59 (9), 879-891, 2001
The Society of Synthetic Organic Chemistry, Japan
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Keywords
Details 詳細情報について
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- CRID
- 1390282680254187776
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- NII Article ID
- 10012287248
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- NII Book ID
- AN0024521X
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- ISSN
- 18836526
- 00379980
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- NDL BIB ID
- 5905538
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- Text Lang
- ja
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- Data Source
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- JaLC
- NDL
- Crossref
- CiNii Articles
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- Abstract License Flag
- Disallowed