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- 鳥飼 浩平
- 九州大学大学院理学研究院化学部門
書誌事項
- タイトル別名
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- Development and Application of Novel Alkoxymethyl Groups
- シンキ アルコキシメチルキ ノ カイハツ ト ソノ オウヨウ
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<p>Protecting groups (PGs) still occupy an important position in the organic synthesis, despite negative campaign declaring that the use of them is not step-economical. Although an enormous number of PGs have been developed to date, there still are demands of new PGs that can be installed and cleaved at the desired timing and situation. Recently, we have focused on some projects to revisit the usefulness of alkoxymethyl PGs. In this review article, the property of 2-naphthylmethoxymethyl (NAPOM or NOM) and 1-naphthylmethoxymethyl (1-NAPOM, NAPOMI or NOMI) groups, our newly developed alkoxymethyl PGs, would first be introduced. Subsequently, application of the alkoxymethyl PGs to peptide- and glyco-chemistry was discussed. In the peptide chemistry, the NAPOM group was introduced on a π-nitrogen of histidine to suppress the racemization during peptide synthesis. On the other hand, in the glycochemistry, alkoxymethyl PGs were installed on a hydroxy group at C2 position, and used for the anchimeric assistance to ensure 1,2-trans selective glycosylation. Furthermore, because 2-O-alkoxymethyl protected donors were found to be more reactive than the conventional 2-O-acyl ones, a one-pot strategy for the synthesis of 1,2-trans oligosaccharides could be developed.</p>
収録刊行物
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- 有機合成化学協会誌
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有機合成化学協会誌 79 (3), 210-223, 2021-03-01
公益社団法人 有機合成化学協会
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詳細情報 詳細情報について
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- CRID
- 1390568772519649664
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- NII論文ID
- 130007996109
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- NII書誌ID
- AN0024521X
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- ISSN
- 18836526
- 00379980
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- NDL書誌ID
- 031339475
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- 本文言語コード
- ja
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- データソース種別
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- JaLC
- NDL
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