ボロン酸触媒を活用した位置および1,2-<i>cis</i>-立体選択的グリコシル化反応の開発と応用

• 高橋 大介

  慶應義塾大学理工学部応用化学科

書誌事項

タイトル別名

• Development and Application of Boronic-Acid-Catalyzed Regioselective and 1,2-cis-Stereoselective Glycosylation
• ボロン酸触媒を活用した位置および1,2-cis-立体選択的グリコシル化反応の開発と応用
• ボロンサン ショクバイ オ カツヨウ シタ イチ オヨビ 1,2-cis-リッタイ センタクテキ グリコシルカ ハンノウ ノ カイハツ ト オウヨウ

抄録

1,2-cis-Glycosides are frequently found in many biologically active natural products and pharmaceutical compounds. Therefore, to elucidate the precise biological roles of these carbohydrates and structure-activity relationships, the development of efficient glycosylation methods for the stereoselective synthesis of 1,2-cis-glycosides is becoming increasingly important in synthetic organic chemistry. In this review article, development of boronic-acid-catalyzed regioselective and 1,2-cis-stereoselective glycosylation that was recently developed in our laboratory, is introduced. This glycosylation method was successfully applied to the regioselective and stereoselective formation of 1,2-cis-β-glycosidic linkages, to the efficient synthesis of complex glycosides, and to the direct regioselective and 1,2-cis-stereoselective glycosylation of unprotected glycosides. Furthermore, mechanistic studies were consistent with a highly dissociative concerted S_Ni mechanism.

収録刊行物

• 有機合成化学協会誌

  有機合成化学協会誌 78 (3), 221-231, 2020-03-01

  公益社団法人 有機合成化学協会

キーワード

• glycosylation
• boronic acid
• borinic acid
• regioselective
• stereoselective
• 1,2-<i>cis</i>-glycoside
• unprotected glycoside
• natural glycoside
• organoboron catalyst
• direct modification

詳細情報

• CRID: 1390572174428416384
• NII論文ID: 40022181855
• NII書誌ID: AN0024521X
• DOI: 10.5059/yukigoseikyokaishi.78.221
• ISSN: 18836526
• ISSN: 00379980
• NDL書誌ID: 030301101
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I030301101
• Web Site: https://www.jstage.jst.go.jp/article/yukigoseikyokaishi/78/3/78_221/_pdf
• 本文言語コード: ja
• データソース種別:
  • JaLC
  • NDL
  • Crossref
  • CiNii Articles
  • KAKEN
• 抄録ライセンスフラグ: 使用不可