Regioselective glycosylation of fully unprotected sugars by means of molecular recognition using arylboronic acid

使用芳基硼酸通过分子识别对完全未受保护的糖进行区域选择性糖基化

• 批准号: 19590010
• 负责人: NISHINO Takashi
• 金额: $ 2.83万
• 依托单位: Kitasato University
• 依托单位国家: 日本
• 项目类别: Grant-in-Aid for Scientific Research (C)
• 财政年份: 2007
• 资助国家: 日本
• 起止时间: 2007 至 2009
• 项目状态: 已结题
• 来源: https://kaken.nii.ac.jp/grant/KAKENHI-PROJECT-19590010/
• 关键词: 糖鎖; アリールボロン酸; 分子認識; グリコシル化; 無保護; 位置選択性; 合成化学

The methodology is adapted to molecular recognition of sugar structures with arylboronic acids, which from 5-membered boronates from 1,2-cis-dihydroxy groups, or 6-membered boronates from 1,3-dihydroxy groups. As expected glycosylation occurs on the left hydroxy group free from the boronate formation, and then the boronates are removed in situ by aqueous workup to yield various disaccharides in one-pot process.Various hexoses. eg., D-glucose, D-galactose, D-mannose were glycosylated, after boronate formation, with phenyl per-O-benzoyl-1-thio-β-D-glucopyranoside, -β-D-galactopyranoside and -α-D-mannopyranoside in the presence of promoters (NIS-TMSOTf) to furnish corresponding disaccharides ; glycosyl-β(1→6)-D-glucose, -β(1→6)-D-galactose, -βα(1,1)-D-mannoside in good yields.This method would be of significance with respect to regio- and stereoselecyive glycosylation, which might contribute to simple, one-pot preparation of various oligosaccharides of biological interest.

该方法适用于用芳基硼酸对糖结构进行分子识别，芳基硼酸来自 1,2-顺式二羟基的 5 元硼酸酯或 1,3-二羟基的 6 元硼酸酯。正如预期的那样，糖基化发生在左侧羟基上，没有形成硼酸酯，然后通过水处理原位去除硼酸酯，在一锅法中产生各种二糖。各种己糖。例如，在硼酸酯形成后，D-葡萄糖、D-半乳糖、D-甘露糖在启动子(NIS-TMSOTf)存在下用苯基过-O-苯甲酰基-1-硫代-β-D-吡喃葡萄糖苷、-β-D-吡喃半乳糖苷和-α-D-吡喃甘露糖苷进行糖基化，以提供相应的二糖；糖基-β(1→6)-D-葡萄糖、-β(1→6)-D-半乳糖、-βα(1,1)-D-甘露糖苷的收率良好。该方法对于区域和立体选择性糖基化具有重要意义，可能有助于简单、一锅法制备各种具有生物学意义的寡糖。

项目成果

One-pot, regioselective glycosylation of non-protected sugars by transient masking of hydroxyl groups with arylboronic acids

通过用芳基硼酸瞬时掩蔽羟基来对未保护的糖进行一锅、区域选择性糖基化

• 发表时间: 2008
• 作者: 谷史人;西川慧;山田祐香理;大植隆司;北畠直文;梶 英輔
• 通讯作者: 梶 英輔

Regioselective glycosylation of fully unprotected methyl hexopyranoshides by means of transient masking of hydroxyl groups with arylboronic acids

通过芳基硼酸瞬时掩蔽羟基对完全未保护的甲基吡喃酮进行区域选择性糖基化

• 发表时间: 2010
• 期刊: Tetrahedron Lettes 51
• 作者: E. Kaji;T. Nishino;K. Ishige;Y. Ohya;Y. Shirai
• 通讯作者: Y. Shirai

One-pot regioselective glycosylation of non-protected sugar by transient masking of hydroxyl groups with arylboronic acid

通过芳基硼酸瞬时掩蔽羟基对未保护糖进行一锅区域选择性糖基化

• 发表时间: 2008
• 作者: E. Kaji;K. Ishige;T. Nishino
• 通讯作者: T. Nishino

Regioselective glycosylation of fully unprotected methyl hexo-pyranoshides by means of transient masking of hydroxy groups with arylboronic acids

通过用芳基硼酸瞬时掩蔽羟基来对完全未保护的甲基己基吡喃酯进行区域选择性糖基化

• 发表时间: 2010
• 期刊: Tetrahedron Letters 51
• 作者: E.Kaji;T.Nishino;K.Ishige;Y.Ohya;Y.Shirai
• 通讯作者: Y.Shirai

アリールボロン酸の分子認識を利用した遊離糖の位置選択的グリコシル化反応の開発

利用芳基硼酸的分子识别开发游离糖的区域选择性糖基化

• 发表时间: 2010
• 作者: 白井裕子;石毛宏治;山本大介;西野貴司;牧野一石;梶英輔
• 通讯作者: 梶英輔