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2,6-Bis(trifluoromethyl)phenylboronic Esters as Protective Groups for Diols: A Protection/Deprotection Protocol for Use under Mild Conditions
Organic Letters ( IF 4.9 ) Pub Date : 2018-09-18 00:00:00 , DOI: 10.1021/acs.orglett.8b02427
Naoyuki Shimada 1 , Sari Urata 1 , Kenji Fukuhara 1 , Takao Tsuneda 2 , Kazuishi Makino 1
Affiliation  

The application of 2,6-bis(trifluoromethyl)phenyl boronic acid (o-FXylB(OH)2; o-FXyl = 2,6-(CF3)2C6H3) as a recoverable and reusable protective agent for diols is described. The resulting cyclic boronic esters are water- and air-stable and tolerant to various organic transformations. Moreover, they can be deprotected under mild conditions. This methodology was applied to the synthesis of a highly conjugated enetriyne natural product with anti-angiogenic activities.

中文翻译:

2,6-双(三氟甲基)苯基硼酸酯作为二元醇的保护基:在温和条件下使用的保护/脱保护方案

2,6-双(三氟甲基)苯基硼酸(o -FXylB(OH)2 ; o -FXyl = 2,6-(CF 32 C 6 H 3)作为可回收和可重复使用的二醇保护剂的应用描述。所得的环状硼酸酯是水和空气稳定的,并且耐受各种有机转化。而且,它们可以在温和的条件下脱保护。该方法学被用于具有抗血管生成活性的高度共轭的三烯天然产物的合成。
更新日期:2018-09-18
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