Department of Chemistry, Indian Institute of Technology Patna, Bihta, 801106, Bihar, India.
Chem Asian J. 2019 Dec 13;14(24):4651-4658. doi: 10.1002/asia.201900888. Epub 2019 Aug 13.
Stereoselective synthesis of deoxyglycosides has been achieved from benchtop stable and easily synthesizable deoxy-phenylpropiolate glycosides (D-PPGs) using gold(III) salt as catalyst under external additive-free conditions. Under a simple catalytic system, D-PPGs reacted with a variety of sugar and non-sugar acceptors to produce majorly α-stereoselective O/N-deoxyglycosides in good to excellent yields and regenerate easily separable and reusable phenylpropiolic acid. Deoxy-PPGs containing armed and disarmed groups survived well under the optimized reaction conditions. In addition, the orthogonal nature of D-PPGs was showcased, and 1,1'-linked trehalose-type sugar was also synthesized.
通过使用金(III)盐作为催化剂，在无外加添加剂的条件下，从台式稳定且易于合成的脱氧苯丙炔酸糖苷（D-PPGs）中实现了立体选择性合成脱氧糖。在简单的催化体系中，D-PPG 与各种糖和非糖受体反应，以良好至优异的产率生成主要为α-立体选择性的 O/N-脱氧糖苷，并再生易于分离和可重复使用的苯丙炔酸。在优化的反应条件下，含有武装和解除武装基团的脱氧-PPG 也能很好地存活。此外，还展示了 D-PPG 的正交性质，并合成了 1,1'-连接的海藻糖型糖。
