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Introduction of 4-Chlorophenyl: A Protecting Group for the Hydroxy Function
Synlett ( IF 2 ) Pub Date : 2018-04-13 , DOI: 10.1055/s-0036-1591984
Koichi Fukase 1 , Yuji Otsuka 1, 2 , Toshihiro Yamamoto 1, 2
Affiliation  

4-Chlorophenyl ether was utilized as a new protecting group for the hydroxy function. This group was readily introduced to a sugar hydroxy group by using diaryliodonium triflate. Regioselective introduction of this protecting group at the vicinal cis -diol was achieved by using a copper catalyst and diaryliodonium triflate. This protecting group is stable under the Lewis acidic conditions of glycosylation, but it can be readily removed by the initial conversion into the corresponding 4-methoxyphenyl ether with use of a Pd catalyst, followed by oxidation with ammonium cerium (IV) nitrate [(NH 4 ) 2 Ce(NO 3 ) 6 ] (CAN).

中文翻译:

介绍 4-氯苯基:羟基官能团的保护基团

4-氯苯基醚被用作羟基官能团的新保护基团。通过使用二芳基碘鎓三氟甲磺酸盐,可以很容易地将该基团引入糖羟基。通过使用铜催化剂和三氟甲磺酸二芳基碘鎓,在邻位顺式二醇处区域选择性地引入该保护基团。该保护基团在糖基化的路易斯酸性条件下是稳定的,但可以通过使用 Pd 催化剂初始转化为相应的 4-甲氧基苯基醚,然后用硝酸铈 (IV) 铵氧化 [(NH 4 ) 2 Ce(NO 3 ) 6 ] (CAN)。
更新日期:2018-04-13
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