A one-pot synthetic method for the hetero-bifunctionalization of α-cyclodextrin at the secondary hydroxyl side with high clockwise-counterclockwise selectivity

Xi Huang; Shun Yasunaga; Makoto Fukudome; Wen-Hua Chen; De-Qi Yuan

doi:10.1039/c7ob00719a

A one-pot synthetic method for the hetero-bifunctionalization of α-cyclodextrin at the secondary hydroxyl side with high clockwise-counterclockwise selectivity

Org Biomol Chem. 2017 May 16;15(19):4077-4080. doi: 10.1039/c7ob00719a.

Authors

Xi Huang¹, Shun Yasunaga, Makoto Fukudome, Wen-Hua Chen, De-Qi Yuan

Affiliation

¹ Faculty of Pharmaceutical Sciences, Kobe Gakuin University, 1-1-3 Minatojima, Chuo-ku, Kobe 650-8586, Japan. deqiyuan@pharm.kobegakuin.ac.jp.

PMID: 28466912
DOI: 10.1039/c7ob00719a

Abstract

α-Cyclodextrin and 3,3'-benzophenonedisulfonylimidazole in a unimolecular ratio were stirred at 40 °C for 1 h in the presence of a catalytic amount of Cs₂CO₃ in DMF, and then treated with sodium hydroxide to give 2^A,3^A-mannoepoxy-2^B-sulfonyl-α-cyclodextrin in 14% isolated yield. The isomer with the reversed saccharide sequence was not detected.