197016-48-1Relevant academic research and scientific papers
Highly β-selective O-glucosidation due to the restricted twist-boat conformation
Okada, Yasunori,Mukae, Tatsuya,Okajima, Kotaro,Taira, Miyoko,Fujita, Mari,Yamada, Hidetoshi
, p. 1573 - 1576 (2008/02/03)
Equation presented Ethyl 1 -thlo-2,3,4,6-tetrakis-O-triisopropylsilyl- β-D-glucopyranoside, ethyl 6-O-benzyl-1 -thio-2,3,4-tris-O- triisopropylsilyl-β-D-glucopyranoside, and ethyl 6-Opivaloyl-1-thio-2,3,4- tris-O-triisopropylsilyl-β-D-glucopyranoside induced highly β-selective O-glucosidations. Among them, the 6-O-pivaloylated substrate provided the best selectivity up to α/β = 3:97 with cyclohexylmethanol, and the substrate was used for glucosidations with secondary and tertiary alcohols in a highly β-selective manner. The selectivity would be caused by the twist-boat conformation of the pyranose; this is the first β-selective O-glucosidation based on conformational control of the pyranose ring.
