4.8 Article

Stereodivergent Mannosylation Using 2-O-(ortho-Tosylamido)benzyl Group

Journal

ORGANIC LETTERS
Volume 20, Issue 16, Pages 4833-4837

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.8b01979

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Funding

  1. Japan Society for the Promotion of Science [16H06290, 26350966, 15H02443]
  2. RIKEN Special Postdoctoral Program

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We report a novel strategy for obtaining both anomers from a single mannosyl donor equipped with a C2-o-TsNHbenzyl ether (2-O-TAB) by switching reaction conditions. In particular, the formation of various beta-mannosides was achieved with high selectivity by using a mannosyl phosphite in the presence of ZnI2.

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