Development of mildly introducible PMB-substitute protecting groups and their application to the total synthesis

2017 Fiscal Year Final Research Report

• Project/Area Number: 15K21210
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Multi-year Fund
• Research Field: Biomolecular chemistry; Synthetic chemistry
• Research Institution: Kyushu University
• Principal Investigator: Torikai Kohei 九州大学, 理学研究院, 助教 (20456990)
• Project Period (FY): 2015-04-01 – 2018-03-31
• Keywords: 保護基 / ナフチルメトキシメチル基 / 選択的除去

Outline of Final Research Achievements

In this work, "1-NAPOM" and "2-NAPOM" groups were developed as protecting groups, that work in the field of organic chemistry to suppress the reactivity of alcohols and thiols, and which can be cleaved in necessity. NAPOM groups are superior to the conventional members of benzyl and benzyloxymethyl families in that; i) it is orthogonally cleavable in the presence of benzyl and benzyloxymethyl groups; ii)it is removable in mild conditions (mildly basic, room temperature); and iii) NAPOMCl, an introducing reagent of NAPOM groups, is a stable and isolable solid, which can be stored and therefore be commerciallized.
Besides, it was revealed that these protecting groups can be applicable to the glyco- and peptide-chemistry. Therefore, NAPOM groups are expected to be useful tools in the field of organic chemistry, in the near future.

Free Research Field

有機合成化学，天然物有機化学，生物有機化学