2-Naphthylmethoxymethyl as a Mildly Introducible and Oxidatively Removable Benzyloxymethyl-Type Protecting Group
2-Naphthylmethoxymethyl as a Mildly Introducible and Oxidatively Removable Benzyloxymethyl-Type Protecting Group
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2-萘基甲氧基甲基作为可温和引入且可氧化去除的苄氧基甲基型保护基团
DOI：
10.1021/acs.orglett.5b01408
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发表时间：
2015
期刊：
影响因子：
5.2
通讯作者：
K.
中科院分区：
文献类型：
--
作者：
Sato;T.; Oishi;T.; Torikai;K.
2-萘甲氧甲基（NAPOM）是为了保护各种羟基（包括酚羟基和羧基）和巯基而开发的。NAPOM基团可以在极其温和的条件下（萘甲氧基甲基氯，2，6-二甲基吡啶，室温）引入，而不会在1，2-二醇系统中伴随酰基迁移。此外，还实现了在萘甲基（NAP）和对甲氧基苄基（PMB）存在下NAPOM的选择性去除，以及在NAPOM存在下PMB的选择性去除。这些结果，以及其易于处理和与各种溶剂的相容性，表明NAPOM是一种新的和有用的选择作为保护基团。
2-Naphthylmethoxymethyl (NAPOM) was developed for the protection of various hydroxy (including phenolic hydroxy and carboxy) and mercapto groups. The NAPOM group can be introduced in extremely mild conditions (naphthylmethoxymethyl chloride, 2,6-lutidine, room temperature) without concomitant acyl migration in a 1,2-diol system. Furthermore, selective removal of NAPOM in the presence of naphthylmethyl (NAP) andp-methoxybenzyl (PMB) groups and, conversely, that of PMB in the presence of NAPOM were realized. These results, as well as its easy handling and compatibility with various solvents, show that NAPOM is a novel and useful choice as a protecting group.