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Synthesis 2022; 54(12): 2825-2838
DOI: 10.1055/a-1751-1225
DOI: 10.1055/a-1751-1225
paper
4-(tert-Butyldiphenylsilyloxy)-2,2-dimethylbutanoyl: An Easily Removable Pivaloyl-Type Protecting Group with High Orthogonality
We are grateful for financial support from the National Natural Science Foundation of China (Grant No. 21977088), the National Natural Science Foundation of China-Shandong Joint Foundation (Grant No. U1906213), and the Natural Science Foundation of Shandong Province (Grant No. ZR2018MB015).
Abstract
Protecting groups play multiple and vital roles during the synthesis of carbohydrates and other natural products. We herein report the installation and orthogonal cleavage, under mild conditions, of a 4-(tert-butyldiphenylsilyloxy)-2,2-dimethylbutanoyl (BDMB) group as a sterically hindered pivaloyl-type hydroxy protecting group. The compatibility of this substituent with the removal of other protecting groups is also investigated. Due to its advantageous properties, BDMB is anticipated to function as a valuable agent for masking hydroxy groups.
Keywords
4-(tert-butyldiphenylsilyloxy)-2,2-dimethylbutanoyl - carbohydrates - protecting groups - assisted cleavage - tetrabutylammonium fluoride - acetic acidSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1751-1225.
- Supporting Information
Publication History
Received: 11 January 2022
Accepted after revision: 26 January 2022
Accepted Manuscript online:
26 January 2022
Article published online:
23 March 2022
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