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Synthesis 2022; 54(12): 2825-2838
DOI: 10.1055/a-1751-1225
paper

4-(tert-Butyldiphenylsilyloxy)-2,2-dimethylbutanoyl: An Easily Removable Pivaloyl-Type Protecting Group with High Orthogonality

Qishuai Li
a   Key Laboratory of Marine Medicine, Chinese Ministry of Education, Shandong Provincial Key Laboratory of Glycoscience and Glycotechnology, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, P. R. of China
,
Yong Su
a   Key Laboratory of Marine Medicine, Chinese Ministry of Education, Shandong Provincial Key Laboratory of Glycoscience and Glycotechnology, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, P. R. of China
,
Zhi Qiao
a   Key Laboratory of Marine Medicine, Chinese Ministry of Education, Shandong Provincial Key Laboratory of Glycoscience and Glycotechnology, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, P. R. of China
,
Jianjun Wang
a   Key Laboratory of Marine Medicine, Chinese Ministry of Education, Shandong Provincial Key Laboratory of Glycoscience and Glycotechnology, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, P. R. of China
,
Peng Wang
a   Key Laboratory of Marine Medicine, Chinese Ministry of Education, Shandong Provincial Key Laboratory of Glycoscience and Glycotechnology, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, P. R. of China
,
Sumei Ren
a   Key Laboratory of Marine Medicine, Chinese Ministry of Education, Shandong Provincial Key Laboratory of Glycoscience and Glycotechnology, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, P. R. of China
b   Laboratory for Marine Drugs and Bioproducts, Pilot National Laboratory for Marine Science and Technology, Qingdao 266237, P. R. of China
,
Ni Song
a   Key Laboratory of Marine Medicine, Chinese Ministry of Education, Shandong Provincial Key Laboratory of Glycoscience and Glycotechnology, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, P. R. of China
b   Laboratory for Marine Drugs and Bioproducts, Pilot National Laboratory for Marine Science and Technology, Qingdao 266237, P. R. of China
,
Ming Li  ∗
a   Key Laboratory of Marine Medicine, Chinese Ministry of Education, Shandong Provincial Key Laboratory of Glycoscience and Glycotechnology, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, P. R. of China
b   Laboratory for Marine Drugs and Bioproducts, Pilot National Laboratory for Marine Science and Technology, Qingdao 266237, P. R. of China
› Author AffiliationsWe 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).
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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 acid

Supporting 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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