4-(tert-Butyldiphenylsilyloxy)-2,2-dimethylbutanoyl: An Easily Removable Pivaloyl-Type Protecting Group with High Orthogonality-Reference-Cited by-同舟云学术

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

Published:2022-01-26 Issue:12 Volume:54 Page:2825-2838
ISSN:0039-7881
Container-title:Synthesis
language:en
Short-container-title:Synthesis

Author:

Li Ming¹²^ORCID,Li Qishuai¹,Su Yong¹,Qiao Zhi¹,Wang Jianjun¹,Wang Peng¹,Ren Sumei¹²,Song Ni¹²

Affiliation:

1. 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

2. Laboratory for Marine Drugs and Bioproducts, Pilot National Laboratory for Marine Science and Technology

Abstract

AbstractProtecting 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.

Funder

National Natural Science Foundation of China

National Natural Science Foundation of China-Shandong Joint Foundation

Natural Science Foundation of Shandong Province

Publisher

Georg Thieme Verlag KG

Subject

Organic Chemistry,Catalysis

Link

http://www.thieme-connect.de/products/ejournals/pdf/10.1055/a-1751-1225.pdf

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