126461-54-9Relevant articles and documents
Chiral acidic amino acids as tethers for intramolecular glycosylation
Fukushima, Katsuya,Kikuma, Takashi,Takeda, Yoichi
, p. 283 - 307 (2021/12/30)
Intramolecular glycosylation with peptides as tethers is attractive for the synthesis of oligosaccharides because conjugation between the amino acids present in the tethers is facile. However, few studies have been published about the effects of the amino
Picoloyl protecting group in synthesis: Focus on a highly chemoselective catalytic removal
Bandara, Mithila D.,Demchenko, Alexei V.,Geringer, Scott A.,Mannino, Michael P.
, p. 4863 - 4871 (2020/07/13)
The picoloyl ester (Pico) has proven to be a versatile protecting group in carbohydrate chemistry. It can be used for the purpose of stereocontrolling glycosylations via an H-bond-mediated Aglycone Delivery (HAD) method. It can also be used as a temporary protecting group that can be efficiently introduced and chemoselectively cleaved in the presence of practically all other common protecting groups used in synthesis. Herein, we will describe a new method for rapid, catalytic, and highly chemoselective removal of the picoloyl group using inexpensive copper(ii) or iron(iii) salts. This journal is
A simple and useful synthetic protocol for selective deprotection of tert-butyldimethylsilyl (TBS) ethers
Khan, Abu T.,Ghosh, Subrata,Choudhury, Lokman H.
, p. 2198 - 2204 (2007/10/03)
A wide variety of tert-butyldimethylsilyl ethers 1 can be easily cleaved to the corresponding parent hydroxyl compound 2 in the presence of 5 mol % of acetonyltriphenylphosphonium bromide (ATPB) at room temperature. In addition, tert-butyldiphenylsilyl ethers can also be cleaved by using 20 mol % of the same catalyst. Alkyl tert-butyldimethylsilyl ethers can be deprotected to the hydroxyl compounds chemoselectively in the presence of aryl tert- butyldimethylsilyl ethers. Some of the major advantages are mild reaction conditions, no aqueous workup, high efficiency and chemoselectivity and compatibility with other protecting groups; no brominations occur in the aromatic ring under these experimental conditions. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.