128142-70-1Relevant articles and documents
Deprotection of silyl ethers by using SO3H silica gel: Application to sugar, nucleoside, and alkaloid derivatives
Fujii, Hideaki,Shimada, Naoyuki,Ohtawa, Masaki,Karaki, Fumika,Koshizuka, Masayoshi,Hayashida, Kohei,Kamimura, Mitsuhiro,Makino, Kazuishi,Nagamitsu, Tohru,Nagase, Hiroshi
, p. 5425 - 5429 (2017/08/11)
We applied a desilylation procedure using SO3H silica gel, with the surface modified by alkylsulfonic acid groups, to silylated sugar, nucleoside, and alkaloid derivatives. The treatment with SO3H silica gel provided desilylated products in good to excellent yield. In the reactions of sugar and nucleoside derivatives, no silyl residue was detected in the crude products, but the crude products of the reaction of alkaloids contained small amounts of silyl residues. Even though the sugar and nucleoside derivatives had a labile glycosyl and C–N bond, respectively, these bonds tolerated the reaction conditions. These outcomes suggested that the desilylation procedure using SO3H silica gel would be applicable to the deprotection of a variety of types of compounds protected by silyl groups. In a gram scale experiment, the desilylation procedure successfully proceeded without the observation of any silyl residue in the crude product.
Synthesis of a Methyl Heptaglucoside: Analogue of the Phytoalexin Elicitor from Phytophtora Megasperma
Verduyn, R.,Douwes, M.,Klein, P.A.M. van der,Moesinger, E.M.,Marel, G.A. van der,Boom, J.H. van
, p. 7301 - 7316 (2007/10/02)
The ethylthio-laminaribioside 29, prepared by regiospecific glycosylation of ethyl 4,6-O-benzylidene-1-thio-β-D-glucopyranoside (9) with 2,3,4,6-tetra-O-benzoyl-D-glucopyranosyl imidate 17 and subsequent benzoylation, could be elongated in a step-wise fas
