118977-25-6Relevant articles and documents
Neoglycoprotein cancer vaccines: Synthesis of an azido derivative of GM3 and its efficient coupling to proteins through a new linker
Xue, Jie,Pan, Yanbin,Guo, Zhongwu
, p. 1599 - 1602 (2002)
A GM3 derivative having an azido group on its reducing end was synthesized in nine separate steps, and it was then conjugated to proteins by a new linker. Therefore, the azido group was reduced to a free amino group, which was followed by the introduction
Concise Synthesis of 1-Thioalkyl Glycoside Donors by Reaction of Per-O-acetylated Sugars with Sodium Alkanethiolates under Solvent-Free Conditions
Dong, Hai,Feng, Guang-Jing,Guo, Yang-Fan,Liu, Chun-Yang,Luo, Tao
, (2022/02/07)
A relatively green method for synthesizing 1-thioalkyl glycosides has been developed, where sodium alkanethiolates were used to react with per-O-acetylated sugars instead of odorous alkyl mercaptans in the presence of BF3·Et2O without the use of solvents under mild conditions. Furthermore, we found that 1,2-trans-β-thioglycosides can be converted into corresponding 1,2-cis-α-thioglycosides in the presence of trifluoromethanesulfonic acid in nonpolar solvents under mild conditions. This provides a simple and efficient new approach for synthesizing challenging 1,2-cis-α-thioglycosides.
Triflic acid-mediated synthesis of thioglycosides
Escopy, Samira,Singh, Yashapal,Demchenko, Alexei V.
supporting information, p. 8379 - 8383 (2019/09/30)
An efficient synthesis of thioglycosides from per-acetates in the presence of triflic acid is described. The developed protocol features high reaction rates and product yields. Some reactive sugar series give high efficiency in the presence of sub-stoichiometric trifluoromethanesulfonic acid (TfOH) in contrast to other known protocols that require multiple equivalents of Lewis acids to reach high conversion rates.