In the presence of a catalyst generated from SnCl4 and AgClO4, or Yb(OTf)3 various glycosyl azides are synthesized in high yields with complete stereoselectivities from peracylated sugars and trimethylsilyl azide by choosing a suitable solvent such as dichloromethane or nitromethane.
1,2-trans-Ribofuranosides are stereoselectively synthesized from 1-O-trimethylsilyl ribofuranose and trimethylsilyl ethers in the presence of a catalytic amount of Me3SiOTf using Ph2Sn=S as an additive, while 1,2-cis-ribofuranosides and 1,2-cis-glucopyranosides are prepared predominantly in the coexistence of LiClO4 in the above reaction.
In the presence of a catalyst generated from SnCl4 and a silver salt, various 2-amino-2-deoxy-α-D-glucopyranosides or galactopyranosides are stereoselectively synthesized in good yields with high stereoselectivities through anomerization step starting from 1,3,4,6-tetra-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranose or galactopyranose and alkyl trimethylsilyl ethers, respectively.
In the presence of a catalytic amount of active acidic species generated from SnCl4 and AgClO4, various α-glucosides are stereoselectively synthesized in excellent yields from 1-O-2′-(2′-methoxyethoxy)acetyl-2,3,4,6-tetra-O-benzyl-D-glucopyranose and alkyl trimethylsilyl ethers. β-Glucosides are also selectively prepared by using a catalyst, generated from SiCl4 and AgClO4 in the above reaction.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.