20196-78-5Relevant academic research and scientific papers
Perfluorophenylboronic acid-catalyzed direct α-stereoselective synthesis of 2-deoxygalactosides from deactivated peracetylated d-galactal
Tatina, Madhu Babu,Moussa, Ziad,Xia, Mengxin,Judeh, Zaher M. A.
supporting information, p. 12204 - 12207 (2019/10/22)
Perfluorophenylboronic acid 1c catalyzes the direct stereoselective addition of alcohol nucleophiles to deactivated peracetylated d-galactal to give 2-deoxygalactosides in 55-88% yield with complete α-selectivity. The unprecedented results reported here a
Copper-Catalyzed Anomeric O-Arylation of Carbohydrate Derivatives at Room Temperature
Verdelet, Tristan,Benmahdjoub, Sara,Benmerad, Belkacem,Alami, Mouad,Messaoudi, Samir
, p. 9226 - 9238 (2019/08/12)
Direct and practical anomeric O-arylation of sugar lactols with substituted arylboronic acids has been established. Using copper catalysis at room temperature under an air atmosphere, the protocol proved to be general, and a variety of aryl O-glycosides have been prepared in good to excellent yields. Furthermore, this approach was extended successfully to unprotected carbohydrates, including α-mannose, and it was demonstrated here how the interaction between carbohydrates and boronic acids can be combined with copper catalysis to achieve selective anomeric O-arylation.
A One-Pot Method for Removal of Thioacetyl Group via Desulfurization under Ultraviolet Light to Synthesize Deoxyglycosides
Ge, Jian-Tao,Zhou, Lang,Luo, Tao,Lv, Jian,Dong, Hai
supporting information, p. 5903 - 5906 (2019/08/26)
We herein developed an efficient method for removing thioacetyl to synthesize acylated deoxy glycosides in a one-pot reaction, where the thioacetyl was selectively deacetylated by hydrazine hydrate in DMF within 2-5 min at room temperature, followed by de
Facile TMSOTf-catalyzed preparation of 2-deoxy α-O-aryl-D-glycosides from glycosyl acetates
Yang, Guofang,Wang, Qingbing,Luo, Xiaosheng,Zhang, Jianbo,Tang, Jie
, p. 453 - 456 (2012/10/29)
2-Deoxy a-O-aryl glycosides were conveniently obtained by reaction of 2-deoxy-glycosyl acetates with phenols in the presence of TMSOTf as the promoter. The current method provides the O-aryl glycosides with good to excellent yields, and sole alpha selecti
Aluminium triflate catalysed O-glycosidation: Temperature-switched selective Ferrier rearrangement or direct addition with alcohols
Williams, D. Bradley G.,Simelane, Sandile B.,Kinfe, Henok H.
supporting information; experimental part, p. 5636 - 5642 (2012/08/07)
A temperature-controlled mechanism switch between the Al(OTf) 3-catalysed direct addition of alcohols or the Ferrier rearrangement reactions in some glycals is presented. The scope and limitations are investigated as are the influence of the st
Direct Preparation of 2-Deoxy-D-glucopyranosides from Glucals without Ferrier Rearrangement
Bolitt, Veronique,Mioskowski, Charles,Lee, S.-G.,Falck, J. R.
, p. 5812 - 5813 (2007/10/02)
An efficient catalytic procedure for the preparation of 2-deoxyglucosides from glucals without allylic or Ferrier rearrangement using triphenylphosphine hydrobromide and a wide variety of hydroxylic nucleophiles is described.
