71074-76-5Relevant academic research and scientific papers
Highly diastereoselective 1,2-dichlorination of glycals using NCS/PPh 3: Study of substituent and solvent effects
Hussain, Altaf,Mukherjee, Debaraj
, p. 1133 - 1139 (2014/02/14)
Highly diastereoselective 1,2-dichlorination of glycals has been achieved at room temperature conditions in good to excellent yields using a milder, more convenient, less hazardous reagent combination NCS/PPh3 giving only one major product out of four possible diastereomers [either α-gluco (2) or α-manno (4)] depending upon the substituents. The diastereoselectivity is maximum (100% α/β-selectivity as well as cis/trans selectivity) for d-galactal and l-rhamnal derivatives. Detailed studies showed that solvent and substituent effects play a significant role in determining the product distribution.
N -Halosuccinimide/AgNO3-efficient reagent systems for one-step synthesis of 2-haloglycals from glycals: Application in the synthesis of 2C-branched sugars via heck coupling reactions
Dharuman, Suresh,Vankar, Yashwant D.
, p. 1172 - 1175 (2014/03/21)
An expedient one-step synthesis of 2-iodoglycals and 2-bromoglycals from glycals using NIS/AgNO3 and NBS/AgNO3 as reagent systems has been developed. The utility of these 2-haloglycals has been demonstrated by converting them into 2C
The lithiation of 2-chloroglucal derivatives
Boyd, Ewan,Hallett, Michael R.,Jones, Ray V.H.,Painter, James E.,Patel, Prakash,Quayle, Peter,Waring (née Potts), Anita J.
, p. 8337 - 8341 (2007/10/03)
Lithiation of 2-chloroglucal derivatives provides ready access to the corresponding 1-lithioglucals which undergo a variety of serve useful intermediates for further elaboration of the carbohydrate nucleus. Removal of the 2-chloro substituent may be affected using a Birch-type reduction.
