180591-25-7

Upstream product

• 54503-65-0 2,2-dimethyl-6-(trityloxymethyl)tetrahydrofuro[3,4-d][1,3]dioxol-4-ol 
• 3556-64-7 N,N-diethylcarbamoylmethyl dimethylsulfonium chloride 
• 688321-37-1 N,N-diethyl 2,3-anhydro-4,5-O-isopropylidene-7-O-trityl-D-altro-6-heptulosamide 
• 180591-23-5 (2S,3R)-3-[(4S,5R)-5-((R)-1-Hydroxy-2-trityloxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-oxirane-2-carboxylic acid diethylamide 

Relevant academic research and scientific papers

Asymmetric synthesis of 2,3-epoxyamides by reacting monosaccharide derivatives with stabilised sulphur ylides generated in-situ: Two-phase method and configurational assignations

The reaction of 2,3-O-isopropylidene-D-glyceraldehyde 1, 2,4-ethylidene D-threose 7, or 2,3:4,5-di-O-isopropylidene-D-arabinose 9 with N,N-dimethyl-carbamoylmethyl dimethyl sulphonium chloride and a 10-50% solution of sodium hydroxyde gave the corresponding 2,3-epoxyamides 5,8 and 10, and the reaction of 1, or 5-O-trityl-2,3-O-isopropylidene-D-ribofuranose 13 with N,N-diethylcarbamoylmethyl dimethyl sulphonium chloride and a 10-50% solution of sodium hydroxyde gave the corresponding 2,3-epoxyamides 4 and 14, respectively, with high yields and variable stereoselectivity.

Syntheses of sugar-related pyrrolidine derivatives by reductive amination reactions

Several pyrrolidine iminosugar derivatives have been stereoselectively synthesised from a chiral keto-epoxyamide, by reductive amination procedures. An unexpected cyanide addition was observed when a mixture of SnCl2 and NaCNBH3 was employed.