131070-64-9

Upstream product

• 116386-28-8 1,2-dideoxy-3,4:5,6-di-O-isopropylidene-1-nitro-2-C-(phenylthio)methyl-D-mannitol 
• 110085-92-2 (4S,5R,4'R)-2,2,2',2'-Tetramethyl-5-((R)-2-nitro-cyclopropyl)-[4,4']bi[[1,3]dioxolanyl] 
• 108-98-5 thiophenol 

Downstream Products

• 131070-65-0 2-C-acetamidomethyl-2-deoxy-3,4;5,6-di-O-isopropylidene-1-S-phenyl-1-thio-D-glucitol 
• 131070-66-1 2-C-(N,N-diacetylamino)methyl-2-deoxy-3,4;5,6-di-O-isopropylidene-1-S-phenyl-1-thio-D-glucitol 
• 131070-48-9 2-C-(N,N-diacetylamino)methyl-1-chloro-2-deoxy-3,4;5,6-di-O-isopropylidene-1-S-phenyl-1-thio-D-glucitol 
• 131070-49-0 2-C-acetamidomethyl-1-O-acetyl-2-deoxy-3,4;5,6-di-O-isopropylidene-1-S-phenyl-1-thio-D-glucitol 
• 131070-53-6 2-C-acetamidomethyl-1,2-dideoxy-3,4;5,6-di-O-isopropylidene-1-C-phenylsulfinyl-D-glucitol 

Relevant academic research and scientific papers

Synthetically useful transformations of a branched-chain, deoxynitro-1-thio-D-glucitol, including a novel mode of 1-thioglycoside formation

2-Deoxy-3,4;5,6-di-O-isopropylidene-2-C-(nitromethyl)-1-S-phenyl-1-thio-D-glucitol (2), obtainable from D-mannose in several steps with good overall yield, was converted into the corresponding sulfoxide, α-chlorosulfide, α-acetoxysulfide, and analogous 2-C-(acetamido)methyl derivatives.Mild hydrolysis of the 1-chloro derivative of 2 gave a 2-deoxy-2-C-methylene-aldehydo sugar 3,4;5,6-diacetal by concomitant elimination of nitrous acid, whereas a 2-deoxy-2-C-(nitromethyl)-D-glucitol 3,4;5,6-diacetal was obtained under reducing conditions.Pummerer rearrangement of the sulfoxide derived from 2 gave, depending on the reaction conditions, the corresponding α-acetoxysulfide or phenyl 2-deoxy-2-C-(nitromethyl)-1-thio-β-D-glucopyranoside 3,4,6-triacetate.