221189-79-3

Upstream product

• 221189-67-9 3,7-anhydro-1,2,6-trideoxy-6-C-<propyl>silyl>ethynyl>-1-C-(4-nitrophenyl)-4-O-(triisopropylsilyl)-D-glycero-D-gulo-oct-1-ynitol 
• 221189-25-9 3,7-anhydro-1,2,6-trideoxy-6-C-<propyl>silyl>ethynyl>-4-O-(triisopropylsilyl)-1-C-(trimethylsilyl)-D-glycero-D-gulo-oct-1-ynitol 
• 221189-27-1 3,7-anhydro-1,2,6-trideoxy-6-C-<propyl>silyl>ethynyl>-4-O-(triisopropylsilyl)-D-glycero-D-gulo-oct-1-ynitol 
• 221189-37-3 3,7-anhydro-1,2,6-trideoxy-6-C-<<(3-hydroxy-1,1-dimethylpropyl)dimethylsilyl>ethynyl>-4-O-(triisopropylsilyl)-1-C-(trimethylsilyl)-D-glycero-D-gulo-oct-1-ynitol 
• 221189-23-7 1,6-anhydro-4-deoxy-4-C-propyl>silyl>ethynyl>-2-O-(triisopropylsilyl)-β-D-glucopyranose 
• 221189-59-9 3,7-anhydro-1,2,6-trideoxy-6-C-<(4-nitrophenyl)ethynyl>-4-O-(triisopropylsilyl)-1-C-(trimethylsilyl)-D-glycero-D-gulo-oct-1-ynitol 
• 221189-62-4 3,7-anhydro-1,2,6-trideoxy-6-C-<(4-nitrophenyl)ethynyl>-4-O-(triisopropylsilyl)-D-glycero-D-gulo-oct-1-ynitol 
• 167646-61-9 3,7-anhydro-1,1,2,2-tetradehydro-1,2,6-trideoxy-6-C-ethynyl-4-O-(triisopropylsilyl)-1-C-(trimethylsilyl)-D-glycero-D-gulo-octitol 
• 636-98-6 p-nitrobenzene iodide 
• 221189-64-6 3,7-anhydro-1-C-bromo-1,2,6-trideoxy-6-C-<(4-nitrophenyl)ethynyl>-4-O-(triisopropylsilyl)-D-glycero-D-gulo-oct-1-ynitol 
• 221189-70-4 3,7-anhydro-1,2,6-trideoxy-6-C-<<(3-hydroxy-1,1-dimethylpropyl)dimethylsilyl>ethynyl>-1-C-(4-nitrophenyl)-4-O-(triisopropylsilyl)-D-glycero-D-gulo-oct-1-ynitol 

Relevant academic research and scientific papers

Oligosaccharide analogues of polysaccharides: Part 16: Cross-coupling of partially protected dialkynyl monosaccharides

The dependency of the cross-coupling of orthogonally C-protected dialkynyl monosaccharides on the nature of the coupling partners has been studied. The required dialkyne 5 was synthesized from levoglucosan in six steps and 39% overall yield and transformed into 7, 10, 12, 13, and 14 by orthogonal C-deprotection and bromination (Scheme 1). Optimization of the conditions of their cross-coupling to 16 showed that yields were higher for the coupling of the propargylic bromoalkyne 10 than for the homopropargylic bromoalkyne 14 (Scheme 2). Deprotection of 16 gave the nano-crystalline dimer 20. To obtain more highly crystalline products, the monomers 7 and 13 were coupled with 1-iodo-4-nitrobenzene to the arylated monomers 21 and 24 (Scheme 3). The 4-NO2C6H4 substituent lowered the yield of the dimerizations to the mono- and diarylated dimers 26-28 (Scheme 4) but had no effect on crystallinity.