1374871-13-2

Upstream product

• 16758-34-2 1-thiophenyl-β-D-galactopyranoside 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 71676-30-7 phenyl 4,6-di-O-benzylidene-1-thio-β-D-galactopyranoside 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 4163-60-4 β-D-galactose peracetate 

Downstream Products

• 1374871-15-4 4,6-O-benzylidene-2,3-bis-O-(tert-butyldimethylsilyl)-1-[(R(s))-phenylsulfinyl]-β-D-galactopyranoside 
• 1374871-16-5 4,6-O-benzylidene-2,3-bis-O-(tert-butyldimethylsilyl)-1-[(S(s))-phenylsulfinyl]-β-D-galactopyranoside 
• 1374871-14-3 phenyl 4,6-O-benzylidene-2,3-bis-(O-tert-butyldimethylsilyl)-1-thio-β-D-galactopyranoside 
• 213997-89-8 phenyl 3-O-benzoyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside 
• 804566-04-9 phenyl 2-O-benzoyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside 

Relevant academic research and scientific papers

Total Synthesis of the Echinodermatous Ganglioside LLG-3 Possessing the Biological Function of Promoting the Neurite Outgrowth

A total synthesis of echinodermatous ganglioside LLG-3 with neuritogenic activity was accomplished by a convergent strategy. The synthesis of 2-hydroxyethyl 8-O-Me-α-sialoside 2 was started from the phenyl 7,8-di-O-Pico-thiosialoside 5, which can be chemoselectively removed the picoloyl group, and then the methyl group in 8-O-MeNeu5Ac moiety was chemoselectively prepared using TMSCHN2/FeCl3. For preparation of the terminal disialic unit, oxidative amidation was initially utilized by our group to efficiently construct the α(2,11) linkage of 8-O-Me-Neu5Acα(2,11)Neu5Gc. Herein, we also demonstrate that the synthesized ganglioside LLG-3 exhibited the neuritogenic activity toward the primary cortical neurons and that biological activity is superior to that of ganglioside DSG-A.

Copper(I)-mediated 1,2-metallate rearrangements of 1-metallated glycals

1,2-Metallate rearrangements involving reaction of 1-metallated glycals with organolithium reagents under copper(I) mediation give alkenylpolyol chains in 45-91% yield (19 examples). The reaction was applied to a formal synthesis of KRN7000 as well as a synthesis of a 5,6-ceramide derivative. Georg Thieme Verlag Stuttgart · New York.