3445-71-4

Upstream product

• 530-26-7 D-Mannose 
• 74-88-4 methyl iodide 
• 67-56-1 methanol 
• 197631-81-5 phenyl 2,3,4,6-tetra-O-methyl-1-deoxy-1-thio-α-D-mannopyranoside S-oxide 
• 95690-50-9 7-Hydroxy-5-methoxy-2-[4-((2S,3R,4R,5R,6R)-3,4,5-trimethoxy-6-methoxymethyl-tetrahydro-pyran-2-yloxy)-phenyl]-chromen-4-one 
• 95690-54-3 5-Methoxy-7-((2S,3R,4R,5R,6R)-3,4,5-trimethoxy-6-methoxymethyl-tetrahydro-pyran-2-yloxy)-2-[4-((2S,3R,4R,5R,6R)-3,4,5-trimethoxy-6-methoxymethyl-tetrahydro-pyran-2-yloxy)-phenyl]-chromen-4-one 
• 95690-55-4 Acetic acid (2R,3R,4R,5R,6S)-3,4,5-trimethoxy-6-{5-methoxy-4-oxo-2-[4-((2S,3R,4R,5R,6R)-3,4,5-trimethoxy-6-methoxymethyl-tetrahydro-pyran-2-yloxy)-phenyl]-4H-chromen-7-yloxy}-tetrahydro-pyran-2-ylmethyl ester 

Downstream Products

• 3149-62-0 methyl 2,3,4,6-tetra-O-methyl-α-D-mannopyranoside 
• 492-93-3 1,5-anhydro-D-mannitol 

Relevant academic research and scientific papers

TOLL-LIKE RECEPTOR 9 AGONISTS

The present invention provides TLR9 agonists comprising, as an active ingredient, a compound represented by formula (I): (wherein a represents 0 or 1; n represents an integer of 0 to 2; m represents an integer of 0 to 5; X1 and X2 each independently represent a hydrogen atom or hydroxy; Y represents an oxygen atom or a sulfur atom; -Q1-represents -O- or the like; -Q2- represents -O- or the like; -Z- represents -O- or the like; R1, R3 and R4 each independently represent hydroxy or the like; R2 and R5 each independently represent a hydrogen atom, hydroxy or the like; and A represents 6-aminopurin-9-yl or the like) or a pharmaceutically acceptable salt thereof, and the like.

Are glycosyl triflates intermediates in the sulfoxide glycosylation method? A chemical and 1H, 13C, and 19F NMR spectroscopic investigation

The title question is addressed by low-temperature 1H, 13C, and 19F NMR spectroscopies in CD2CL2 as well as by the preparation of authentic samples from glycopyranosyl bromides and AgOTf. At -78°C glycosyl triflates are cleanly generated with either nonparticipating or particpating protecting groups at O-2. The glycosyl triflates identified in this manner were allowed to react with methanol, resulting in the formation of methyl glycosides. Glycosyl triflates were generated at -78°C in CD2Cl2 and allowed to warm gradually until decomposition was detected by 1H and 19F NMR spectroscopy. The decomposition temperature and products are functions of the protecting groups employed.

Peralkylation of Saccharides under Aqueous Conditions

Treatment of saccharides with sodium hydroxide and alkyl halides in aqueous dimethyl sulfoxide solution offers a very efficient method for the complete alkylation of saccharides in high yields.