68027-31-6

Upstream product

• 34212-64-1 methyl 2,3,4-tri-O-benzyl-α-D-mannopyranoside 
• 155205-39-3 methyl 2,3,4-tri-O-benzyl-6-deoxy-α-D-altro-heptopyranosylurononitrile 
• 68027-27-0 methyl 2,3,4-tri-O-benzyl-α-D-altropyranoside 
• 40653-15-4 methyl 2,3,4-tri-O-benzyl-α-D-manno-hexodialdo-1,5-pyranoside 
• 40653-17-6 methyl 2,3,4-tri-O-benzyl-6-deoxy-6-C-formyl-α-D-mannopyranoside 
• 40653-16-5 methyl 2,3,4-tri-O-benzyl-7-O-methyl-6-deoxy-α-D-manno-hept-6-enopyranoside 
• 586-96-9 Nitrosobenzene 
• 174155-13-6 methyl 6-deoxy-2,3,4-tri-O-benzyl-α-D-gluco-hepto-1,7-dialdopyranoside 
• 122588-56-1 (2S,3S,4S,5R,6R)-3,4,5-Tris-benzyloxy-2-methoxy-6-vinyl-tetrahydro-pyran 
• 540500-97-8 methyl 2,3,4-tri-O-benzyl-6-deoxy-6-(1,3-dithianyl)-α-D-mannopyranoside 
• 221545-35-3 ((2R,3R,4S,5S,6S)-3,4,5-tris(benzyloxy)-6-methoxytetrahydro-2H-pyran-2-yl)methyl trifluoromethanesulfonate 
• 155205-41-7 methyl 2,3,4-tri-O-benzyl-6-deoxy-α-D-manno-heptopyranosylurononitrile 

Downstream Products

• 540500-99-0 methyl 2,3,4-tri-O-benzyl-6-deoxy-7-O-methanesulfonyl-α-D-mannoheptopyranoside 
• 540501-02-8 methyl 2,3,4-tri-O-benzyl-6-deoxy-7-bromo-α-D-mannoheptopyranoside 

Relevant academic research and scientific papers

General Homologation Strategy for Synthesis of l -glycero- and d -glycero-Heptopyranoses

A general and stereospecific homologation strategy for the synthesis of heptopyranosides is reported. The strategy employs the Wittig olefination and proline-catalyzed α-aminoxylation to achieve one carbon elongation and stereoselective hydroxylation at the C6 position, respectively. The l-glycero- and d-glycero-heptopyranosides can be obtained with nearly perfect stereoselectivity. Further study reveals the difference in the chemical shift of the C6 proton of l/d-glycero-heptopyranosyl diastereomers, which is found to be useful for assignment of the configuration of heptopyranosides.

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.

A flexible route to mannose 6-phosphonate functionalized derivatives

A new approach for the synthesis of a mannose 6-phosphonate isosteric analog of mannose 6-phosphate is reported. The mannosylphosphonate has been prepared in a multistep synthesis involving an homologation reaction of the methyl α-D-mannopyranoside followed by an Arbuzov reaction between a bromohomomannosyl derivative and the tris(trimethylsilyl)phosphite. This approach, avoiding the deprotection of dialkylphosphonate, allowed us to prepare the mannose 6-phosphonate in good yield. The described method was successfully extended to the preparation of a mannose 6-phosphonate linked to a cholesteryl moiety. This strategy affords a more general route for a wide range of functionalized mannose 6-phosphonate derivatives.

Syntheses of methyl glycosides of 6-deoxyheptoses

Methyl α-D-glycopyranosides of 6-deoxy-D-altro-heptose, 6-deoxy-D-manno-heptose, and 6-deoxy-D-talo-heptose have been prepared. Displacements of methyl 2,3,4-tri-O-benzylhexopyranoside 6-trifluoromethanesulfonates with potassium cyanide, followed by reduction of the resulting heptopyranosidurononitriles with diisobutylaluminum hydride, hydrolysis of the imine, further reduction with sodium borohydride, and catalytic O-debenzylation, give the corresponding methyl 6-deoxyheptopyranosides. Configurational change at C-4 of methyl 6-deoxy-7-O-tert-butyldiphenylsilyl-α-D-manno-heptopyranoside to give the talo isomer was effected by oxidation followed by stereoselective reduction. 1H nuclear magnetic resonance data of the glycosides, and gas chromatography of acetylated glycosides of (R)- and (S)-2-butanol serve to establish ring and enantiomeric configurations of the parent sugars when these are encountered as constituents of lipopolysaccharides or extracellular carbohydrate polymers, as in Campylobacter species.