58530-86-2

Upstream product

• 83-87-4 D-Mannose pentaacetate 
• 108549-23-1 Dibenzyl N,N-diisopropylphosphoramidite 
• 572-09-8 2,3,4,6-tetra-O-acetyl-D-mannopyranosyl bromide 
• 1623-08-1 phosphoric acid dibenzyl ester 
• 3947-62-4 2,3,4,6-tetra-O-acetyl-D-mannopyranose 
• 50651-75-7 silver dibenzylphosphate 
• 13242-53-0 acetobromomannose 

Relevant academic research and scientific papers

Chemical synthesis of the innate immune modulator – bacterial D-glycero-β-D-manno-heptose-1,7-bisphosphate (HBP)

The bacterial metabolite and potent innate immune modulator D-glycero-β-D-manno-heptose-1,7-bisphosphate (HBP) and its α-configured counterpart D-glycero-α-D-manno-heptose-1,7-bisphosphate were synthesized via stereoselective anomeric phosphorylation of the peracetylated D,D-heptose 7-dibenzylphosphate by exploiting different nucleophilicity of equatorial and axial lactols in the D-manno-series. We also report a novel approach for anomeric phosphorylation using modified Mitsunobu reaction conditions and provide the first full structural characterization of HBP. The first chemical synthesis of HBP offers access to an anomerically pure structurally defined probe for biological studies and to a lead compound operating as a powerful stimulator of intracellular signaling for possible therapeutic immunomodulation.

Reliable synthesis of various nucleoside diphosphate glycopyranoses

A reliable and high yielding synthetic pathway for the synthesis of the biologically highly important class of nucleoside diphosphate sugars (NDP-sugars) was developed by using various cycloSal-nucleotides 1 and 9 as active ester building blocks. The reaction with anomerically pure pyranosyl1-phosphates 2 led to the target NDP-sugars 20-45 in a nucleophilic displacement reaction, which cleaves the cycloSal moiety in anomerically pure forms. As nucleosides cytidine, uridine, thymi-dine, adenosine, 2′-deoxy-guanosine and 2′,3′-dideoxy-2′,3′- didehydrothymidine were used while the phosphates of D-glucose, D-galactose, D-mannose, DNAc-glucosamine, D-NAc-galactosamine, D-fucose, L-fucose as well as 6deoxy-D-gulose were introduced.

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.

Efficient synthesis of nucleoside diphosphate glycopyranoses

(Chemical Equation Presented) Short and sweet: A new, short synthetic pathway for the synthesis of the enormously important class of nucleoside diphosphate sugars (NDP sugars) was developed using cyclo-saligenyl (cycloSal) nucleosyl phosphate triesters as

Mono, di and tri-mannopyranosyl phosphates as mannose-1-phosphate prodrugs for potential CDG-Ia therapy

An efficient and convergent method for the synthesis of mannose-1-phosphate prodrugs is described as a potential therapy for congenital disorders of glycosylation-Ia (CDG-Ia). The key feature of the proposed approach is the silver assisted nucleophilic substitution of 2,3,4,6-tetra-O-protected-α-d-mannopyranosyl bromides with various silver phosphate salts to afford mono, di, and tri-mannopyranosyl phosphates. A preliminary biological evaluation of the synthesized phosphate prodrugs has been carried out.