440359-25-1

Upstream product

• 20194-18-7 sodium phenyl-methanolate 
• 26532-10-5 methyl 2,3-anhydro-α-D-lyxofuranoside 

Downstream Products

• 440359-26-2 methyl 3-O-benzyl-2,5-bis-O-di-tert-butylsilyl-α-D-arabinofuranoside 
• 1236193-28-4 methyl 5-O-benzoyl-3-O-benzyl-α-D-arabinofuranoside 
• 440359-29-5 methyl 2,5-bis-O-di-tert-butylsilyl-3-C-hydroxymethyl-6-O-(4-toluene)sulfonyl-α-D-arabinofuranoside 
• 440359-31-9 methyl 5-O-tert-butyldimethylsilyl-3-C-hydroxymethyl-6-O-(4-toluene)sulfonyl-α-D-arabinofuranoside 
• 1053626-56-4 Benzoic acid (2R,3S,4S,5S)-3-bromomethyl-2-(tert-butyl-dimethyl-silanyloxymethyl)-4-hydroxy-5-methoxy-tetrahydro-furan-3-yl ester 
• 440359-33-1 methyl 3,6-di-O-(benzylidene acetal)-2,5-bis-O-tert-butylsilyl-3-C-hydroxymethyl-α-D-arabinofuranoside 
• 440359-35-3 methyl 3,6-di-O-(benzylidene acetal)-5-O-tert-butyldimethylsilyl-3-C-hydroxymethyl-α-D-arabinofuranoside 
• 440359-36-4 methyl 2,6-anhydro-3-O-benzoyl-5-O-tert-butyldimethylsilyl-3-C-hydroxymethyl-α-D-arabinofuranoside 
• 440359-30-8 Toluene-4-sulfonic acid (2R,3S,4S,5S)-3,4-dihydroxy-2-hydroxymethyl-5-methoxy-tetrahydro-furan-3-ylmethyl ester 
• 440359-38-6 methyl 2,6-anhydro-5-O-benzoyl-3-C-hydroxymethyl-α-D-arabinofuranoside 
• 440359-34-2 methyl 3,6-di-O-(benzylidene acetal)-3-C-hydroxymethyl-α-D-arabinofuranoside 

Relevant academic research and scientific papers

Probing the effect of acylation on arabinofuranose ring conformation in di- and trisaccharide fragments of mycobacterial arabinogalactan

(Figure presented) A major component of the cell wall of mycobacteria is the mycolyl-arabinogalactan (mAG) complex. The arabinose and galactose residues in mAG are found solely in the furanose form, and it has been suggested that the flexibility of these five-membered rings allows for the tight packing of mycolic acids. In order to probe the flexible scaffold hypothesis , we designed and synthesized glycolipids 3-6 and 8-11 as simple models of the terminal portion of mAG. A set of donors and acceptors were explored for preparing the key β-(1→2) linkage in 2-6, and the best selectivity and yield can be obtained by using the electron-rich thioglycoside donor 14 and the O-5 p-methoxybenzyl-protected acceptor 17. Both α-linkages in the trisaccharides 7-11 were formed in a one-pot reaction. The conformations of compounds 2-11 were studied using solution-state NMR spectroscopy, but little change was observed in the coupling constants for the ring protons between 2 and 3-6 or between 7 and 8-11. However, the rotamer populations about the C-4-C-5 bond for the β-linked ring in disaccharide 2 did change upon acylation at O-5.

Oligofuranosides containing conformationally restricted residues: Synthesis and conformational analysis

The synthesis of a panel of arabinofuranosyl oligosaccharide analogues (5-13) in which one ring is locked into either the E3 or oE conformation is described. The E3-locked scaffolds 15 and 16 required for the synthesis of 5-10 were prepared in one step from known 1,5-anhydroalditols. A number of routes were explored for the preparation of the oE-locked monosaccharide derivative 17 needed for the preparation of 11-13. The successful synthesis of 17 was achieved in 17 steps from D-arabinose. Subsequent analysis of 5-13 by 1H NMR spectroscopy demonstrated that the locked residue does not exert any detectable influence upon the conformers populated by adjacent conformationally unrestricted furanose rings.