1268604-13-2

Upstream product

• 532-20-7 D-arabinofuranose 
• 19139-80-1 ((3aS,5R,6R,6aS)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methanol 
• 1268604-23-4 p-tolyl 2-O-acetyl-3,5-di-O-benzyl-1-thio-α-D-arabinofuranoside 

Downstream Products

• 1268604-12-1 2,3-di-O-benzyl-β-D-arabinofuranosyl-(1f2)-3,5-di-O-benzyl-α-D-arabinofuranosyl-(1->5)-3-O-benzyl-1,2-O-isopropylidene-β-D-arabinofuranose 

Relevant academic research and scientific papers

Synthetic and Immunological Studies of Mycobacterial Lipoarabinomannan Oligosaccharides and Their Protein Conjugates

Lipoarabinomannan (LAM) is one of the major constituents of the Mycobacterium tuberculosis cell wall and an attractive molecular scaffold for antituberculosis drug and vaccine development. In this paper, a convergent strategy was developed for the synthes

Synthesis of docosasaccharide arabinan motif of mycobacterial cell wall

Mycobacterial arabinan is a common constituent of both arabinogalactan (AG) and lipoarabinomannan (LAM). In this study, synthesis of β-Araf containing common arabinan docosasaccharide motif (22 Araf monomer units) of mycobacterial cell wall was achieved. Our synthetic strategy toward arabinan involves (1) the stereoselective β-arabinofuranosylation using both 3,5-O-TIPDS-protected and NAP-protected arabinofuranosyl donors for straightforward intermolecular glycosylation and intramolecular aglycon delivery (IAD), respectively, and (2) the convergent fragment coupling with branched fragments at the linear sequence using thioglycoside donor obtained from the corresponding acetonide at the reducing terminal of each fragment through a three-step procedure. Because the acetonide at the reducing terminal of all fragments would be converted to thioglycoside as the glycosyl donor, and mainly Bn ether protections were used, our strategy will be readily applicable to the synthesis of more complex arabinan, arabinogalactan, and arabinomycolate derived from mycobacterial CWS.