1,2,5-ortho esters of d-arabinose as versatile arabinofuranosidic building blocks. Concise synthesis of the tetrasaccharidic cap of the lipoarabinomannan of Mycobacterium tuberculosis

Bamhaoud, Toufiq; Sanchez, Sylvie; Prandi, Jacques

doi:10.1039/b000873g

Cited by 65 publications

(27 citation statements)

References 26 publications

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“…The versatile precursor trisaccharide 1 7b and donor fragments 2 , 19 3 , 20 4 and 5 21 were prepared as previously reported (ESI † ). Using these building blocks, the synthesis of the 8 core structures were performed in a convergent strategy (Scheme 1).…”

Section: Resultsmentioning

confidence: 99%

Efficient chemoenzymatic synthesis of an N-glycan isomer library

et al. 2015

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Section: Resultsmentioning

confidence: 99%

Efficient chemoenzymatic synthesis of an N-glycan isomer library

et al. 2015

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“…Furthermore, furansoyl bromides such as 8, when protected with acyl protecting groups, are useful intermediates for the formation of orthoesters 11 and 12. The former have been used as glycosylating agents (28,29) while the latter have found utility in the preparation of differentially-protected furanose derivatives (30)(31)(32)(33). Other reports describe the synthesis of n-pentenyl glycoside donors directly via Fischer glycosylation with n-pentenol (18,20).…”

Section: B Methods For Obtaining Furanose Glycosyl Donorsmentioning

confidence: 99%

“…In one example (30), coupling of 62 and trisaccharide diol 63 led to a 23% overall yield of pentasaccharide 64, a fragment of mycobacterial AG containing two β-D-arabinofuranose residues. The Prandi group has used this approach to synthesize other β-Darabinofuranosides of mycobacterial origin (31,86). More recent work from the Ito group has explored the use of donors functionalized with a napthylmethyl ether at O2 in the synthesis of β-arabinofuranosides by IAD (87).…”

Section: F Use Of Conformationally-flexible Donorsmentioning

confidence: 99%

Chemical Synthesis of Furanose Glycosides

Imamura

Lowary

2011

TIGG

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Many bacterial, fungal, parasitical and plant species produce glycans containing O-furanoside linkages. These glycoconjugates are often essential for the viability of the organisms that produce them, and an increasing amount of work focused on their chemical synthesis has been carried out in recent years. However, despite these advances, compared to the synthesis of pyranose glycosides, this area has been poorly investigated. In this review we highlight the challenges inherent in the synthesis of furanose glycosides, summarize achievements in the field and suggest directions for future work.

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“…Although several reports have described organic syntheses of galactofuranose-based compounds, generally speaking, the chemical synthesis of oligosaccharides remains a challenge. 13,[16][17][18][19][20][21] This is because appropriate, reactive and anomerically-pure monomers must first be prepared and then linked together in a stereo-and regiospecific fashion via glycosidic bonds. Increasingly, to simplify some or all of the synthetic steps for the production of oligosaccharides, enzymatic or chemoenzymatic strategies are being adopted.…”

Section: Introductionmentioning

confidence: 99%