2018
DOI: 10.1039/c7cc09260a
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Iridium catalysis: reductive conversion of glucan to xylan

Abstract: By using iridium catalysed dehydrogenative decarbonylation, we converted a partly protected cellobioside into a fully protected xylobioside. We demonstrate good yields with two different aromatic ester protecting groups. The resulting xylobioside was directly used as glycosyl donor in further synthesis of a xylooctaose.

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Cited by 6 publications
(6 citation statements)
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“…Syntheses of homologues of xylose higher than xylotriose have rarely been pursued [28,29,30] . We envisaged that the five‐unit β‐1→4‐xylooligomer could be accessed through union of the Xyl 2 acceptor 37 and the Xyl 3 donor 38 (Figure 5D).…”
Section: Resultsmentioning
confidence: 99%
See 1 more Smart Citation
“…Syntheses of homologues of xylose higher than xylotriose have rarely been pursued [28,29,30] . We envisaged that the five‐unit β‐1→4‐xylooligomer could be accessed through union of the Xyl 2 acceptor 37 and the Xyl 3 donor 38 (Figure 5D).…”
Section: Resultsmentioning
confidence: 99%
“…Syntheses of homologues of xylose higher than xylotriose have rarely been pursued. [28,29,30] We envisaged that the five-unit β-1!4-xylooligomer could be accessed through union of the Xyl 2 acceptor 37 and the Xyl 3 donor 38 (Figure 5D). Conversion of tolyl-1-thio-β-xylobioside (35) to the acceptor 37 was achieved via a selective protection of the C-4'À OH as the p-nitrobenzoyl ester followed by pivaloyl protection of the remaining hydroxyl groups to give polyester 36 (Figure 5A).…”
Section: Preparation Of Undecasulfoà Xylopentaose (Xyl 5 à So 3 )mentioning
confidence: 99%
“…Complexes 13 and 14 were separated by chromatography on silica gel and fully characterized (see the Experimental Section and the Supporting Information for details). It is worth mentioning that the dehydrogenative decarbonylation of alcohols is a synthetically valuable transformation, efficiently performed with complexes of platinum group metals. , Although different types of alcohols have been tested in these reactions (more frequently primary aliphatic and benzylic), sugars have been rarely employed as substrates and, to the best of our knowledge, these processes have never been reported for nucleosides.…”
Section: Resultsmentioning
confidence: 99%
“…In one case, two arabinoses were glycosylated onto the 2 and 3 positions of the same xylose residue although a very low yield was obtained illustrating the challenge of producing more densely substituted arabinoxylans. Linear xylans, on the other hand, where no additional substituents are present, are more readily assembled by either stepwise or blockwise approaches and so far linear xylans up to decaxylans have been prepared, which includes an approach by cleaving the hydroxymethyl group of glucans and the assembly of S -linked oligoxylans …”
Section: Introductionmentioning
confidence: 99%