Acid zeolites as efficient catalysts for O- and S-glycosylation

Rauter, Amélia P.; Almeida, Tânia Santos de; Xavier, Nuno M.; Siopa, Filipa; Vicente, Ana I.; Lucas, Susana D.; Marques, João Pedro; Ribeiro, F. Ramôa; Guisnet, M.; Ferreira, Maria João

doi:10.1016/j.molcata.2007.06.002

Cited by 20 publications

(9 citation statements)

References 41 publications

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“…Porous acidic zeolites (ZSM-5, Beta Y, HY) also limits the formation of oligomeric products, possibly due to their small pore sizes. [150][151][152][153][154] Yields of butyl D-glucosides up to 98% have been reported at moderate temperatures (<110 °C). Brønsted acidity, Si/Al ratio, pore and crystallite size of zeolites are the main factors which control the conversion and product selectivity of this process.…”

Section: Glycosylation Of Sugarsmentioning

confidence: 99%

Chemical conversion pathways for carbohydrates

2015

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Section: Glycosylation Of Sugarsmentioning

confidence: 99%

Chemical conversion pathways for carbohydrates

2015

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“…In particular, more efficient and generalizable methods for the synthesis of furanose glycosylating agents are highly desirable. In addition almost no work investigating the synthesis of furanosides possessing an acetamide at C2 (i.e., N-acetylgalactofuranoside or N-acetylglucofuranoside moieties) has been carried out (104,105), although such species are found in bacterial glycans (106). This area thus remains a challenge for the future.…”

Section: H Conclusionmentioning

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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“…26 Again, selective synthesis of both per-Oacetylated furanose remains a challenging task, in particular for Galf NAc, as the only published procedure generated a mixture of Galf NAc and GalpNAc. 27 Thus, the silylation/acetylation procedure was applied to D-GalA and D-GalNAc (Scheme 2).…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…Physico-chemical properties and spectroscopic data are consistent with the described compound. 27 ■ ASSOCIATED CONTENT * S Supporting Information 1 H and 13 …”

Section: ■ Experimental Sectionmentioning

confidence: 99%

Two-Step Synthesis of Per-O-acetylfuranoses: Optimization and Rationalization

et al. 2012

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A simple two-step procedure yielding peracetylated furanoses directly from free aldoses was implemented. Key steps of the method are (i) highly selective formation of per-O-(tert-butyldimethylsilyl)furanoses and (ii) their clean conversion into acetyl ones without isomerization. This approach was easily applied to galactose and structurally related carbohydrates such as arabinose, fucose, methyl galacturonate and N-acetylgalactosamine to give the corresponding peracetylated targets. The success of this procedure relied on the control of at least three parameters: (i) the tautomeric equilibrium of the starting unprotected oses, (ii) the steric hindrance of both targeted furanoses and silylating agent, and finally, (iii) the reactivity of each soft nucleophile during the protecting group interconversion.

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Acid zeolites as efficient catalysts for O- and S-glycosylation

Cited by 20 publications

References 41 publications

Chemical conversion pathways for carbohydrates

Chemical conversion pathways for carbohydrates

Chemical Synthesis of Furanose Glycosides

Two-Step Synthesis of Per-O-acetylfuranoses: Optimization and Rationalization

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