Syntheses of 1‐thio‐<scp>D</scp>‐xylose and <scp>D</scp>‐ribose esters of diorganoarsinous acids and their anticancer activity

Gao, Mingzhang; Chen, Yiwen; Tan, Sisi; Reibenspies, Joseph H.; Zingaro, Ralph A.

doi:10.1002/hc.20388

Cited by 16 publications

(10 citation statements)

References 20 publications

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“…The synthesis of the O-disaccharide acceptor 4 starts with benzoylation of diol 26, which was prepared following literature procedures (Scheme 11). [43][44][45][46] The anomeric thioacetal of 5 was hydrolyzed and benzoylation afforded compound 27 in 70% yield [47] . The 4-position was deprotected with DDQ to provide acceptor 28 in 74% yield.…”

Section: Resultsmentioning

confidence: 99%

Convergent strategy for the synthesis of S-linked oligoxylans

Bonora

Boos

Clausen

2017

Carbohydrate Research

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Arabinoxylans (AX) are a major class of hemicellulose and an important polysaccharide component of lignocellulosic biomass. To utilize the glycan polymer effectively, it is desirable to learn more about the enzymatic hydrolysis of AXs. Well-defined glycans can help to elucidate these processes. Here, we report the efficient synthesis of a mixed O- and S-linked tetraxylan. This thio-oligosaccharide has been developed as a putative inhibitor of arabinoxylan degrading enzymes used for the saccharification of biomass. Two common approaches for the synthesis of thio-oligosaccharides, either involving 1-thioglycoside donors or thioacceptors, are presented and compared regarding byproduct formation and yields. Both methods have shown to be useful for the synthesis of thiolinkages in oligoxylans assembly. However, the success of the reaction is highly dependent on the "match" between donors and acceptors.

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Section: Resultsmentioning

confidence: 99%

Convergent strategy for the synthesis of S-linked oligoxylans

Bonora

Boos

Clausen

2017

Carbohydrate Research

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“…In the synthesis of thiol derivatives of the glycol chain, 1,2,3,4-tetra-o-acetyl-D-xylopyranose is firstly synthesized. The product 1 can be obtained by using D-xylose and Acetic anhydride for the amide reaction [ 45 ]. The product 1, triethylene glycol and boron trifluoride diethyl etherate react to synthesize the product T1.…”

Section: Methodsmentioning

confidence: 99%

Synthesis and cytotoxic analysis of thiolated xylose derivatives decorated on gold nanoparticles

Shiue

Chen

Chang

et al. 2020

Biotechnology Reports

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“…(Hetero)aryl halides are commercially available. Thiosaccharides 1a–f 21–23 were synthesized as according to literature protocols.…”

Section: Methodsmentioning

confidence: 99%

“…Compound 1f: 23 This substrate is not enough stable for its characterization and was used immediately after its preparation.…”

Section: Methodsmentioning

confidence: 99%

Palladium‐Catalyzed Cross‐Coupling Reaction of Thioglycosides with (Hetero)aryl Halides

Brachet¹,

Brion²,

Messaoudi³

et al. 2013

Adv Synth Catal

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a-and b-thioglycosides serve as effective nucleophiles for Buchwald-Hartwig cross-coupling reactions using functionalized (hetero)aryl halides. The functional group tolerance on the electrophilic partner is typically high, both benzyl and acetate protecting groups on the carbohydrate are tolerated, and anomer selectivities of thioglycosides are high in all cases studied. The efficiency of this general protocol was well demonstrated by the synthesis of 4methyl-7-thioumbelliferyl-b-d-cellobioside (MUS-CB).

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Syntheses of 1‐thio‐D‐xylose and D‐ribose esters of diorganoarsinous acids and their anticancer activity

Abstract: Several thio-D-xylose and

Cited by 16 publications

References 20 publications

Convergent strategy for the synthesis of S-linked oligoxylans

Convergent strategy for the synthesis of S-linked oligoxylans

Synthesis and cytotoxic analysis of thiolated xylose derivatives decorated on gold nanoparticles

Palladium‐Catalyzed Cross‐Coupling Reaction of Thioglycosides with (Hetero)aryl Halides

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