Janus glycosides of next generation: Synthesis of 4-(3-chloropropoxy)phenyl and 4-(3-azidopropoxy)phenyl glycosides

Stepanova, Elena V.; Abronina, Polina I.; Zinin, Alexander I.; Chizhov, Alexander O.; Kononov, L. O.

doi:10.1016/j.carres.2018.11.013

Cited by 16 publications

(18 citation statements)

References 65 publications

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“…Retrosynthetic analysis (Scheme ) of branched protected tetrasaccharide fragment (block A ) of polysaccharides from A. brasilense sp7, which include 1,2‐ cis ‐fucosyl linkage, is based on the use of benzyl‐free approach that we have been developing for some time . The building blocks were designed as Janus glycosides, with CEP aglycon. O ‐Silyl and O ‐acyl (acetyl or benzoyl) protective groups were used at other positions.…”

Section: Resultsmentioning

confidence: 99%

“…After deprotection of the obtained tetrasaccharide 28 with CEP aglycon that can easily be transformed to AEP aglycon, both of which belong to the class of Janus aglycons (possessing both protective and pre‐spacer features),, and conversion to neoglycoconjugates using click‐chemistry or by transformation to the corresponding amino derivative, the role of lipopolysaccharide of rhizobacterium A. brasilense sp7 in plant–microbe symbiosis will be studied. The intermediate protected oligosaccharides with cleavable pre‐spacer CEP aglycon will be further used in the synthesis of more complex oligosaccharide fragments of rhizobacterium A. brasilense sp7.…”

Section: Resultsmentioning

confidence: 99%

“…Recently, we have employed both the protective and the pre‐spacer features of 4‐(2‐chloroethoxy)phenyl (CEP) and 4‐(2‐azidoethoxy)phenyl (AEP) Janus aglycons, in the synthesis of tetrasaccharide fragment 1 of polysaccharides from A. brasilense sp7 (Figure ) . The presence of AEP spacer aglycon allows straightforward preparation of neoglycoconjugates, which will be used for the study of the role of lipopolysaccharide of A. brasilense sp7 in plant–microbe symbiosis and will enable identification and characterization of biomacromolecules of plant and bacterial cells, which are responsible for the success of interactions of the organisms .…”

Section: Introductionmentioning

confidence: 99%

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Unusual Outcome of Glycosylation: Hydrogen‐Bond Mediated Control of Stereoselectivity by N‐Trifluoroacetyl Group?

et al. 2020

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During the synthesis of protected tetrasaccharide fragment of the repeating unit of polysaccharide of Azospirillum brasilense sp7 we found that glycosylation with a mixture of protected N‐trifluoroacetyl (TFA)‐protected glucosamine N‐phenyltrifluoroacetimidate and the corresponding 2‐trifluoromethyl‐oxazoline led to 1,2‐cis‐linked glycoside along with the expected 1,2‐trans‐linked isomer. This fact looks quite unusual bearing in mind that both N‐TFA‐containing glycosyl donor and 2‐trifluoromethyl‐oxazoline are usually expected to favor the formation of 1,2‐trans‐glycosides. Formation of 1,2‐cis‐glycoside was explained by hydrogen‐bond mediated complexation of hydrogen atom of NHTFA at C‐2 of oxacarbenium ion derived from glycosyl donor and oxygen atom of hydroxy group of the incoming nucleophile. Conversely, glycosylations with N‐phthaloyl protected glycosyl donors resulted in exclusive formation of 1,2‐trans‐isomer presumably due to a significant steric effect and the absence of additional hydrogen‐bonding sites of N‐phthaloyl group.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Unusual Outcome of Glycosylation: Hydrogen‐Bond Mediated Control of Stereoselectivity by N‐Trifluoroacetyl Group?

et al. 2020

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“…2 Other examples include the galactan of Actinobacillus pleuropneumoniae 3 and the galactan of Bifidobacterium catenulatum 4 . Since only few methods to access furanose building blocks have been reported, 5 the search for efficient and reliable methods for the synthesis of selectively functionalized O-furanosides is an important area of current research.…”

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confidence: 99%

“…Starting from the known benzyl 4,6-O-benzylidene--Dgalactopyranoside (4) 9 we synthesized benzyl 4,6-Obenzylidene-2,3-bis-O-(triisopropylsilyl)--D-galactopyranoside (5). The cleavage of 4,6-O-benzylidene group in the obtained Oglycoside 5 with aq TFA in CH2Cl2 (method A) gave the corresponding benzyl -D-galactopyranoside 6 in 75% yield (Scheme 2).…”

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confidence: 99%

Trifluoroacetic Acid Promoted Ring Contraction in 2,3-Di-O-silylated O-Galactopyranosides and Hemiacetals

Abronina¹,

Malysheva²,

Zinin³

et al. 2022

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A pyranose ring contraction of 2,3-di-O-silylated O-galactopyranosides with retention of aglycone promoted by anhydrous trifluoroacetyc acid (TFA) in CH2Cl2 was demonstrated for the first time. In addition, TFA-promoted pyranose ring contraction of 2,3-bis-O-(triisopropylsilyl)-D-galactopyranose with formation of the corresponding anomeric triols in furanose form was successfully performed. A representative series of β-D-galactopyranosides with Me, Bn, allyl, or 3-(trifluoroacetamido)propyl aglycones has been investigated. TBDPS protective groups were found to be more stable than TIPS groups under conditions of TFA-promoted pyranose ring contraction. An easy access to 2,3-di-O-TBDPS substituted allyl and benzyl galactofuranosides and 2,3-bis-O-(triisopropylsilyl)-β-D-galactofuranose may present an advantage in synthesis of selectively protected monosacharide bilding blocks, useful for the synthesis of biologically important oligosaccharides.

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Sweetened Alkylated Verdazyls Effectively Kill Cancer Cells under Light Irradiation

et al. 2023

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The development of novel photo‐dynamic therapy (PDT) agents enabling to treat the oxygen‐deficient tumors is the emerging tasks for the modern medicinal chemistry. Herein, we describe the design and preparation of water‐soluble agents for PDT which generate active radical species upon light irradiation. Two conjugates of carbohydrates with 1,2,4,6‐substituted‐1,4‐dihydro‐1,2,4,5‐tetrazin‐3(2H)‐ones (AlkVZs) demonstrated high oxygen‐independent cytotoxicity on PC‐3 and Jurkat cancer cells under light irradiation combining with low toxicity in the dark. The efficacy of prepared compounds was estimated using MTT and Alamar Blue tests as well as microscopic dead/live colored images and flow cytometry. The analysis of obtained results reveals the influence of sugar moiety on the activity of AlkVZs. We believe that obtained compounds have high potency as platform for design of new agents for photo‐dynamic therapy.

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Janus glycosides of next generation: Synthesis of 4-(3-chloropropoxy)phenyl and 4-(3-azidopropoxy)phenyl glycosides

Cited by 16 publications

References 65 publications

Unusual Outcome of Glycosylation: Hydrogen‐Bond Mediated Control of Stereoselectivity by N‐Trifluoroacetyl Group?

Unusual Outcome of Glycosylation: Hydrogen‐Bond Mediated Control of Stereoselectivity by N‐Trifluoroacetyl Group?

Trifluoroacetic Acid Promoted Ring Contraction in 2,3-Di-O-silylated O-Galactopyranosides and Hemiacetals

Sweetened Alkylated Verdazyls Effectively Kill Cancer Cells under Light Irradiation

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