Stereoselective synthesis of aryl 1,2- cis -furanosides and its application to the synthesis of the carbohydrate portion of antibiotic hygromycin A

Xu, Yuan; Bin, Huachao; Su, Fenghua; Yang, Jinsong

doi:10.1016/j.tetlet.2017.02.079

Cited by 11 publications

(1 citation statement)

References 29 publications

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“…Recently, a facile hydrogen-bond-mediated aglycone delivery (HAD) approach was uncovered by Demchenko and co-workers to synthesize stereoselectively various challenging 1,2- cis -pyranosides . Relying on such a concept, our group developed a novel 2-quinolinecarbonyl (Quin)-assisted 1,2- cis -furanosylation method for efficient preparation of β-arabino- and α-galactofuranosides . The Quin group, serving as a hydrogen bond acceptor, shows a strong stereocontrolling ability in the condensation of furanosyl thioglycoside donors with a wide range of carbohydrate and noncarbohydrate alcohols.…”

Section: Introductionmentioning

confidence: 99%

Stereodirecting Effect of C5-Carboxylate Substituents on the Glycosylation Stereochemistry of 3-Deoxy-d-manno-oct-2-ulosonic Acid (Kdo) Thioglycoside Donors: Stereoselective Synthesis of α- and β-Kdo Glycosides

et al. 2018

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The stereodirecting effect of C5-ester functions on the glycosylation stereoselectivity of 3-deoxy-d- manno-oct-2-ulosonic acid (Kdo) ethyl thioglycoside donors is presented. The coupling of 5- O-arylcarbonyl or acetyl protected Kdo thioglycosides with acceptors proceeds in an α-selective and high-yielding manner, leading to formation of α-linked Kdo glycosides products. On the other hand, the glycosylation stereoselectivity of the 5- O-2-quinolinecarbonyl (Quin) or 4-nitropicoloyl substituted Kdo thioglycoside donors is switchable: (1) The glycosylation of the 5- O-Quin carrying Kdo donors with primary glycosyl acceptors shows complete β-stereoselectivity, furnishing the corresponding β-glycosides in good-to-excellent yield. (2) The stereochemical outcome of the secondary acceptors with these Kdo donors is determined mainly by the stereoelectronic nature of the acceptor. Only or predominant α anomeric products are obtained when the Kdo donors couple with the disarmed or highly crowded secondary carbohydrate acceptors, while the selectivity may switch to predominant β in the glycosylation of the 5- O-4-nitropicoloyl carrying donor with more reactive secondary alcohols. The synthetic use of the newly developed Kdo donors 1c and 7b has been demonstrated by facile preparation of a structurally unique trisaccharide motif 19 which possesses both α- and β-Kdo glycosidic bonds.

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Section: Introductionmentioning

confidence: 99%

Stereodirecting Effect of C5-Carboxylate Substituents on the Glycosylation Stereochemistry of 3-Deoxy-d-manno-oct-2-ulosonic Acid (Kdo) Thioglycoside Donors: Stereoselective Synthesis of α- and β-Kdo Glycosides

et al. 2018

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Stereoselective Synthesis of a Tetrasaccharide Fragment from Cellulosome Produced by Clostridium thermocellum

Zeng

Yang

2020

Asian J Org Chem

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An efficient synthesis of a structurally congested tetrasaccharide portion from the cellulosome produced by Clostridium thermocellum has been accomplished through a stepwise glycosylation strategy. The key steps for the synthesis include the stereocontrolled construction of a range of challenging 1,2‐cis glycosidic linkages. The 5‐O‐(2‐quinolinecarbonyl) substituted D‐galactofuranosyl thioglycoside 2, 4,6‐O‐benzylidene protected 2‐azido‐2‐deoxyglucose thioglycoside 3 c, and 4,6‐O‐benzylidene protected D‐galactopyranosyl thioglycoside 4 were employed as glycosyl donors, respectively, for the high‐yielding and stereoselective formation of the corresponding 1,2‐cis‐α‐Galf, α‐GlcNAc, and α‐Galp linkages.

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Stereoselective Synthesis of a Tetrasaccharide Fragment from Rhamnogalacturonan II Side Chain A

et al. 2022

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An efficient synthesis of a complex tetrasaccharide fragment 1 structurally related to rhamnogalacturonan II side chain A has been accomplished through a stepwise glycosylation strategy. Challenges involved in the synthesis include the facile construction of the sterically crowded L-fucopyranose core and the stereoselective formation of two 1,2-cis-glycosidic linkages. The 3,4-disubstituted L-fucopyranoside structure was successfully constructed through a 'counterclockwise' glycosylation sequence, namely, the less reactive axial 4-OH group of the central fucose unit was glycosylated first, then the 3-OH. Besides, a 2-pyridinecarbonyl-assisted α-D-xylosylation was developed to synthesize the α-D-xylopyranosidic linkage and a 3,4-O-benzoyl-controlled α-L-galactosylation reaction was used for the stereoselective synthesis of the corresponding α-L-galactopyranosidic linkage.

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Stereoselective synthesis of aryl 1,2- cis -furanosides and its application to the synthesis of the carbohydrate portion of antibiotic hygromycin A

Cited by 11 publications

References 29 publications

Stereodirecting Effect of C5-Carboxylate Substituents on the Glycosylation Stereochemistry of 3-Deoxy-d-manno-oct-2-ulosonic Acid (Kdo) Thioglycoside Donors: Stereoselective Synthesis of α- and β-Kdo Glycosides

Stereodirecting Effect of C5-Carboxylate Substituents on the Glycosylation Stereochemistry of 3-Deoxy-d-manno-oct-2-ulosonic Acid (Kdo) Thioglycoside Donors: Stereoselective Synthesis of α- and β-Kdo Glycosides

Stereoselective Synthesis of a Tetrasaccharide Fragment from Cellulosome Produced by Clostridium thermocellum

Stereoselective Synthesis of a Tetrasaccharide Fragment from Rhamnogalacturonan II Side Chain A

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