Chemical Synthesis Elucidates the Key Antigenic Epitope of the Autism‐Related Bacterium <i>Clostridium bolteae</i> Capsular Octadecasaccharide

Cai, Juntao; Hu, Jing; Qin, Chunjun; Li, Lingxin; Shen, Dacheng; Tian, Guangzong; Zou, Xiang; Seeberger, Peter H.; Yin, Jian

doi:10.1002/ange.202007209

Cited by 3 publications

(1 citation statement)

References 113 publications

(70 reference statements)

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“…Compound 43 was firstly converted into iodide 44a and bromide 44b , respectively, using 2,2′-azobis(2-methylpropionitrile) (AIBN) and a suitable hydrogen source as reductant and transfer agent. Unfortunately, neither reduction of 44a with tributyltin hydride (HSnBu 3 ) 17 nor 44b with tris(trimethylsilyl)silane (TTMS) 18 gave an acceptable yield of 3 . Next, by converting 43 into xanthate 44c 19 and then reducing the intermediate with TTMS, the yield of 3 was elevated to 55%.…”

Section: Table 1 Reduction Conditions For Conversion Of...mentioning

confidence: 99%

Scalable, Stereocontrolled, Total Synthesis of Carolacton

Bian

Yang

et al. 2023

Synthesis

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A route for the scalable, stereocontrolled, total synthese of carolacton is presented starting from commercially available S-Roche ester, D-Ribose, and known allylic alcohol 11. Key transformation in the total synthesis included a [3,3]-Claisen rearrangement, Sharpless asymmetric epoxidation–methyl ring-opening, or Leighton asymmetric crotylation, Evans-aldol–reductive deoxygenation, and ring closing metathesis (RCM). The total synthesis of carolacton (151 mg isolated, 9.2% overall yield) was completed in 23 linear steps starting from 11. Additionally, 56mg of the carolacton C15–C16 cis-olefin isomer were obtained.

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Section: Table 1 Reduction Conditions For Conversion Of...mentioning

confidence: 99%

Scalable, Stereocontrolled, Total Synthesis of Carolacton

Bian

Yang

et al. 2023

Synthesis

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Direct Synthesis of 2,6‐Dideoxy‐β‐glycosides and β‐Rhamnosides with a Stereodirecting 2‐(Diphenylphosphinoyl)acetyl Group

et al. 2022

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Anomeric stereocontrol is usually one of the major issues in the synthesis of complex carbohydrates, particularly those involving β-configured 2,6-dideoxyglycoside and D/L-rhamnoside moieties. Herein, we report that 2-(diphenylphosphinoyl)acetyl is highly effective as a remote stereodirecting group in the direct synthesis of these challenging β-glycosides under mild conditions. A deoxy-trisaccharide as a mimic of the sugar chain of landomycin E was prepared stereospecifically in high yield. The synthetic potential was also highlighted in the synthesis of Citrobacter freundii O-antigens composed of a!] repeating unit, wherein the convergent assembly up to a nonasaccharide was realized with a strongly βdirecting trisaccharide donor. Variable-temperature NMR studies indicate the presence of intermolecular Hbonding between the donor and the bulky acceptor as direct spectral evidence in support of the concept of hydrogen-bond-mediated aglycone delivery.

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Direct Synthesis of 2,6‐Dideoxy‐β‐glycosides and β‐Rhamnosides with a Stereodirecting 2‐(Diphenylphosphinoyl)acetyl Group

et al. 2022

View full text Add to dashboard Cite

Anomeric stereocontrol is usually one of the major issues in the synthesis of complex carbohydrates, particularly those involving β‐configured 2,6‐dideoxyglycoside and d/l‐rhamnoside moieties. Herein, we report that 2‐(diphenylphosphinoyl)acetyl is highly effective as a remote stereodirecting group in the direct synthesis of these challenging β‐glycosides under mild conditions. A deoxy‐trisaccharide as a mimic of the sugar chain of landomycin E was prepared stereospecifically in high yield. The synthetic potential was also highlighted in the synthesis of Citrobacter freundii O‐antigens composed of a [→4)‐α‐d‐Manp‐(1→3)‐β‐d‐Rhap(1→4)‐β‐d‐Rhap‐(1→] repeating unit, wherein the convergent assembly up to a nonasaccharide was realized with a strongly β‐directing trisaccharide donor. Variable‐temperature NMR studies indicate the presence of intermolecular H‐bonding between the donor and the bulky acceptor as direct spectral evidence in support of the concept of hydrogen‐bond‐mediated aglycone delivery.

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Chemical Synthesis Elucidates the Key Antigenic Epitope of the Autism‐Related Bacterium Clostridium bolteae Capsular Octadecasaccharide

Cited by 3 publications

References 113 publications

Scalable, Stereocontrolled, Total Synthesis of Carolacton

Scalable, Stereocontrolled, Total Synthesis of Carolacton

Direct Synthesis of 2,6‐Dideoxy‐β‐glycosides and β‐Rhamnosides with a Stereodirecting 2‐(Diphenylphosphinoyl)acetyl Group

Direct Synthesis of 2,6‐Dideoxy‐β‐glycosides and β‐Rhamnosides with a Stereodirecting 2‐(Diphenylphosphinoyl)acetyl Group

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