Emerging Trends in Glycoscience, Part #1: Exploiting the fluorine-directing effect to access rare L-hexoses - presented by Professor Vito Ferro and Professor Vinod Kumar Tiwari FRSC | Synthesis and immunological evaluation of oligosaccharide-protein conjugates for the development of a vaccine candidate against avian pathogenic Escherichia coli O1 - presented by Professor Daisuke Takahashi

Emerging Trends in Glycoscience, Part #1

Professor Daisuke TakahashiProfessor Vito Ferro
Slide at 16:39
Syn thesis
Tris(pentafluorophenyl)borane-Catalyzed Stereoselective C-Glycosyl-
Paper
Synthesis 2024, 56. 1026-1034
ation of Glycals: A Facile Synthesis of Allyl and Alkynyl Glycosides
1026
DOI: 10.1055/a-2186-7116
A. Gaurav
B(C6F5)3 Catalyzed stereoselective synthesis of 2,3-unsaturated C-glycosides
Z. Azeem
P. K. Mandal
CSIR-Central Drug Research In-
stitute, India
Allyl glycosides
B(C6F5)3
Glucal, Galactal, Rhamnal,
disaccharide glycal
Alkynyl glycosides
Syn thesis
Chemoenzymatic Synthesis of arabino-Configured Bicyclic Nucleosides
Paper
Synthesis 2024, 56, 1035-1041
1035
DOI: 10.1055/s-0041-1738440
H. Singla
J. Malty
S. Kumar
Lipozyme-TL IM
K. Kavita
R. Chaudhary
OBn OAc
Vinyl acetate
OBn OH
acetonitrile
OBn OH
A. K. Prasad*
99 and 97%
University of Delhi, India
Overall Yields: 24 and 27%
R=H, CH3
Thieme Live Cheminar on 'Emerging Trends in Glycoscience, Part #1'
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References
  • 1.
    P. K. Mandal et al. (2023) Tris(pentafluorophenyl)borane-Catalyzed Stereoselective C-Glycosylation of Glycals: A Facile Synthesis of Allyl and Alkynyl Glycosides. Synthesis
  • 2.
    A. K. Prasad et al. (2023) Chemoenzymatic Synthesis of arabino-Configured Bicyclic Nucleosides. Synthesis
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Summary (AI generated)

The methods are very appealing for application in the industry. One notable group from the CIF, led by Doctor Pinto Mandal, reported a stereoselective α C glycosylation schedule for a variety of glycols using trimethyl and propargyl phenyl acetylene via simultaneous bora activation of the glycosyl donor using pre-pentafluoroborate. The desired compounds were isolated in high yield with excellent α selectivity.

Another significant work comes from the late Professor A. K. Prasad from the University of Delhi. This paper was submitted on February 7, 2023. Unfortunately, on February 8, we received the sad news that he had passed away. His paper marked the last of his career. Professor Rao Prasad and his group developed a chemoenzymatic synthesis of arabino-configured bicyclic nucleosides. The biological significance of nucleosides, the building blocks for nucleic acids, can be tailored by chemically modifying the C-5 carbon sugars to influence its sugar puckering. Additionally, this group established a chemotic convergent route to the high-yielding synthesis of bicyclic nucleosides.