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Synthesis 2024; 56(07): 1157-1166
DOI: 10.1055/s-0042-1751505
paper
Emerging Trends in Glycoscience

Diastereoselective Synthesis of Carbohydrate Conjugates: Pyrano[3,2-c]quinolones

Sumit Kumar
a   Bioorganic Laboratory, Department of Chemistry, University of Delhi, Delhi-110 007, India
,
Aditi Arora
a   Bioorganic Laboratory, Department of Chemistry, University of Delhi, Delhi-110 007, India
,
Sandeep Kumar 
a   Bioorganic Laboratory, Department of Chemistry, University of Delhi, Delhi-110 007, India
b   Department of Chemistry, Ramjas College, University of Delhi, Delhi-110 007, India
,
Priti Kumari
a   Bioorganic Laboratory, Department of Chemistry, University of Delhi, Delhi-110 007, India
,
Sunil K. Singh
c   Department of Chemistry, Kirori Mal College, University of Delhi, Delhi-110 007, India
,
Brajendra K. Singh∗
a   Bioorganic Laboratory, Department of Chemistry, University of Delhi, Delhi-110 007, India
› Author AffiliationsWe are grateful for the financial support provided to advance research and development by the Institute of Eminence at the University of Delhi. Sumit Kumar [File No. 09/045(1798)/2020-EMR-I] and Aditi Arora [File No. 09/0045(11270)/2021-EMR-I] thank the Council of Scientific and Industrial Research, New Delhi, for the award of Senior Research Fellowship (SRF) and Junior Research Fellowship (JRF), respectively.
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We dedicate this article to the fond memory of Late Prof. Ashok K. Prasad.

Abstract

A facile and efficient protocol for the diastereoselective synthesis of pyrano[3,2-c]quinolone carbohydrate derivatives from Perlin aldehydes and 4-hydroxyquinolones has been developed using a one-pot condensation at room temperature. In this investigation, glucose and galactose were employed as inexpensive starting materials to synthesize two sets of pyrano[3,2-c]quinolone-based carbohydrate conjugates. A total of sixteen novel compounds were successfully synthesized using this methodology in good to excellent yields. The reaction exhibited remarkable diastereoselectivity, resulting in a single diastereomeric product with a diastereomeric excess (dr) 97:3 for glucose, while a diastereomeric mixture with a diastereomeric excess (dr) 67:33 was obtained for galactose. The structural characterization of all sixteen compounds was carried out using various analytical techniques, including IR, 1H NMR, 13C NMR, 1H-1H COSY, 1H-13C HETCOR experiments, 2D NOESY NMR, and HRMS data. Additionally, the scalability of the protocol was successfully demonstrated by synthesizing one of the compounds on a gram scale, highlighting its potential for large-scale production.

Key words

diastereoselective synthesis - quinolone - Perlin aldehyde - l-proline - pyranoquinolone - organocatalyst

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0042-1751505.
  • Supporting Information


Publication History

Received: 31 July 2023

Accepted after revision: 07 September 2023

Article published online:
17 October 2023

© 2023. Thieme. All rights reserved

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  • References

  • 1 Uppal J, Mir PA, Chawla A, Kumar N, Kaur G, Bedi PM. S, Bhandari DD. J. Heterocycl. Chem. 2023; 60: 369
    Crossref
  • 2 Magedov IV, Manpadi M, Ogasawara MA, Dhawan AS, Rogelj S, Van slambrouck S, Steelant WF. A, Exdokimov NM, Uglinskii PY, Elias EM, Knee EJ, Tongwa P, Antipin MY, Kornienko A. J. Med. Chem. 2008; 51: 2561
    CrossrefPubMed
  • 3 Elshaier YA, Aly AA, El-Aziz MA, Fathy HM, Brown AB, Ramadan M. Mol. Diversity 2022; 26: 2341
    CrossrefPubMed
  • 4 Ito C, Itoigawa M, Furukawa A, Hirano T, Murata T, Kaneda N, Hisada Y, Okuda K, Furukawa H. J. Nat. Prod. 2004; 67: 1800
    CrossrefPubMed
  • 5 Cantrell CL, Schrader KK, Mamonov LK, Sitpaeva GT, Kustova TS, Dunbar C, Wedge DE. J. Agric. Food Chem. 2005; 53: 7741
    CrossrefPubMed
  • 6 Michael JP. Nat. Prod. Rep. 2008; 25: 166
    CrossrefPubMed
  • 7 Kamperdick C, Van N NH, Sung TV, Adam G. Phytochemistry 1999; 50: 177
    Crossref
  • 8 Chen IS, Wu SJ, Tsai IL, Wu TS, Pezzuto JM, Lu MC, Chai H, Suh N, Teng CM. J. Nat. Prod. 1994; 57: 1206
    CrossrefPubMed
  • 9 Kamikawa T, Hanaoka Y, Fujie S, Saito K, Yamagiwa Y, Fukuhara K, Kubo I. Bioorg. Med. Chem. 1996; 4: 1317
    CrossrefPubMed
  • 10 Butenschön I, Möller K, Hänsel W. J. Med. Chem. 2001; 44: 1249
    CrossrefPubMed
  • 11 Jung EJ, Park BH, Lee YR. Green Chem. 2010; 12: 2003
    Crossref
  • 12 Mulwad VV, Suryanarayan V. Indian J. Heterocycl. Chem. 1996; 5: 281
  • 13 Cipolla L, Ferla BL, Airoldi C, Zona C, Orsato A, Shaikh N, Russo L, Nicotra F. Future Med. Chem. 2010; 2: 587
    CrossrefPubMed
  • 14 Helenius A, Aebi M. Science 2001; 291: 2364
    CrossrefPubMed
  • 15 Henin Y, Gouyette C, Schwartz O, Debouzy JC, Neumann JM, Huynh-Dinh T. J. Med. Chem. 1991; 34: 1830
    CrossrefPubMed
  • 16 Pohl J, Bertram B, Hilgard P, Nowrousian MR, Stüben J, Wiessler B. Cancer Chemother. Pharmacol. 1995; 35: 364
    CrossrefPubMed
  • 17 Tiwari VK, Mishra RC, Sharma A, Tripathi RP. Mini Rev. Med. Chem. 2012; 12: 1497
    CrossrefPubMed
  • 18 Kumar S, Arora A, Kumar R, Senapati NN, Singh BK. Carbohydr. Res. 2023; 530: 108857
    CrossrefPubMed
  • 19 Hollingsworth RI, Wang G. Chem. Rev. 2000; 100: 4267
    CrossrefPubMed
  • 20 Ramesh NG, Balasubramanian KK. Eur. J. Org. Chem. 2003; 4477
    Crossref
  • 21 Arora A, Kumar S, Khatri V, Prasad AK, Chhatwal RJ, Kumar S. Synthesis 2023; in press; DOI: 10.1055/a-2066-1659.
    Article in Thieme Connect
  • 22 Kumar S, Maity J, Kumar B, Kumar S, Prasad AK. Beilstein J. Org. Chem. 2022; 18: 95
    CrossrefPubMed
  • 23 Kumar S, Kumar S, Maity J, Kumar B, Mehta SB, Prasad AK. New J. Chem. 2021; 45: 16635
    Crossref
  • 24 Matta A, Sharma AK, Tomar S, Cao P, Kumar S, Balwani S, Ghosh B, Prasad AK, Van der Eycken EV, DePass AL, Wengel J, Parmar VS, Len C, Singh BK. New J. Chem. 2020; 44: 13716
    Crossref
  • 25 Reddy L, Raghava V, Kumar V, Sagar R, Shaw AK. Chem. Rev. 2013; 113: 3605
    CrossrefPubMed
  • 26 Gonzalez F, Lesage S, Perlin AS. Carbohydr. Res. 1975; 42: 267
    Crossref
  • 27 McLaughlin MJ, Hsung RP. J. Org. Chem. 2001; 66: 1049
    CrossrefPubMed
  • 28 De Groot A, Jansen BJ. M. Tetrahedron Lett. 1975; 16: 3407
    Crossref
  • 29 Coleman MA, Burchill L, Sumby CJ, George JH. Org. Lett. 2019; 21: 8776
    CrossrefPubMed
  • 30 Lee YR, Kim DH, Shim J.-J, Kim SK, Park JH, Cha JS, Lee CS. Bull. Korean Chem. Soc. 2002; 23: 998
    Crossref
  • 31 Lee YR, Kweon HI, Koh WS, Min KR, Kim Y, Lee SH. Synthesis 2001; 1851
    Article in Thieme Connect
  • 32 Shen HC, Wang J, Cole KP, McLaughlin MJ, Morgan CD, Douglas CP, Hsung RP, Coverdale HA, Gerasyuto AI, Hahn JM, Liu J, Sklenicka HM, Wei LL, Zehnder LR, Zificsak CA. J. Org. Chem. 2003; 68: 1729
    CrossrefPubMed
  • 33 Thorat BR, Mali SN, Wavhal SS, Bhagat DS, Borade RM, Chapolikar A, Gandhi A, Shinde P. Comb. Chem. High Throughput Screening 2023; 26: 1108
    CrossrefPubMed
  • 34 Mukhopadhyay C, Tapaswi PK, Butcher RJ. Tetrahedron Lett. 2010; 51: 1797
    Crossref
  • 35 List B, Castello C. Synlett 2001; 1687
    Article in Thieme Connect
  • 36 Hua DH, Chen Y, Sin H.-S, Maroto MJ, Robinson PD, Newell SW, Perchellet EM, Ladesich JB, Freeman JA, Perchellet J.-P, Chiang PK. J. Org. Chem. 1997; 62: 6888
    Crossref
  • 37 Nicholas SD, Smith F. Nature 1948; 161: 349
    CrossrefPubMed
  • 38 Bay S, Huteau V, Zarantonelli M.-L, Pires R, Ughetto-Monfrin J, Taha M.-K, England P, Lafaye P. J. Med. Chem. 2004; 47: 3916
    CrossrefPubMed
  • 39 Zhao J, Wei S, Ma X, Shao H. Green Chem. 2009; 11: 1124
    Crossref
  • 40 Arya K, Agarwal M. Bioorg. Med. Chem. Lett. 2007; 17: 86
    CrossrefPubMed
  • 41 Park SJ, Lee JC, Lee KI. Bull. Korean Chem. Soc. 2007; 28: 1203
    Crossref
  • 42 Buckle DR, Cantello BC. C, Smith H, Spicer BA. J. Med. Chem. 1975; 18: 726
    CrossrefPubMed
  • 43 Kumari P, Narayana C, Dubey S, Gupta A, Sagar R. Org. Biomol. Chem. 2018; 16: 2049
    CrossrefPubMed
  • 44 Hunsen M, Long DA, D’Ardenne CR, Smith AL. Carbohydr. Res. 2005; 340: 2670
    CrossrefPubMed
  • 45 Kabalka GW, Ju Y, Wu Z. J. Org. Chem. 2003; 68: 7915
    CrossrefPubMed
  • 46 Mahato SK, Vinayagam J, Dey S, Timiri AK, Chatterjee S, Jaisankar P. Aust. J. Chem. 2012; 66: 241
    Crossref
  • 47 Li X, Xiao T, He G, Zhu S, Zhu D, Shen R. Adv. Synth. Catal. 2021; 364: 622
    Crossref
  • 48 Hsung RP, Shen HC, Douglas CJ, Morgan CD, Degen SJ, Yao LJ. J. Org. Chem. 1999; 64: 690
    CrossrefPubMed