Journal article

Epimerization of C5 of an N-hydroxypyrrolidine in the synthesis of swainsonine related iminosugars

Abstract:: Epimerization of C5 of an N-hydroxypyrrolidine ring by regioselective oxidation to a nitrone followed by diastereoselective reduction provides a newapproachto the synthesis of swainsonine and related compounds. The only protection in the synthesis of the potent mannosidase inhibitor DIM (1, 4-dideoxy-1,4-imino-D-mannitol) was the acetonation of D-mannose.

Publication status:: Published

Peer review status:: Peer reviewed

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APA Style

Qian, B., Kamori, A., Kinami, K., Kato, A., Li, Y., Fleet, G., & Yu, C. (2016). Epimerization of C5 of an N-hydroxypyrrolidine in the synthesis of swainsonine related iminosugars. Organic and Biomolecular Chemistry, 14(19), 4488–4498.

MLA Style

Qian, B, et al. “Epimerization of C5 of an N-Hydroxypyrrolidine in the Synthesis of Swainsonine Related Iminosugars.” Organic and Biomolecular Chemistry, vol. 14, no. 19, 2016, pp. 4488–98.

Chicago Style

Qian, B, A Kamori, K Kinami, et al. 2016. “Epimerization of C5 of an N-Hydroxypyrrolidine in the Synthesis of Swainsonine Related Iminosugars.” Organic and Biomolecular Chemistry 14 (19): 4488–98.
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Files:: Fleet et al, Epimerization of C5 of an N-hydroxypyrrolidine in...

(Preview, Accepted manuscript, pdf, 906.3KB, Terms of use)

Publisher copy:: 10.1039/c6ob00531d

Authors

+ Qian, B More by this author

Role:: Author

+ Kamori, A More by this author

Role:: Author

+ Kinami, K More by this author

Role:: Author

+ Kato, A More by this author

Role:: Author

+ Li, Y More by this author

Role:: Author

More authors...

+ Japanese Society for the Promotion of Science More from this funder

Grant:: 26460143

+ National Science and Technology Major Projects More from this funder

Grant:: 2013ZX09508104

+ National Natural Science Foundation of China More from this funder

Grant:: 21202173

+ Ministry of Science and Technology of P. R. China More from this funder

Grant:: 2012CB822101

+ Leverhulme Trust More from this funder

Funding agency for:: Fleet, G

More funders...

Publisher:: Royal Society of Chemistry
Journal:: Organic and Biomolecular Chemistry More from this journal
Volume:: 14
Issue:: 19
Pages:: 4488-4498
Publication date:: 2016-04-01
Acceptance date:: 2016-04-14
DOI:: 10.1039/c6ob00531d
EISSN:: 1477-0539
ISSN:: 1477-0520

Pubs id:: pubs:626333
UUID:: uuid:08759600-fc77-4503-9308-b5a5c20042e5
Local pid:: pubs:626333
Source identifiers:: 626333
Deposit date:: 2016-07-04
ARK identifier:: ark:/29072/ora_08759600fc7745039308b5a5c20042e5

Terms of use

Copyright holder:: Royal Society of Chemistry
Copyright date:: 2016
Notes:: © Royal Society of Chemistry 2016

Licence:: Terms and Conditions of Use for Oxford University Research Archive

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