Stereoselective Protection-Free Modification of 3-Keto-saccharides
Nittert Marinus
1
,
Nabil Tahiri
1
,
Margherita Duca
1
,
L M C Marc Mouthaan
1
,
Simona Bianca
1
,
Marco Van Den Noort
2
,
Bert Poolman
2
,
Martin D Witte
1
,
Publication type: Journal Article
Publication date: 2020-07-07
scimago Q1
wos Q1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
PubMed ID:
32635733
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
Unprotected 3-keto-saccharides have become readily accessible via site-selective oxidation, but their protection-free functionalization is relatively unexplored. Here we show that protecting groups are obsolete in a variety of stereoselective modifications of our model substrate methyl α-glucopyranoside. This allows the preparation of rare sugars and the installation of click handles and reactive groups. To showcase the applicability of the methodology, maltoheptaose has been converted into a chemical probe, and the rare sugar evalose has been synthesized.
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Total citations:
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Citations from 2025:
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GOST
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Marinus N. et al. Stereoselective Protection-Free Modification of 3-Keto-saccharides // Organic Letters. 2020. Vol. 22. No. 14. pp. 5622-5626.
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Marinus N., Tahiri N., Duca M., Mouthaan L. M. C. M., Bianca S., Van Den Noort M., Poolman B., Witte M. D., Minnaard A. J. Stereoselective Protection-Free Modification of 3-Keto-saccharides // Organic Letters. 2020. Vol. 22. No. 14. pp. 5622-5626.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1021/acs.orglett.0c01986
UR - https://doi.org/10.1021/acs.orglett.0c01986
TI - Stereoselective Protection-Free Modification of 3-Keto-saccharides
T2 - Organic Letters
AU - Marinus, Nittert
AU - Tahiri, Nabil
AU - Duca, Margherita
AU - Mouthaan, L M C Marc
AU - Bianca, Simona
AU - Van Den Noort, Marco
AU - Poolman, Bert
AU - Witte, Martin D
AU - Minnaard, Adriaan J.
PY - 2020
DA - 2020/07/07
PB - American Chemical Society (ACS)
SP - 5622-5626
IS - 14
VL - 22
PMID - 32635733
SN - 1523-7060
SN - 1523-7052
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2020_Marinus,
author = {Nittert Marinus and Nabil Tahiri and Margherita Duca and L M C Marc Mouthaan and Simona Bianca and Marco Van Den Noort and Bert Poolman and Martin D Witte and Adriaan J. Minnaard},
title = {Stereoselective Protection-Free Modification of 3-Keto-saccharides},
journal = {Organic Letters},
year = {2020},
volume = {22},
publisher = {American Chemical Society (ACS)},
month = {jul},
url = {https://doi.org/10.1021/acs.orglett.0c01986},
number = {14},
pages = {5622--5626},
doi = {10.1021/acs.orglett.0c01986}
}
Cite this
MLA
Copy
Marinus, Nittert, et al. “Stereoselective Protection-Free Modification of 3-Keto-saccharides.” Organic Letters, vol. 22, no. 14, Jul. 2020, pp. 5622-5626. https://doi.org/10.1021/acs.orglett.0c01986.