Stereoselective Phenylselenoglycosylation of Glycals Bearing a Fused Carbonate Moiety toward the Synthesis of 2-Deoxy-β-galactosides and β-Mannosides
Publication type: Journal Article
Publication date: 2020-03-27
scimago Q1
wos Q1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
PubMed ID:
32216320
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
A phenylselenoglycosylation reaction of glycal derivatives mediated by diphenyl diselenide and phenyliodine(III) bis(trifluoroacetate) under mild conditions is described. Stereoselective glycosylation has been achieved by installing fused carbonate on those glycals. 3,4-O-Carbonate galactals and 2,3-O-carbonate 2-hydroxyglucals are converted into corresponding glycosides in good yields with excellent β-selectivity, resulting in 2-phenylseleno-2-deoxy-β-galactosides and 2-phenylseleno-β-mannosides which are good precursors of 2-deoxy-β-galactosides and β-mannosides, respectively.
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23
Total citations:
23
Citations from 2025:
8
(34.78%)
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GOST
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Meng S. et al. Stereoselective Phenylselenoglycosylation of Glycals Bearing a Fused Carbonate Moiety toward the Synthesis of 2-Deoxy-β-galactosides and β-Mannosides // Organic Letters. 2020. Vol. 22. No. 8. pp. 2981-2986.
GOST all authors (up to 50)
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Meng S., Zhong W., Yao W., Li Z. J. Stereoselective Phenylselenoglycosylation of Glycals Bearing a Fused Carbonate Moiety toward the Synthesis of 2-Deoxy-β-galactosides and β-Mannosides // Organic Letters. 2020. Vol. 22. No. 8. pp. 2981-2986.
Cite this
RIS
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TY - JOUR
DO - 10.1021/acs.orglett.0c00732
UR - https://doi.org/10.1021/acs.orglett.0c00732
TI - Stereoselective Phenylselenoglycosylation of Glycals Bearing a Fused Carbonate Moiety toward the Synthesis of 2-Deoxy-β-galactosides and β-Mannosides
T2 - Organic Letters
AU - Meng, Shuai
AU - Zhong, Wenhe
AU - Yao, Wang
AU - Li, Zhong Jun
PY - 2020
DA - 2020/03/27
PB - American Chemical Society (ACS)
SP - 2981-2986
IS - 8
VL - 22
PMID - 32216320
SN - 1523-7060
SN - 1523-7052
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2020_Meng,
author = {Shuai Meng and Wenhe Zhong and Wang Yao and Zhong Jun Li},
title = {Stereoselective Phenylselenoglycosylation of Glycals Bearing a Fused Carbonate Moiety toward the Synthesis of 2-Deoxy-β-galactosides and β-Mannosides},
journal = {Organic Letters},
year = {2020},
volume = {22},
publisher = {American Chemical Society (ACS)},
month = {mar},
url = {https://doi.org/10.1021/acs.orglett.0c00732},
number = {8},
pages = {2981--2986},
doi = {10.1021/acs.orglett.0c00732}
}
Cite this
MLA
Copy
Meng, Shuai, et al. “Stereoselective Phenylselenoglycosylation of Glycals Bearing a Fused Carbonate Moiety toward the Synthesis of 2-Deoxy-β-galactosides and β-Mannosides.” Organic Letters, vol. 22, no. 8, Mar. 2020, pp. 2981-2986. https://doi.org/10.1021/acs.orglett.0c00732.