Efficient Synthesis of N-Benzyloxycarbonyl-2-aminoalkanesulfonyl Chlorides with Functionalized Side Chains
Publication type: Journal Article
Publication date: 2017-02-07
scimago Q2
wos Q2
SJR: 0.559
CiteScore: 4.6
Impact factor: 2.3
ISSN: 00397881, 1437210X
Catalysis
Organic Chemistry
Abstract
N-Benzyloxycarbonyl (Cbz)-protected 2-aminoalkanesulfonyl chlorides are useful building blocks for the synthesis of sulfonopeptides, which are receptor ligands and enzyme inhibitors, and are prepared by the coupling reaction of N-protected aminoalkanesulfonyl chlorides with amino acid or peptide esters. Various N-Cbz-protected 2-aminoalkanesulfonyl chlorides with functionalized side chains were synthesized through the radical addition of different xanthates to benzyl N-allylcarbamate and subsequent oxidative chlorination with tert-butyl hypochlorite under neutral conditions. A mechanism for the oxidative chlorination is proposed. This is a useful and convenient strategy for the synthesis of N-Cbz-protected 2-aminoalkanesulfonyl chlorides with diverse functionalized side-chains.
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Total citations:
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Citations from 2024:
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GOST
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Xu J., Abdellaoui H., Xu J. Efficient Synthesis of N-Benzyloxycarbonyl-2-aminoalkanesulfonyl Chlorides with Functionalized Side Chains // Synthesis. 2017. Vol. 49. No. 10. pp. 2250-2256.
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Xu J., Abdellaoui H., Xu J. Efficient Synthesis of N-Benzyloxycarbonyl-2-aminoalkanesulfonyl Chlorides with Functionalized Side Chains // Synthesis. 2017. Vol. 49. No. 10. pp. 2250-2256.
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TY - JOUR
DO - 10.1055/s-0036-1588706
UR - https://doi.org/10.1055/s-0036-1588706
TI - Efficient Synthesis of N-Benzyloxycarbonyl-2-aminoalkanesulfonyl Chlorides with Functionalized Side Chains
T2 - Synthesis
AU - Xu, Jiaxi
AU - Abdellaoui, Hassane
AU - Xu, Jiaxi
PY - 2017
DA - 2017/02/07
PB - Georg Thieme Verlag KG
SP - 2250-2256
IS - 10
VL - 49
SN - 0039-7881
SN - 1437-210X
ER -
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BibTex (up to 50 authors)
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@article{2017_Xu,
author = {Jiaxi Xu and Hassane Abdellaoui and Jiaxi Xu},
title = {Efficient Synthesis of N-Benzyloxycarbonyl-2-aminoalkanesulfonyl Chlorides with Functionalized Side Chains},
journal = {Synthesis},
year = {2017},
volume = {49},
publisher = {Georg Thieme Verlag KG},
month = {feb},
url = {https://doi.org/10.1055/s-0036-1588706},
number = {10},
pages = {2250--2256},
doi = {10.1055/s-0036-1588706}
}
Cite this
MLA
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Xu, Jiaxi, et al. “Efficient Synthesis of N-Benzyloxycarbonyl-2-aminoalkanesulfonyl Chlorides with Functionalized Side Chains.” Synthesis, vol. 49, no. 10, Feb. 2017, pp. 2250-2256. https://doi.org/10.1055/s-0036-1588706.