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Regioselective One-Pot Benzoylation of Triol and Tetraol Arrays in Carbohydrates

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2018

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Li, Tong
Li, Tianlu
Cui, Tongxiao
Sun, Yajing
Wang, Fengshan
Cao, Hongzhi

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https://doi.org/10.1021/acs.orglett.8b01446
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Organic Letters. 2018, 20(13), pp. 3862-3865. ISSN 1523-7060. eISSN 1523-7052. Available under: doi: 10.1021/acs.orglett.8b01446

Zusammenfassung

Protection of 2,3,4-O-unprotected α-galacto- and α-fucopyranosides with BzCN and DMAP/DIPEA as the base afforded directly and regioselectively the 3-O-unprotected derivatives. The rationale for these studies was to take advantage of the eventual cooperativity of the “cyanide effect” and “the alkoxy group mediated diol effect”. This way, even the totally unprotected α-galactopyranosides could be regioselectively transformed into the corresponding 2,4,6-O-protected derivatives. The great utility of these building blocks was demonstrated in efficient trisaccharide syntheses.

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ISO 690LI, Tong, Tianlu LI, Tongxiao CUI, Yajing SUN, Fengshan WANG, Hongzhi CAO, Richard R. SCHMIDT, Peng PENG, 2018. Regioselective One-Pot Benzoylation of Triol and Tetraol Arrays in Carbohydrates. In: Organic Letters. 2018, 20(13), pp. 3862-3865. ISSN 1523-7060. eISSN 1523-7052. Available under: doi: 10.1021/acs.orglett.8b01446
BibTex
@article{Li2018Regio-43542,
  year={2018},
  doi={10.1021/acs.orglett.8b01446},
  title={Regioselective One-Pot Benzoylation of Triol and Tetraol Arrays in Carbohydrates},
  number={13},
  volume={20},
  issn={1523-7060},
  journal={Organic Letters},
  pages={3862--3865},
  author={Li, Tong and Li, Tianlu and Cui, Tongxiao and Sun, Yajing and Wang, Fengshan and Cao, Hongzhi and Schmidt, Richard R. and Peng, Peng}
}
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