Regioselective One-Pot Benzoylation of Triol and Tetraol Arrays in Carbohydrates
| Type of Publication: | Journal article |
| Publication status: | Published |
| Author: | Li, Tong; Li, Tianlu; Cui, Tongxiao; Sun, Yajing; Wang, Fengshan; Cao, Hongzhi; Schmidt, Richard R.; Peng, Peng |
| Year of publication: | 2018 |
| Published in: | Organic Letters ; 20 (2018), 13. - pp. 3862-3865. - ISSN 1523-7060. - eISSN 1523-7052 |
| Pubmed ID: | 29932662 |
| DOI (citable link): | https://dx.doi.org/10.1021/acs.orglett.8b01446 |
| Summary: |
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.
|
| Subject (DDC): | 540 Chemistry |
| Bibliography of Konstanz: | Yes |
| Refereed: | Yes |
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LI, 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. 20(13), pp. 3862-3865. ISSN 1523-7060. eISSN 1523-7052. Available under: doi: 10.1021/acs.orglett.8b01446
@article{Li2018Regio-43542, title={Regioselective One-Pot Benzoylation of Triol and Tetraol Arrays in Carbohydrates}, year={2018}, doi={10.1021/acs.orglett.8b01446}, 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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