ChemistryOpen | |
Organocatalytic Synthesis of Higher‐Carbon Sugars: Efficient Protocol for the Synthesis of Natural Sedoheptulose and d‐Glycero‐l‐galacto‐oct‐2‐ulose | |
Oskar Popik1  Dr. Monika Pasternak-Suder2  Dr. Sebastian Baś2  | |
[1] Institute of Organic Chemistry, Polish Academy of Sciences, Warsaw, Poland;Faculty of Chemistry, Jagiellonian University, Krakow, Poland | |
关键词: aldol reaction; asymmetric synthesis; carbohydrates; natural products; organocatalysis; | |
DOI : 10.1002/open.201500099 | |
来源: Wiley | |
【 摘 要 】
Herein we report a short and efficient protocol for the synthesis of naturally occurring higher-carbon sugars—sedoheptulose (d-altro-hept-2-ulose) and d-glycero-l-galacto-oct-2-ulose—from readily available sugar aldehydes and dihydroxyacetone (DHA). The key step includes a diastereoselective organocatalytic syn-selective aldol reaction of DHA with d-erythrose and d-xylose, respectively. The methodology presented can be expanded to the synthesis of various higher sugars by means of syn-selective carbon–carbon-bond-forming aldol reactions promoted by primary-based organocatalysts. For example, this methodology provided useful access to d-glycero-d-galacto-oct-2-ulose and 1-deoxy-d-glycero-d-galacto-oct-2-ulose from d-arabinose in high yield (85 and 74 %, respectively) and high stereoselectivity (99:1).Abstract
【 授权许可】
CC BY-NC-ND
© 2015 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.
Creative Commons Attribution-NonCommercial-NoDerivs License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non-commercial and no modifications or adaptations are made.
【 预 览 】
Files | Size | Format | View |
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RO202107150004580ZK.pdf | 428KB | download |