Asymmetric syntheses of methyl N-Boc-2-deoxy-2-amino-l-erythroside,methyl N-Boc-2-deoxy-2-amino-d-threoside and methyl N-Boc-2,3-dideoxy-3-amino-l-arabinopyranoside |
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| Institution: | 1. Faculty of Chemistry, University of Gdansk, Wita Stwosza 63, 80-308 Gdansk, Poland;2. School of Science and Technology, Nottingham Trent University, Clifton Lane, Nottingham NG11 8NS, United Kingdom;3. Department of Medical Microbiology, Medical University of Gdansk, Do Studzienki 38, 80-227 Gdansk, Poland;1. Henan University of Traditional Chinese Medicine, Zhengzhou 450008, China;2. School of Chemistry and Chemical Engineering, Huazhong University of Science and Technology, Wuhan 430074, China;1. Seed Biology, Department of Crop and Soil Sciences, Cornell University, Ithaca, NY 14853-1901, USA;2. Department of Chemistry and Chemical Biology, Cornell University, Ithaca, NY 14853, USA;3. School of Pharmacy and Queensland Alliance for Agriculture and Food Innovation, University of Queensland, Brisbane, Queensland 4072, Australia;1. Instituto de Química Rosario (CONICET-UNR), Facultad de Ciencias Bioquímicas y Farmacéuticas, Suipacha 531, 2000 Rosario, Argentina;2. Departamento de Química Orgánica-CIHIDECAR, Facultad de Ciencias Exactas y Naturales, UBA, Ciudad Universitaria, Pab. 2, 1428 Buenos Aires, Argentina;1. The State Key Laboratory of Stem Cell and Reproductive Biology, Institute of Zoology, Chinese Academy of Sciences, Beijing 100101, PR China;2. University of Chinese Academy of Sciences, Beijing 100049, PR China |
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| Abstract: | The asymmetric syntheses of methyl N-Boc-2-deoxy-2-amino-l-erythroside and methyl N-Boc-2-deoxy-2-amino-d-threoside have been achieved from sorbic acid, in six and eight steps, and in 35 and 13% overall yield, respectively. Diastereoselective aminohydroxylation of tert-butyl sorbate gives access to two diastereoisomeric α-hydroxy-β-amino-γ,δ-unsaturated esters. Reduction of the ester functionality and ozonolysis of the double bond gives the corresponding aldehyde, which exists exclusively in the ring-closed (furanose) form. An alternative synthesis of methyl N-Boc-2-deoxy-2-amino-l-erythroside was also developed, reliant on aminohydroxylation of an α,β-unsaturated ester bearing an acetal functionality at the γ-position, and this synthesis proceeded in five steps and 54% overall yield from acrolein diethyl acetal. This approach was extended to permit the synthesis of methyl N-Boc-2,3-dideoxy-3-amino-l-arabinopyranoside in six steps and 58% overall yield from ethyl 3,3-diethoxypropanote. |
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| Keywords: | Amino sugar Asymmetric synthesis Conjugate addition Lithium amide |
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