Photolabile ortho-Nitro-Benzyl Carbonate as a Permanent Hydroxyl Protecting Group for the Synthesis of Digalactosyl Diacylglycerol
Jibin Zheng
Shanghai Frontiers Science Center of Optogenetic Techniques for Cell Metabolism, Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai, 200237 China
Search for more papers by this authorHongyu Chen
Shanghai Frontiers Science Center of Optogenetic Techniques for Cell Metabolism, Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai, 200237 China
Search for more papers by this authorJintao Shang
Shanghai Frontiers Science Center of Optogenetic Techniques for Cell Metabolism, Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai, 200237 China
Search for more papers by this authorLvfeng Zhang
Shanghai Frontiers Science Center of Optogenetic Techniques for Cell Metabolism, Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai, 200237 China
Search for more papers by this authorYouling Liang
Shanghai Frontiers Science Center of Optogenetic Techniques for Cell Metabolism, Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai, 200237 China
Search for more papers by this authorDongsheng Chang
Shanghai Frontiers Science Center of Optogenetic Techniques for Cell Metabolism, Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai, 200237 China
Search for more papers by this authorCorresponding Author
You Yang
Shanghai Frontiers Science Center of Optogenetic Techniques for Cell Metabolism, Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai, 200237 China
Engineering Research Center of Pharmaceutical Process Chemistry, Ministry of Education, East China University of Science and Technology, 130 Meilong Road, Shanghai, 200237 China
E-mail: [email protected]Search for more papers by this authorJibin Zheng
Shanghai Frontiers Science Center of Optogenetic Techniques for Cell Metabolism, Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai, 200237 China
Search for more papers by this authorHongyu Chen
Shanghai Frontiers Science Center of Optogenetic Techniques for Cell Metabolism, Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai, 200237 China
Search for more papers by this authorJintao Shang
Shanghai Frontiers Science Center of Optogenetic Techniques for Cell Metabolism, Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai, 200237 China
Search for more papers by this authorLvfeng Zhang
Shanghai Frontiers Science Center of Optogenetic Techniques for Cell Metabolism, Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai, 200237 China
Search for more papers by this authorYouling Liang
Shanghai Frontiers Science Center of Optogenetic Techniques for Cell Metabolism, Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai, 200237 China
Search for more papers by this authorDongsheng Chang
Shanghai Frontiers Science Center of Optogenetic Techniques for Cell Metabolism, Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai, 200237 China
Search for more papers by this authorCorresponding Author
You Yang
Shanghai Frontiers Science Center of Optogenetic Techniques for Cell Metabolism, Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai, 200237 China
Engineering Research Center of Pharmaceutical Process Chemistry, Ministry of Education, East China University of Science and Technology, 130 Meilong Road, Shanghai, 200237 China
E-mail: [email protected]Search for more papers by this authorComprehensive Summary
Traditional protecting groups are often removed under harsh conditions with potentially hazardous reagents, thereby impeding the convenient synthesis of oligosaccharides and glycosides. Herein, we present to utilize the photolabile ortho-nitro-benzyl carbonate (oNBC) as a permanent hydroxyl protecting group for stereocontrolled synthesis of glycosides. The Ph3PO-modulated glycosylation with strongly disarmed per-O-oNBC-protected glycosyl ynenoates preferred to afford glycosides with excellent α-selectivities via the β-phosphonium transition state. Based on the oNBC-mediated galactosylation, synthesis of the glycolipid digalactosyl diacylglycerol (DGDG) containing six double bonds and two esters was achieved in a straightforward manner.
Supporting Information
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