Photolabile ortho‐Nitro‐Benzyl Carbonate as a Permanent Hydroxyl Protecting Group for the Synthesis of Digalactosyl Diacylglycerol

Comprehensive 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 perma...

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Bibliographic Details
Published in:Chinese journal of chemistry 2024-10, Vol.43 (2), p.169-174
Main Authors: Zheng, Jibin, Chen, Hongyu, Shang, Jintao, Zhang, Lvfeng, Liang, Youling, Chang, Dongsheng, Yang, You
Format: Article
Language:English
Subjects:
Carbohydrates
Diglycerides
Esters
Glycolipids
Glycosides
Glycosylation
Gold catalysis
Oligosaccharides
Photocatalysis
Protecting groups
Reagents
Synthesis
Synthetic methods
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Summary:Comprehensive 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. The photolabile ortho‐nitro‐benzyl carbonate (oNBC) was utilized as a permanent hydroxyl protecting group for effective synthesis of digalactosyl diacylglycerol (DGDG) containing six double bonds and two esters.
ISSN:1001-604X
1614-7065
DOI:10.1002/cjoc.202400866