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

Jibin Zheng; Hongyu Chen; Jintao Shang; Lvfeng Zhang; Youling Liang; Dongsheng Chang; You Yang

doi:10.1002/cjoc.202400866

Chinese Journal of Chemistry ›› 2025, Vol. 43 ›› Issue (2) : 169 -174. DOI: 10.1002/cjoc.202400866

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

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Abstract

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 Ph ₃PO-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.

Keywords

Carbohydrates / Protecting groups / Glycosylation / Glycolipids / Glycosides / Photocatalysis / Gold catalysis / Synthetic methods

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Jibin Zheng, Hongyu Chen, Jintao Shang, Lvfeng Zhang, Youling Liang, Dongsheng Chang, You Yang. Photolabile ortho-Nitro-Benzyl Carbonate as a Permanent Hydroxyl Protecting Group for the Synthesis of Digalactosyl Diacylglycerol. Chinese Journal of Chemistry, 2025, 43(2): 169-174 DOI:10.1002/cjoc.202400866