Ring opening of cyclopropylmethylidene with trimethylaluminum: Synthesis of 1-cyclopropylethyl ether as an acid labile protecting group for hydroxyl Protection and carbohydrate synthesis

IF 1.2 4区化学 Q4 BIOCHEMISTRY & MOLECULAR BIOLOGY

Journal of Carbohydrate Chemistry Pub Date : 2025-03-24 DOI:10.1080/07328303.2025.2471354

Madhav Poudel , Zainab Bustani , Xiaohua Li , Jianglong Zhu

引用次数: 0

Abstract

The 4,6-O-cyclopropylmethylidene (CPMD) moiety of a methyl α-glucoside derivative can be regioselectively opened by trimethylaluminum to afford a corresponding 1-cyclopropylethyl (CPE) ether at C4 and a free alcohol at C6. This 1-CPE ether was found to be an acid-labile hydroxyl protecting group and can be readily cleaved using 10% trifluoracetic acid in dichloromethane at room temperature. The utilization of 1-CPE ether as a hydroxyl protecting group has been demonstrated in the efficient synthesis of a trisaccharide.

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来源期刊

Journal of Carbohydrate Chemistry 化学-生化与分子生物学

CiteScore

2.10

自引率

0.00%

发文量

审稿时长

1 months

期刊介绍： The Journal of Carbohydrate Chemistry serves as an international forum for research advances involving the chemistry and biology of carbohydrates. The following aspects are considered to fall within the scope of this journal: -novel synthetic methods involving carbohydrates, oligosaccharides, and glycoconjugates- the use of chemical methods to address aspects of glycobiology- spectroscopic and crystallographic structure studies of carbohydrates- computational and molecular modeling studies- physicochemical studies involving carbohydrates and the chemistry and biochemistry of carbohydrate polymers.