环丙基甲基乙烯与三甲基铝开环：1-环丙基乙醚的合成，作为羟基保护和碳水化合物合成的酸不稳定保护基团

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

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引用次数: 0

摘要

甲基α-葡萄糖苷衍生物的4,6- o -环丙基甲基（CPMD）部分可以被三甲基铝选择性地打开，在C4上得到相应的1-环丙基乙基（CPE）醚和在C6上得到游离醇。该1-CPE醚被发现是一种酸不稳定的羟基保护基团，在室温下用10%的三氟乙酸在二氯甲烷中很容易裂解。利用1-CPE醚作为羟基保护基团，有效合成了一种三糖。

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

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.