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

被引：0
作者：
Poudel, Madhav [1 ,2 ]
Bustani, Zainab [3 ]
Li, Xiaohua [3 ]
Zhu, Jianglong [1 ,2 ]
机构：
[1] Univ Toledo, Dept Chem & Biochem, Toledo, OH 43606 USA
[2] Univ Toledo, Sch Green Chem & Engn, Toledo, OH 43606 USA
[3] Univ Michigan Dearborn, Dept Nat Sci, Dearborn, MI 48128 USA
来源：
JOURNAL OF CARBOHYDRATE CHEMISTRY | 2025年 / 44卷 / 1-3期
关键词：
Cyclopropylmethylidene; 1-cyclopropylethyl ether; protecting group; carbohydrate; GLYCOSIDE REACTIVITY;
D O I：
10.1080/07328303.2025.2471354
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
The 4,6-O-cyclopropylmethylidene (CPMD) moiety of a methyl alpha-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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页码：81 / 93
页数：13
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