Synthetic strategy for polyhydroxylated indolizidine iminosugar from sugar-derived HWE precursor

IF 2.4 3区化学 Q3 BIOCHEMISTRY & MOLECULAR BIOLOGY

Carbohydrate Research Pub Date : 2024-11-01 DOI:10.1016/j.carres.2024.109302

Nagaraja Ingaladal , Ravi S. Lankalapalli

引用次数: 0

Abstract

The diversity of polyhydroxylated indolizidine (PI) iminosugars is ever-expanding due to the wide range of methods developed and substrate choice during synthesis. This study used an HWE precursor derived from d-glucose to extend the chain length at the C1 position. A double reductive amination and dihydroxylation of the resulting olefin, followed by intramolecular cyclization, enabled the successful synthesis of a new PI. In addition, the precursor intermediate for Mitsunobu reaction was utilized in synthesis of a new iminononulol.

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从糖源 HWE 前体合成多羟基吲嗪亚氨基糖的策略

由于合成方法和底物选择的广泛性，多羟基吲哚嗪（PI）亚氨基糖的多样性不断扩大。本研究使用一种源自 d-葡萄糖的 HWE 前体来延长 C1 位置的链长。对得到的烯烃进行双还原胺化和二羟基化，然后进行分子内环化，成功合成了一种新的 PI。此外，还利用 Mitsunobu 反应的前体中间体合成了一种新的亚氨基壬基酚。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Carbohydrate Research 化学-生化与分子生物学

CiteScore

5.00

自引率

3.20%

发文量

183

审稿时长

3.6 weeks

期刊介绍： Carbohydrate Research publishes reports of original research in the following areas of carbohydrate science: action of enzymes, analytical chemistry, biochemistry (biosynthesis, degradation, structural and functional biochemistry, conformation, molecular recognition, enzyme mechanisms, carbohydrate-processing enzymes, including glycosidases and glycosyltransferases), chemical synthesis, isolation of natural products, physicochemical studies, reactions and their mechanisms, the study of structures and stereochemistry, and technological aspects. Papers on polysaccharides should have a "molecular" component; that is a paper on new or modified polysaccharides should include structural information and characterization in addition to the usual studies of rheological properties and the like. A paper on a new, naturally occurring polysaccharide should include structural information, defining monosaccharide components and linkage sequence. Papers devoted wholly or partly to X-ray crystallographic studies, or to computational aspects (molecular mechanics or molecular orbital calculations, simulations via molecular dynamics), will be considered if they meet certain criteria. For computational papers the requirements are that the methods used be specified in sufficient detail to permit replication of the results, and that the conclusions be shown to have relevance to experimental observations - the authors'' own data or data from the literature. Specific directions for the presentation of X-ray data are given below under Results and "discussion".