Synonyms:DL-Mannose,6-deoxy-;Rhamnose (8CI);6-Deoxy-DL-mannose;6-Deoxymannose;DL-Rhamnose;
99% *data from raw suppliers
There total 86 articles about Rhamnose which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:
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(2S,3S,4S,5S,6R)-2-methoxy-6-methyltetrahydro-2H-pyran-3,4,5-triol
The study investigates the application of the [p-(trimethylsilyl)ethoxy]methyl (SEM) acetal as a protecting group in carbohydrate chemistry, specifically in the synthesis of oligosaccharides. The researchers used allyl 2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside as a starting monosaccharide and protected its remaining 3-OH group with SEM acetal. They demonstrated the SEM group's compatibility with various protection/deprotection conditions, such as acid catalysis for removal and stability under glycosylation conditions. The study also involved converting the protected monosaccharide into glycosyl donors and acceptors through a series of reactions, including isomerization, hydrolysis, and treatment with Vilsmeier-Haack reagents. These fully functionalized rhamnose acceptors and donors were then used in glycosylation reactions to produce disaccharides, which can serve as synthons for higher order oligosaccharides. The SEM protecting group was found to be advantageous due to its mild removal conditions and stability under different reaction conditions, making it a valuable tool for oligosaccharide synthesis.
The research focuses on the synthesis of muscarine analogues, specifically the epimeric 3-hydroxymuscarines (5 and 9), from L-rhamnose. The purpose of this study is to explore the potential of these analogues in providing insights into selective interactions with muscarinic receptors, which could lead to the development of chemotherapeutically useful compounds as specific muscarinic agonists or antagonists. The key chemicals involved include L-rhamnose as the starting material, various reagents such as triflic anhydride, lithium aluminum hydride, and tosyl chloride, and protecting groups like tert-butyldiphenylsilyl chloride. The synthesis involves multiple steps, including oxidation, esterification, reduction, and selective protection and deprotection of hydroxyl groups. The study concludes that L-rhamnose is a valuable precursor for the synthesis of muscarine and its analogues, and the tetrahydrofuran intermediate (7) is highly divergent for the synthesis of muscarine derivatives with functional groups at the C-3 position. The biological properties of these hydroxymuscarines and other analogues will be reported elsewhere.
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