PROPANOL-1

Base Information

• Chemical Name: PROPANOL-1
• CAS No.: 21-23-8
• Mol file: 21-23-8.mol

Synonyms:

Chemical Property of PROPANOL-1

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

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Refernces

Stereoelectronic effects determine oxacarbenium vs β-sulfonium ion mediated glycosylations

10.1021/ol1027267

The study focuses on the stereoelectronic effects that determine whether glycosylations proceed through oxacarbenium or α-sulfonium ion intermediates. The researchers investigated the influence of protecting groups and the constitution of the C-2 chiral auxiliary on the glycosylation pathway and the resulting anomeric outcome. They found that electron-withdrawing protecting groups, such as acetyl esters, favor the formation of α-sulfonium ions, leading to R-glycosides through an SN2-like displacement. In contrast, electron-donating protecting groups, like benzyl ethers, result in a mixture of anomers due to an equilibrium between sulfonium and oxacarbenium ions. The study also highlighted the importance of the chiral auxiliary's constitution, showing that certain substituents can enhance the stability of the sulfonium ion and promote selective glycosylation. These findings provide guidance for selecting glycosyl donors that can achieve exclusive 1,2-cis stereoselectivity in the synthesis of complex oligosaccharides.

Facile synthesis of 1,3,7-trihydroxyxanthone and its regioselective coupling reactions with prenal: Simple and efficient access to osajaxanthone and nigrolineaxanthone F

10.1021/jo0606655

The research aims to develop a simple and efficient method for synthesizing 1,3,7-trihydroxyxanthone and its subsequent regioselective coupling reactions with prenal to exclusively produce the natural products osajaxanthone and nigrolineaxanthone F. The study describes a five-step synthesis of 1,3,7-trihydroxyxanthone starting from 1,3,5-trimethoxybenzene, involving NBS-induced bromination, lithiation, benzoylation, selective deprotection, intramolecular cyclization, and demethylation, achieving an overall yield of 62%. The regioselective coupling reactions with prenal were conducted under different conditions: at room temperature with calcium hydroxide yielding osajaxanthone (75% yield) and under thermal conditions at 140-150 °C yielding nigrolineaxanthone F (98% yield). The study concludes that this approach offers a straightforward and efficient route to these xanthones, with high yields and selectivity, providing a significant improvement over previous methods. The structures of the compounds were confirmed using analytical and spectral data, including X-ray crystallography.