185549-85-3Relevant articles and documents
Synthetic method of rhodiola rosea active ingredient rosavin or rosarin
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Paragraph 0041-0044, (2020/01/03)
The present invention provides a synthetic method of rhodiola rosea active ingredient rosavin or rosarin. A convergent synthetic strategy is adopted, rosin is used as a starting material and modifiedinto sugar acceptors through protection and deprotection strategies, then sugar acceptors and sugar donors formed by arabinopyranose and arabinyl furanose in presence of an accelerator quickly and efficiently conduct synthesis of rosavin and rosarin. The related synthetic method is cheap and easy-to-obtain in raw materials and mild in reaction conditions, the obtained product is high in purity, and compared with currently reported linear synthesis strategy, the method has very good industrialization prospects.
Streamlined synthesis of per-O-acetylated sugars, glycosyl iodides, or thioglycosides from unprotected reducing sugars
Mukhopadhyay, Balaram,Kartha, K.P. Ravindranathan,Russell, David A.,Field, Robert A.
, p. 7758 - 7760 (2007/10/03)
Solvent-free per-O-acetylation of sugars with stoichiometric acetic anhydride and catalytic iodine proceeds in high yield (90-99%) to give exclusively pyranose products as anomeric mixtures. Without workup, subsequent anomeric substitution employing iodine in the presence of hexamethyldisilane (i.e., TMS-I generated in situ) gives the corresponding glycosyl iodides in 75-95% isolated yield. Alternatively, and without workup, further treatment with dimethyl disulfide or thiol (ethanethiol or thiocresol) gives anomerically pure thioglycosides in more than 75% overall yield.
Reaction of sugar thiocyanates with Grignard reagents. New synthesis of thioglycosides
Pakulski, Zbigniew,Pierozynski, Donat,Zamojski, Aleksander
, p. 2975 - 2992 (2007/10/02)
Glycosyl thiocyanates having hydroxyl groups protected with acetyl or benzoyl groups react readily at -40°C with Grignard reagents to afford the corresponding alkyl or aryl thioglycosides in good yields. Monosaccharide derivatives having the SCN grouping at other positions form under similar conditions thioethers. Axial thiocyanates do not react. Elevated temperatures induce side reactions leading to mercaptans.
