916494-82-1

Upstream product

• 108-24-7 acetic anhydride 
• 84954-92-7 cinnamyl 6-O-(α-L-arabinopyranosyl)-β-D-glucopyranoside 
• 916494-81-0 2,3,4-tri-O-acetyl-α-L-arabinopyranosyl-(1->6')-(2',3',4'-tri-O-acetyl-β-methyl-1'-thio-D-glucopyranoside) 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 1083195-64-5 ethyl 2,3,4-tri-O-acetyl-1-thio-β-D-glucopyranoside 
• 869848-87-3 2,3,4-tri-O-acetyl-α/β-L-arabinopyranosyl trichloroacetimidate 
• 14260-08-3 2,3,4-tri-O-acetyl-α-L-arabinopyranosyl-(1->6')-(1',2',3',4'-tetra-O-acetyl-β-D-glucopyranoside) 

Downstream Products

• 84954-92-7 cinnamyl 6-O-(α-L-arabinopyranosyl)-β-D-glucopyranoside 

Relevant academic research and scientific papers

Synthesis of the Rhodiola rosea glycoside rosavin

A synthetic scheme was proposed for the glycoside rosavin that includes a one-step glycosylation of cinnamyl alcohol with a disaccharide. The structure of the product was confirmed by PMR and 13C NMR spectroscopy.

Synthetic method of rosavin

The present invention provides a synthetic method of rosavin. The method comprises the following steps: in a protective atmosphere and under presence of a water-removing agent, trimethylsilyl trifluoromethanesulfonate catalyzes 2,3,4-tri-O-acetyl-L-arabinofuranoside trichloroacetimide ester and ethyl 2,3,4-tri-O-acetyl-beta-D-thioglucopyranoside to react in an organic solvent, then beta-(E)-cinnamyl alcohol, NIS and TfOH are added in sequence to continue the reaction to completion, a reaction quencher is added, a crude intermediate is obtained by isolation, and then the crude intermediate reacts with sodium methoxide in methanol to separate and purify the rosavin. Commercial L-arabinose donor, D-glucose acceptor and beta-(E)-cinnamyl alcohol are used as raw materials to obtain a high-purity rosavin product through a three-step reaction, the intermediate does not need to be purified and a final product is obtained through crystallization with a total yield of 70% or more. The method isclean in reaction system, the product can be directly crystallized and separated from the system, the product has high yield and high purity, and the method is beneficial to large-scale industrializedpreparation of the rosavin.

GLYCOSIDES OF CINNAMYL ALCOHOL FROM THE RHIZOMES OF Rhodiola rosea

Three new cinnamyl alcohol glycosides have been isolated for the first time from the rhizomes of roseroot stonecrop Rhodiola rosea L. (Sedum rosea).On the basis of chemical transformations and the results of UV, IR, PMR, and mass spectroscopy the following structures are proposed for the compounds isolated: rozin - trans-cinnamyl O-β-D-glucopyranoside; rozavin - trans-cinnamyl O-(6'-O-α-L-arabinopyranosyl-β-D-glucopyranoside); and rozarin - trans-cinnamyl O-(6'-O-α-L-arabinofuranosyl-β-D-glucopyranoside).