62502-04-9

Upstream product

• 2628-16-2 p-acetoxystyrene 
• 709030-17-1 3-acetoxy-5-iodophenyl-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 108-24-7 acetic anhydride 
• 27208-80-6 polydatin 
• 709030-16-0 (3-hydroxy-5-iodophenyl) 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 64339-43-1 5-iodoresorcinol 

Downstream Products

• 27208-80-6 polydatin 
• 29884-49-9 (E)-astringin 

Relevant academic research and scientific papers

Short-step syntheses of naturally occurring polyoxygenated aromatics based on site-selective transformation

Wogonin and astringin were synthesized from inexpensive chrysin and piceid in short steps. The key feature of these syntheses is site-selective transformation. The target molecules were obtained in 27 and 62% yields from the starting materials, respectively.

Synthesis of acacetin and resveratrol 3,5-di-O-β-glucopyranoside using lipase-catalyzed regioselective deacetylation of polyphenol glycoside peracetates as the key step

Acacetin and resveratrol 3,5-di-O-β-glucopyranoside were synthesized from naturally abundant naringin and piceid in 65% and 62% overall yield, respectively. The key steps were the regioselective deacetylation of the peracetates of the glycosylated forms with Candida antarctica lipase B (Novozym 435) and Burkholderia cepacia lipase (Amano PS-IM). Deacetylation occurred exclusively at the least hindered position of the aromatic moieties and all acetyl groups in the sugar side chain remained intact. This excellent selectivity enabled regiospecific transformation of the liberated phenolic hydroxy groups, resulting in efficient synthesis of the target molecules.

A novel, convenient synthesis of the 3-O-β-D- and 4′-O-β -D-glucopyranosides of trans-resveratrol

trans-Resveratrol-3-O-β-D-glucupyranoside (trans-piceid, 2) and trans-resveratrol-4′-O-β-D-glucupyranoside (trans-resveratroloside 3) are the naturally occurring O-glucoside conjugates of the polyphenolic stilbenoid trans-resveratrol 1. Recently, attention has been drawn towards the interesting biological properties of the glucoside conjugates 2 and 3 as well as those of the aglycone 1. The fact that only limited quantities can be obtained by extraction from natural sources has prompted the development of novel syntheses of 2 and 3, based on a convergent Heck-coupling strategy, which now conveniently allows for the preparation of multi-milligram to gram quantities of each.