Total synthesis of phenylpropanoid glycosides, grayanoside A and syringalide B, through a common intermediate

Plantamajoside — A current review

“…In 2005, Li described complete synthesis of syringalide B, a phenylpropanoid monoglycoside (Li et al, 2005). Syringalide B was synthesized through a common intermediate, using a benzyl-moiety as a temporary protecting group following a shorter route together with another polyphenolic glycoside-grayanoside A (Das et al, 2007). The synthesis of arenarioside, a benzyl-protected analogue of a trisaccharide phenylpropanoid glycoside, was carried out by Zhou et al (2006).…”

Crystal Structure, Synthesis and Biological Activity of Ether and Ester <i>Trans</i>-Ferulic Acid Derivatives

“…1 Figure 1. 13 Methoxymethyl (E)-3-(4-hydroxy-3-methoxyphenyl)acrylate (2). To a solution of 1.0 meq of FA (0.1940 g) in 30 ml of CH 2 Cl 2 , 1.1 meq of triethylamine International Journal of Organic Chemistry and 1.1 meq of chloromethyl methyl ether (Cl-MOM) were added.…”

“…1 H NMR (500 MHz, chloroform-d); δ 7.68 (d, J = 15.9 Hz, 1H), 7.08 (m, 1H), 7.04 (d, J = 2.0 Hz, 1H), 6.92 (d, J = 8.2 Hz, 1H), 6.31 (d, J = 15.9 Hz, 1H), 6.00 (s, 1H), 5.37 (s, 2H), 3.93 (s, 3H), 3.52 (s, 3H) spectrum is shown in Figure 2. 13 Figure 3. 13 Methyl (E)-3-(4-(benzyloxy)-3-methoxyphenyl)acrylate (4).…”

“…13 Figure 3. 13 Methyl (E)-3-(4-(benzyloxy)-3-methoxyphenyl)acrylate (4). 1 meq of compound 1 was dissolved in 30 mL of anhydrous acetone and 1 meq of K 2 CO 3 and 1.1 meq of benzyl bromide were stirred at room temperature.…”

Short synthesis of the common trisaccharide core of kankanose and kankanoside isolated from Cistanche tubulosa

“…Therefore, development of concise chemical synthetic strategies would be the best option to gain access to these compounds on a large scale. A few reports are available in the literature for the synthesis of phenylethyl oligosaccharides [8–9]. In this context, we developed a synthetic strategy for the synthesis of the common trisaccharide core of kankanose, kankanoside F, H 1 , H 2 and I isolated from C. tubulosa thereby exploiting newly developed regio- and stereoselective glycosylation conditions (Fig.…”