57282-89-0

Upstream product

• 13096-62-3 (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one 
• 615275-19-9 (2R,3R,4R,5S,6S)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-(2,6-dimethoxy-phenyl)-tetrahydro-pyran 
• 2785-97-9 (2,6-dimethoxyphenyl)lithium 
• 108-24-7 acetic anhydride 
• 57282-87-8 β-D-glucopyranosyl-2,6-dimethoxybenzene 

Downstream Products

• 615275-33-7 Acetic acid (2S,3S,4R,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-(3-acetyl-2-hydroxy-6-methoxy-phenyl)-tetrahydro-pyran-3-yl ester 
• 615275-38-2 (E)-1-[2-Hydroxy-4-methoxy-3-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-phenyl]-3-(4-methoxy-phenyl)-propenone 
• 13037-90-6 1-[2-Hydroxy-4-methoxy-3-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-phenyl]-ethanone 

Relevant academic research and scientific papers

Constituents of Pterocarpus marsupium: An ayurvedic crude drug

Five new flavonoid C-glucosides, 6-hydroxy-2-(4-hydroxybenzyl)-benzofuran- 7-C-β-D-glucopyranoside (1), 3-(α-methoxy-4-hydroxybenzylidene)-6- hydroxybenzo-2(3H)-furanone-7-C-β-D-glucopyranoside (2), 2-hydroxy-2-p-hydroxybenzyl-3(2H)-6-hydroxybenzofuranone-7-C-β-D- glucopyranoside (4), 8-(C-β-D-glucopyranosyl)-7,3′,4′- trihydroxyflavone (5) and 1,2-bis(2,4-dihydroxy,3-C-glucopyranosyl)-ethanedione (6) and two known compounds C-β-D-glucopyranosyl-2,6-dihydroxyl benzene (7) and sesquiterpene (8), were isolated from an aqueous extract of the heartwood of Pterocarpus marsupium. The structure has been established using spectroscopic data.

Total synthesis of puerarin, an isoflavone C-glycoside

We completed the first total synthesis of puerarin (1), an isoflavone C-glycoside. The key intermediate, β-D-glucopyranosyl-2,6-dimethoxybenzene (9), was obtained by coupling of a lithiated aromatic reagent (3) with pyranolactone (2) in 56% yield. Condensation of (16) with p-methoxybenzaldehyde gave the chalcone (17). The protected chalcone (18) was cyclized to (19) in the presence of Tl(NO3)3. Demethylation of (19) was accomplished by refluxing with TMSI in CH3CN to give puerarin (1).

1-(2′, 6′-dihydroxyphenyl)-β-D-glucopyranoside, a novel C-glycoside from Pterocarpus marsupium

Isolation and characterization of a novel C-glycoside from Pterocarpus marsupium Roxb. (Leguminosae) is reported. The isolate coded as VS002 1, has been characterized as 1-(2κ, 6κ-dihydroxyphenyl)-β-D-glucopyranoside on the basis of spectroscopic data and derivatisation.