132817-37-9

Upstream product

• 634-36-6 1,2,3-trimethoxybenzene 
• 129889-18-5 2,3,4,6-Tetra-O-benzyl-β-D-glucopyranosyl trifluoroacetate 
• 1585169-36-3 C₄₃H₄₅BrO₈ 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 141196-74-9 1-trifluoroacetoxy-2,3,4,6-tetra-O-benzyl-α,β-D-glucopyranoside 

Downstream Products

• 132817-38-0 (2R,3S,4R,5R,6S)-2-Hydroxymethyl-6-(2,3,4-trimethoxy-phenyl)-tetrahydro-pyran-3,4,5-triol 
• 1585169-37-4 C₄₄H₄₆O₉ 
• 1585169-36-3 C₄₃H₄₅BrO₈ 
• 1585169-38-5 C₄₃H₄₄O₉ 
• 1585169-39-6 C₅₀H₅₀O₉ 
• 1585169-40-9 C₅₀H₅₀O₁₀ 
• 132817-45-9 2,3,4-Trimethoxy-1-phenylsulfinyl-5-(2,3,4,6-tetra-O-methoxycarbonyl-β-D-glucopyranosyl)benzene 
• 132817-44-8 2,3,4-Trimethoxy-1-phenylthio-5-(2,3,4,6-tetra-O-methoxycarbonyl-β-D-glucopyranosyl)benzene 
• 132817-41-5 1,2,3-Trimethoxy-4-methoxycarbonyl-6-(2,3,4,6-tetra-O-methoxycarbonyl-β-D-glucopyranosyl)benzene 
• 132817-40-4 1-Bromo-2,3,4-trimethoxy-5-(2,3,4,6-tetra-O-methoxycarbonyl-β-D-glucopyranosyl)benzene 
• 132817-39-1 1,2,3-Trimethoxy-4-(2,3,4,6-tetra-O-methoxycarbonyl-β-D-glucopyranosyl)benzene 
• 132817-43-7 1,2,3-Trimethoxy-4-methoxycarbonyl-6-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)benzene 
• 132817-42-6 2,3,4-Trimethoxy-5-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-benzoic acid methyl ester 

Relevant academic research and scientific papers

Synthesis of 3,3′-Di- O -methyl ardimerin and exploration of its DNA binding properties

The 3,3′-di-O-methyl derivative (15) of the bis-C-aryl glycoside natural product ardimerin (1) has been synthesized in 11 steps from 2,3,4,6-tetrabenzylglucose (2) and 1,2,3-trimethoxybenzene (3). Key steps in the synthesis involve a Lewis acid mediated Friedel-Crafts type glycosylation and a Yamaguchi lactonization under Yonemitsu conditions. 3,3′-Di-O-methyl ardimerin aggregates in aqueous solutions at concentrations greater than 1 M, and both UV and fluorescence binding studies indicate that 15 has a low affinity for duplex DNA.

Synthesis of bergenin-type C-glucosylarenes

Reaction of 1,2,3-trimethoxybenzene with 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl trifluoroacetate (5) in the presence of BF3*OEt2 afforded the 4-β-C-glycosylarene 6.Hydrogenolysis of 6, then O-methoxycarbonylation, and bromination gave 1-bromo-2,3,4-tri