109984-83-0

Basic information

• Product Name: Silane, [[3-methoxy-6-[2-(3,4,5-trimethoxyphenyl)ethenyl]-1,2-phenylene]bis(oxy )]bis[(1,1-dimethylethyl)dimethyl-, (E)-
• CAS NO: 109984-83-0
• Molecular Formula: C30H48O6Si2
• Molecular Weight: 560.879
• Mol File: 109984-83-0.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Silane, [[3-methoxy-6-[2-(3,4,5-trimethoxyphenyl)ethenyl]-1,2-phenylene]bis(oxy )]bis[(1,1-dimethylethyl)dimethyl-, (E)-(CAS DataBase Reference)
• NIST Chemistry Reference: Silane, [[3-methoxy-6-[2-(3,4,5-trimethoxyphenyl)ethenyl]-1,2-phenylene]bis(oxy )]bis[(1,1-dimethylethyl)dimethyl-, (E)-(109984-83-0)
• EPA Substance Registry System: Silane, [[3-methoxy-6-[2-(3,4,5-trimethoxyphenyl)ethenyl]-1,2-phenylene]bis(oxy )]bis[(1,1-dimethylethyl)dimethyl-, (E)-(109984-83-0)

Safety Data

• Hazardous Substances Data: 109984-83-0(Hazardous Substances Data)

Upstream product

• 109971-66-6 2,3-bis<(tert-butyldimethylsilyl)oxy>-4-methoxybenzaldehyde 
• 108683-61-0 triphenyl(3,4,5-trimethoxybenzyl)phosphonium chloride 
• 1116460-26-4 {2,3-di[(tert-butyldimethylsilyl)oxy]-4-methoxybenzyl}triphenylphosphonium bromide 
• 86-81-7 3,4,5-trimethoxy-benzaldehyde 
• 3840-30-0 5-(chloromethyl)-1,2,3-trimethoxybenzene 

Downstream Products

• 309947-17-9 (+/-)-2-(2',3'-di[(tert-butyldimethylsilyl)oxy]-4'-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)acetaldehyde 
• 290295-01-1 (1S,2S)-1,2-dihydroxy-1-[2',3'-di(tert-butyldimethylsilyloxy)-4'-methoxyphenyl]-2-(3'',4'',5''-trimethoxyphenyl)ethane 

Relevant articles and documents

Development of synthetic methodology suitable for the radiosynthesis of combretastatin A-1 (CA1) and its corresponding prodrug CA1P

Synthetic methodology has been established suitable for the preparation of combretastatin A-1 (CA1) and its corresponding phosphate prodrug salt (CA1P) in high specific activity radiolabeled form. Judicious selection of appropriate phenolic protecting groups to distinguish positions on the A-ring from the B-ring of the stilbenoid was paramount for the success of this project. Methylation of the C-4' phenolic moiety by removal of the tert- butyldimethylsilyl protecting group in the presence of methyl iodide was accomplished in excellent yield without significant Z to E isomerization. This step (carried out with 12C-methyl iodide as proof of concept in this study) represents the process in which a 14C radioisotope could be incorporated in an actual radiosynthesis. CA1 is a natural product isolated from the African bush willow tree (Combretum caffrum) that has important medicinal value due, in part, to its ability to inhibit tubulin assembly. As a prodrug, CA1P (OXi4503) is in human clinical trials as a vascular disrupting agent.

Synthesis of biologically active polyphenolic glycosides (combretastatin and resveratrol series)

(E)-3-(β-D-Glucopyranosyloxy)-4',5-dihydroxystilbene (resveratrol 3-β-D-glucoside, piceid), (Z)-2',3'-dihydroxy-3,4,4',5-tetramethoxystilbene (combretastatin A-1), (Z)-3'-hydroxy-3,4,4', 5-tetramethoxystilbene (combretastatin A-4), (Z)-2'-hydroxy-3,4,4',5-tetramethoxystilbene (combretastatin iso-A-4), α,β-dihydro-2',3'-dihydroxy-3,4,4',5-tetramethoxystilbene (combretastatin B-1), the corresponding glucosides, and related compounds have been synthesized via Wittig reactions followed by,glucosylation under phase-transfer catalysis. Most of the compounds synthesized have been tested with respect to biological activity (cytostatic, cytotoxic, antimitotic, neurotoxic, antiplatelet aggregation activity).