5-<(tert-butyldimethylsilyl)oxy>-(+/-)-combretastatin

Base Information

• Chemical Name: 5-<(tert-butyldimethylsilyl)oxy>-(+/-)-combretastatin
• CAS No.: 97315-17-8
• Molecular Formula: C₂₄H₃₆O₆Si
• Molecular Weight: 448.632
• Mol file: 97315-17-8.mol

Synonyms:5-<(tert-butyldimethylsilyl)oxy>-(+/-)-combretastatin

Chemical Property of 5-<(tert-butyldimethylsilyl)oxy>-(+/-)-combretastatin

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-<(tert-butyldimethylsilyl)oxy>-(+/-)-combretastatin

There total 5 articles about 5-<(tert-butyldimethylsilyl)oxy>-(+/-)-combretastatin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 60.0%

3,4,5-trimethoxy-benzaldehyde (86-81-7) + 3-<(tert-butyldimethylsilyl)oxy>-4-methoxybenzyl bromide (97315-20-3) → 5-<(tert-butyldimethylsilyl)oxy>-(+/-)-combretastatin (97315-17-8)

Guidance literature:

With lithium; In tetrahydrofuran; for 3h; ultrasound;

DOI:10.1021/jo00218a032

Reference yield:

isovanillin (621-59-0) → 5-<(tert-butyldimethylsilyl)oxy>-(+/-)-combretastatin (97315-17-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 95 percent / diisopropylethylamine / dimethylformamide / 1 h / Ambient temperature

2: 85 percent / NaBH₄ / ethanol / 0.5 h

3: 65 percent / trimethylsilyl chloride, lithium bromide / acetonitrile / 1 h

4: 60 percent / Li / tetrahydrofuran / 3 h / ultrasound

With sodium tetrahydroborate; chloro-trimethyl-silane; lithium; N-ethyl-N,N-diisopropylamine; lithium bromide; In tetrahydrofuran; ethanol; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jo00218a032

Reference yield:

3-<(tert-butyldimethylsilyl)oxy>-4-methoxybenzyl alkohol (97315-19-0) → 5-<(tert-butyldimethylsilyl)oxy>-(+/-)-combretastatin (97315-17-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 65 percent / trimethylsilyl chloride, lithium bromide / acetonitrile / 1 h

2: 60 percent / Li / tetrahydrofuran / 3 h / ultrasound

With chloro-trimethyl-silane; lithium; lithium bromide; In tetrahydrofuran; acetonitrile;

DOI:10.1021/jo00218a032

upstream raw materials:

3,4,5-trimethoxy-benzaldehyde

3-<(tert-butyldimethylsilyl)oxy>-4-methoxybenzyl bromide

isovanillin

3-<(tert-butyldimethylsilyl)oxy>-4-methoxybenzyl alkohol

Downstream raw materials:

5-[(2R)-2-hydroxy-2-(3,4,5-trimethoxyphenyl)ethyl]-2-methoxyphenol

5-<(tert-butyldimethylsilyl)oxy>-(-)-combretastatin

(-)-combretastatin