[3R,4R,5R,6R]-4-[(tert-butyldimethylsilyl)oxy]-6-[(3,4-dimethoxybenzyl)oxy]-3,5-dimethylhept-1-ene

Base Information

• Chemical Name: [3R,4R,5R,6R]-4-[(tert-butyldimethylsilyl)oxy]-6-[(3,4-dimethoxybenzyl)oxy]-3,5-dimethylhept-1-ene
• CAS No.: 443283-14-5
• Molecular Formula: C₂₄H₄₂O₄Si
• Molecular Weight: 422.681
• Mol file: 443283-14-5.mol

Synonyms:[3R,4R,5R,6R]-4-[(tert-butyldimethylsilyl)oxy]-6-[(3,4-dimethoxybenzyl)oxy]-3,5-dimethylhept-1-ene

Chemical Property of [3R,4R,5R,6R]-4-[(tert-butyldimethylsilyl)oxy]-6-[(3,4-dimethoxybenzyl)oxy]-3,5-dimethylhept-1-ene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [3R,4R,5R,6R]-4-[(tert-butyldimethylsilyl)oxy]-6-[(3,4-dimethoxybenzyl)oxy]-3,5-dimethylhept-1-ene

There total 7 articles about [3R,4R,5R,6R]-4-[(tert-butyldimethylsilyl)oxy]-6-[(3,4-dimethoxybenzyl)oxy]-3,5-dimethylhept-1-ene 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: 98.0%

t-butyldimethylsiyl triflate (69739-34-0) + [3R,4R,5S,6R]-6-[(3,4-dimethoxybenzyl)oxy]-3,5-dimethylhept-1-en-4-ol (443283-30-5) → [3R,4R,5R,6R]-4-[(tert-butyldimethylsilyl)oxy]-6-[(3,4-dimethoxybenzyl)oxy]-3,5-dimethylhept-1-ene (443283-14-5)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at -40 ℃; for 0.5h;

DOI:10.1021/jo016413f

Reference yield:

ethyl anti-(2R,3R)-2-methyl-3-hydroxybutanoate (27372-03-8,51898-35-2,51898-36-3,63647-69-8,78088-27-4,78088-28-5,86853-34-1,92282-67-2,86853-33-0) → [3R,4R,5R,6R]-4-[(tert-butyldimethylsilyl)oxy]-6-[(3,4-dimethoxybenzyl)oxy]-3,5-dimethylhept-1-ene (443283-14-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 94 percent / lithium aluminum hydride / diethyl ether / 1 h

2: 84 percent / p-toluenesulfonic acid / benzene / 2 h / Heating

3: 98 percent / DIBAL-H / CH₂Cl₂ / 2.5 h / 0 °C

4: 9.8 g / oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / 0.17 h / 0 °C

5: 9.98 g / toluene / -78 °C

6: 98 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / -40 °C

With 2,6-dimethylpyridine; lithium aluminium tetrahydride; oxalyl dichloride; diisobutylaluminium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; In diethyl ether; dichloromethane; toluene; benzene; 4: Swern oxidation;

DOI:10.1021/jo016413f

Reference yield:

[2R,3R]-3-[(3,4-dimethoxybenzyl)oxy]-2-methylbutan-1-al (443283-13-4) → [3R,4R,5R,6R]-4-[(tert-butyldimethylsilyl)oxy]-6-[(3,4-dimethoxybenzyl)oxy]-3,5-dimethylhept-1-ene (443283-14-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 9.98 g / toluene / -78 °C

2: 98 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / -40 °C

With 2,6-dimethylpyridine; In dichloromethane; toluene;

DOI:10.1021/jo016413f

upstream raw materials:

t-butyldimethylsiyl triflate

(S,S)-diisopropyl tartrate (E)-crotylboronate

[2R,3R]-3-[(3,4-dimethoxybenzyl)oxy]-2-methylbutan-1-al

[3R,4R,5S,6R]-6-[(3,4-dimethoxybenzyl)oxy]-3,5-dimethylhept-1-en-4-ol

Downstream raw materials:

[2S,3S,4R,5R]-3-[(tert-butyldimethylsilyl)oxy]-5-[(3,4-dimethoxybenzyl)oxy]-2,4-dimethylhexan-1-al

[3S,4R,5R,6R,7R,8R]-6-[(tert-butyldimethylsilyl)oxy]-8-[(3,4-dimethoxybenzyl)oxy]-5,7-dimethyl-3-methoxynon-1-en-4-ol

[3S,4R,5R,6S,7R,8R]-6-[(tert-butyldimethylsilyl)oxy]-8-[(3,4-dimethoxybenzyl)oxy]-5,7-dimethyl-3-methoxy-4-[(methoxymethyl)oxy]non-1-ene

[3R,4S,5S,8S,9R,10R,11R,12S]-9-[(tert-butyldimethylsilyl)oxy]-12-methoxy-3-[(4-methoxybenzyl)oxy]-11-[(methoxymethyl)oxy]-2,4,8,10-tetramethyltetradec-13-en-5-ol-7-one