(3R,4S,5S)-1-[(tert-butyldiphenylsilyl)oxy]-2,4-dimethyl-3-[(para-methoxybenzyl)oxy]-5-hexene

Base Information

• Chemical Name: (3R,4S,5S)-1-[(tert-butyldiphenylsilyl)oxy]-2,4-dimethyl-3-[(para-methoxybenzyl)oxy]-5-hexene
• CAS No.: 502846-32-4
• Molecular Formula: C₃₂H₄₂O₃Si
• Molecular Weight: 502.769
• Mol file: 502846-32-4.mol

Synonyms:(3R,4S,5S)-1-[(tert-butyldiphenylsilyl)oxy]-2,4-dimethyl-3-[(para-methoxybenzyl)oxy]-5-hexene

Chemical Property of (3R,4S,5S)-1-[(tert-butyldiphenylsilyl)oxy]-2,4-dimethyl-3-[(para-methoxybenzyl)oxy]-5-hexene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4S,5S)-1-[(tert-butyldiphenylsilyl)oxy]-2,4-dimethyl-3-[(para-methoxybenzyl)oxy]-5-hexene

There total 1 articles about (3R,4S,5S)-1-[(tert-butyldiphenylsilyl)oxy]-2,4-dimethyl-3-[(para-methoxybenzyl)oxy]-5-hexene 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: 77.0%

O-(4-methoxybenzyl)-trichloroacetimidate (89238-99-3) + (2R,3S,4S)-1-(tert-Butyl-diphenyl-silanyloxy)-2,4-dimethyl-hex-5-en-3-ol → (3R,4S,5S)-1-[(tert-butyldiphenylsilyl)oxy]-2,4-dimethyl-3-[(para-methoxybenzyl)oxy]-5-hexene (502846-32-4)

Guidance literature:

With pyridinium p-toluenesulfonate; In dichloromethane; at 23 ℃; for 6h;

DOI:10.1021/jo0267908

Reference yield: 92.0%

(3R,4S,5S)-1-[(tert-butyldiphenylsilyl)oxy]-2,4-dimethyl-3-[(para-methoxybenzyl)oxy]-5-hexene (502846-32-4) → (2R,3R,4S)-1-[(tert-butyldiphenylsilyl)oxy]-2,4-dimethyl-3-[(para-methoxybenzyl)oxy]-5,6-hexanediol (502846-33-5)

Guidance literature:

With osmium(VIII) oxide; 4-methylmorpholine N-oxide; In tetrahydrofuran; water; tert-butyl alcohol; at 23 ℃;

DOI:10.1021/jo0267908

Reference yield:

(3R,4S,5S)-1-[(tert-butyldiphenylsilyl)oxy]-2,4-dimethyl-3-[(para-methoxybenzyl)oxy]-5-hexene (502846-32-4) → 1-[(tert-butyldiphenylsilyl)oxy]-5-hydroxy-3-[(para-methoxybenzyl)oxy]-2,4,6-trimethyloct-7-ene

Guidance literature:

Multi-step reaction with 3 steps

1: 92 percent / OsO₄; N-methylmorpholine N-oxide / tetrahydrofuran; H₂O; 2-methyl-propan-2-ol / 23 °C

2: NaIO₄ / tetrahydrofuran; H₂O / 1 h

3: i-Pr₂NEt / CH₂Cl₂ / 36 h / 0 °C

With sodium periodate; osmium(VIII) oxide; 4-methylmorpholine N-oxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; water; tert-butyl alcohol;

DOI:10.1021/jo0267908

upstream raw materials:

O-(4-methoxybenzyl)-trichloroacetimidate

Downstream raw materials:

(2R,3R,4S)-1-[(tert-butyldiphenylsilyl)oxy]-2,4-dimethyl-3-[(para-methoxybenzyl)oxy]-5,6-hexanediol

(2R,3R,4S,5S,6R)-1-[(tert-butyldiphenylsilyl)oxy]-2,4,6-trimethyl-3,5-dihydroxyoct-7-ene

(2R,3R,4R)-5-(tert-butyldiphenylsilyloxy)-3-(4-methoxybenzyloxy)-2,4-dimethylpentanal

(2R,3R,4S,5S,6R)-1-[(tert-butyldiphenylsilyl)oxy]-5-hydroxy-3-[(para-methoxybenzyl)oxy]-2,4,6-trimethyloct-7-ene