(-)-(3R,4R)-4-[tert-butyl(diphenyl)silyl]oxy-6-[(4-methoxybenzyl)oxy]-3-methyl-1-hexanol

Base Information

• Chemical Name: (-)-(3R,4R)-4-[tert-butyl(diphenyl)silyl]oxy-6-[(4-methoxybenzyl)oxy]-3-methyl-1-hexanol
• CAS No.: 862995-08-2
• Molecular Formula: C₃₁H₄₂O₄Si
• Molecular Weight: 506.758
• Mol file: 862995-08-2.mol

Synonyms:(-)-(3R,4R)-4-[tert-butyl(diphenyl)silyl]oxy-6-[(4-methoxybenzyl)oxy]-3-methyl-1-hexanol

Chemical Property of (-)-(3R,4R)-4-[tert-butyl(diphenyl)silyl]oxy-6-[(4-methoxybenzyl)oxy]-3-methyl-1-hexanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-(3R,4R)-4-[tert-butyl(diphenyl)silyl]oxy-6-[(4-methoxybenzyl)oxy]-3-methyl-1-hexanol

There total 5 articles about (-)-(3R,4R)-4-[tert-butyl(diphenyl)silyl]oxy-6-[(4-methoxybenzyl)oxy]-3-methyl-1-hexanol 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: 78.0%

(+)-(3R,4R)-1-[(4-methoxybenzyl)oxy]-4-methyl-3-(tert-butyldiphenylsilyloxy)-5-hexene (862995-07-1) → (-)-(3R,4R)-4-[tert-butyl(diphenyl)silyl]oxy-6-[(4-methoxybenzyl)oxy]-3-methyl-1-hexanol (862995-08-2)

Guidance literature:

(+)-(3R,4R)-1-[(4-methoxybenzyl)oxy]-4-methyl-3-(tert-butyldiphenylsilyloxy)-5-hexene; With dimethylsulfide borane complex; In tetrahydrofuran; at 20 ℃;

With sodium hydroxide; dihydrogen peroxide; In tetrahydrofuran;

DOI:10.1021/ol051260u

Reference yield:

3-(p-methoxybenzyloxy)propanal (128461-65-4) → (-)-(3R,4R)-4-[tert-butyl(diphenyl)silyl]oxy-6-[(4-methoxybenzyl)oxy]-3-methyl-1-hexanol (862995-08-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: BF₃*OEt₂ / tetrahydrofuran / 2 h / -78 °C

1.2: 1.90 g / aq. NaOH; H₂O₂ / tetrahydrofuran / 1 h / Heating

2.1: 99 percent / imidazole / dimethylformamide / 100 °C

3.1: BH₃*DMS / tetrahydrofuran / 6 h / 20 °C

3.2: 78 percent / NaOH; aq. H₂O₂ / tetrahydrofuran; methanol / 3 h / 20 °C

With 1H-imidazole; dimethylsulfide borane complex; boron trifluoride diethyl etherate; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1039/b604334h

Reference yield:

3-(4-methoxybenzyl)oxypropan-1-ol (135362-69-5) → (-)-(3R,4R)-4-[tert-butyl(diphenyl)silyl]oxy-6-[(4-methoxybenzyl)oxy]-3-methyl-1-hexanol (862995-08-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 96 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

2.1: BF₃*OEt₂ / tetrahydrofuran / 2 h / -78 °C

2.2: 1.90 g / aq. NaOH; H₂O₂ / tetrahydrofuran / 1 h / Heating

3.1: 99 percent / imidazole / dimethylformamide / 100 °C

4.1: BH₃*DMS / tetrahydrofuran / 6 h / 20 °C

4.2: 78 percent / NaOH; aq. H₂O₂ / tetrahydrofuran; methanol / 3 h / 20 °C

With 1H-imidazole; oxalyl dichloride; dimethylsulfide borane complex; boron trifluoride diethyl etherate; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1039/b604334h

upstream raw materials:

(+)-(3R,4R)-1-[(4-methoxybenzyl)oxy]-4-methyl-3-(tert-butyldiphenylsilyloxy)-5-hexene

3-(p-methoxybenzyloxy)propanal

3-(4-methoxybenzyl)oxypropan-1-ol

tert-butylchlorodiphenylsilane

Downstream raw materials:

(+)-(3R,4R)-4-[tert-butyl(diphenyl)silyl]oxy-6-[(4-methoxybenzyl)oxy]-3-methylhexanal