4-methoxybenzyl {(1R)-1-[(R)-{[tert-butyl(dimethyl)silyl]oxy}(phenyl)methyl]pent-4-yn-1-yl}carbamate

Base Information

• Chemical Name: 4-methoxybenzyl {(1R)-1-[(R)-{[tert-butyl(dimethyl)silyl]oxy}(phenyl)methyl]pent-4-yn-1-yl}carbamate
• CAS No.: 1190391-64-0
• Molecular Formula: C₂₇H₃₇NO₄Si
• Molecular Weight: 467.681
• Mol file: 1190391-64-0.mol

Synonyms:4-methoxybenzyl {(1R)-1-[(R)-{[tert-butyl(dimethyl)silyl]oxy}(phenyl)methyl]pent-4-yn-1-yl}carbamate

Chemical Property of 4-methoxybenzyl {(1R)-1-[(R)-{[tert-butyl(dimethyl)silyl]oxy}(phenyl)methyl]pent-4-yn-1-yl}carbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-methoxybenzyl {(1R)-1-[(R)-{[tert-butyl(dimethyl)silyl]oxy}(phenyl)methyl]pent-4-yn-1-yl}carbamate

There total 12 articles about 4-methoxybenzyl {(1R)-1-[(R)-{[tert-butyl(dimethyl)silyl]oxy}(phenyl)methyl]pent-4-yn-1-yl}carbamate 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: 91.0%

(R)-2-((S)-phenyl((trimethylsilyl)oxy)methyl)hex-5-ynoic acid (1190391-63-9) + 4-Methoxybenzyl alcohol (105-13-5) → 4-methoxybenzyl {(1R)-1-[(R)-{[tert-butyl(dimethyl)silyl]oxy}(phenyl)methyl]pent-4-yn-1-yl}carbamate (1190391-64-0)

Guidance literature:

(R)-2-((S)-phenyl((trimethylsilyl)oxy)methyl)hex-5-ynoic acid; With diphenyl phosphoryl azide; triethylamine; In toluene; at 25 ℃; for 5h; Inert atmosphere;

4-Methoxybenzyl alcohol; In toluene; at 80 - 110 ℃; for 13h; Inert atmosphere;

DOI:10.1021/jm4017224

Reference yield:

hex-5-ynoic acid (53293-00-8) → 4-methoxybenzyl {(1R)-1-[(R)-{[tert-butyl(dimethyl)silyl]oxy}(phenyl)methyl]pent-4-yn-1-yl}carbamate (1190391-64-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: triethylamine; pivaloyl chloride / tetrahydrofuran / 2.33 h / -25 °C / Inert atmosphere

1.2: 12 h / 20 °C / Cooling; Inert atmosphere

2.1: chloro-trimethyl-silane; triethylamine; magnesium chloride / ethyl acetate / 72 h / 20 °C / Inert atmosphere

2.2: 5 h / 20 °C / Inert atmosphere

3.1: lithium hydroxide; dihydrogen peroxide / water; tetrahydrofuran / 3 h / 0 - 5 °C / Inert atmosphere

3.2: 0 - 5 °C

3.3: 0 °C / pH 3

4.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 4.17 h / 20 °C / Inert atmosphere

5.1: triethylamine; diphenyl phosphoryl azide / toluene / 5 h / 20 °C / Inert atmosphere

5.2: 16 h / 105 °C / Inert atmosphere

With chloro-trimethyl-silane; diphenyl phosphoryl azide; dihydrogen peroxide; pivaloyl chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; magnesium chloride; lithium hydroxide; In tetrahydrofuran; water; ethyl acetate; toluene; acetonitrile;

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → 4-methoxybenzyl {(1R)-1-[(R)-{[tert-butyl(dimethyl)silyl]oxy}(phenyl)methyl]pent-4-yn-1-yl}carbamate (1190391-64-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 4.17 h / 20 °C / Inert atmosphere

2.1: triethylamine; diphenyl phosphoryl azide / toluene / 5 h / 20 °C / Inert atmosphere

2.2: 16 h / 105 °C / Inert atmosphere

With diphenyl phosphoryl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In toluene; acetonitrile;

upstream raw materials:

(R)-2-((S)-phenyl((trimethylsilyl)oxy)methyl)hex-5-ynoic acid

4-Methoxybenzyl alcohol

tert-butyldimethylsilyl chloride

hex-5-ynoic acid

Downstream raw materials:

4-methoxybenzyl [(1R)-1-[(R)-{[tert-butyl(dimethyl)silyl]oxy}(phenyl)methyl]-5-(4-nitrophenyl)pent-4-yn-1-yl]carbamate

C₃₃H₄₀BrNO₄Si

tert-butyl (2R,5S)-2-[(R)-hydroxy(phenyl)methyl]-5-[4-({[(3-phenyl-1H-1,2,4-triazol-5-yl)methyl]amino}carbonyl)benzyl]pyrrolidine-1-carboxylate

tert-butyl (2R,5S)-2-[(R)-{[tert-butyl(dimethyl)silyl]oxy}(phenyl)methyl]-5-[4-[methyl(pyridine-3-ylmethyl)carbamoyl]benzyl]pyrrolidine-1-carboxylate