methyl ({(1R)-2-{[tert-butyl(diphenyl)silyl]oxy}-1-[(phenylseleno)methyl]ethyl}oxy)acetate

Base Information

• Chemical Name: methyl ({(1R)-2-{[tert-butyl(diphenyl)silyl]oxy}-1-[(phenylseleno)methyl]ethyl}oxy)acetate
• CAS No.: 936251-82-0
• Molecular Formula: C₂₈H₃₄O₄SeSi
• Molecular Weight: 541.621
• Mol file: 936251-82-0.mol

Synonyms:methyl ({(1R)-2-{[tert-butyl(diphenyl)silyl]oxy}-1-[(phenylseleno)methyl]ethyl}oxy)acetate

Chemical Property of methyl ({(1R)-2-{[tert-butyl(diphenyl)silyl]oxy}-1-[(phenylseleno)methyl]ethyl}oxy)acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl ({(1R)-2-{[tert-butyl(diphenyl)silyl]oxy}-1-[(phenylseleno)methyl]ethyl}oxy)acetate

There total 3 articles about methyl ({(1R)-2-{[tert-butyl(diphenyl)silyl]oxy}-1-[(phenylseleno)methyl]ethyl}oxy)acetate 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: 74.0%

bromoacetic acid methyl ester (96-32-2) + (2R)-1-{[tert-butyl(diphenyl)silyl]oxy}-3-(phenylseleno)propan-2-ol (702711-07-7) → methyl ({(1R)-2-{[tert-butyl(diphenyl)silyl]oxy}-1-[(phenylseleno)methyl]ethyl}oxy)acetate (936251-82-0)

Guidance literature:

(2R)-1-{[tert-butyl(diphenyl)silyl]oxy}-3-(phenylseleno)propan-2-ol; With sodium hydride; In benzene; at 20 ℃; for 1h;

bromoacetic acid methyl ester; With 15-crown-5; In benzene; at 40 ℃; Further stages.;

DOI:10.1016/j.tet.2007.04.047

Reference yield:

diphenyl diselenide (1666-13-3) → methyl ({(1R)-2-{[tert-butyl(diphenyl)silyl]oxy}-1-[(phenylseleno)methyl]ethyl}oxy)acetate (936251-82-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: NaBH₄ / ethanol / 0.5 h / 20 - 40 °C

1.2: 93 percent / ethanol / 6 h

2.1: 98 percent / imidazole / dimethylformamide / 4 h / 20 °C

3.1: NaH / benzene / 1 h / 20 °C

3.2: 74 percent / 15-crown-5 / benzene / 40 °C

With 1H-imidazole; sodium tetrahydroborate; sodium hydride; In ethanol; N,N-dimethyl-formamide; benzene;

DOI:10.1016/j.tet.2007.04.047

Reference yield:

(2R)-3-(phenylseleno)propane-1,2-diol (744198-92-3) → methyl ({(1R)-2-{[tert-butyl(diphenyl)silyl]oxy}-1-[(phenylseleno)methyl]ethyl}oxy)acetate (936251-82-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 98 percent / imidazole / dimethylformamide / 4 h / 20 °C

2.1: NaH / benzene / 1 h / 20 °C

2.2: 74 percent / 15-crown-5 / benzene / 40 °C

With 1H-imidazole; sodium hydride; In N,N-dimethyl-formamide; benzene;

DOI:10.1016/j.tet.2007.04.047

upstream raw materials:

bromoacetic acid methyl ester

(2R)-1-{[tert-butyl(diphenyl)silyl]oxy}-3-(phenylseleno)propan-2-ol

diphenyl diselenide

(2R)-3-(phenylseleno)propane-1,2-diol

Downstream raw materials:

({(1R)-2-{[tert-butyl(diphenyl)silyl]oxy}-1-[(phenylseleno)methyl]ethyl}oxy)acetaldehyde

(3R,5S)-5-({[tert-butyl(diphenyl)silyl]oxy}methyl)tetrahydrofuran-3-ol

(3S,5S)-5-({[tert-butyl(diphenyl)silyl]oxy}methyl)tetrahydrofuran-3-ol