Methyl-((S)-1-(S)-oxiranyl-2-phenyl-ethyl)-carbamic acid tert-butyl ester

Base Information

• Chemical Name: Methyl-((S)-1-(S)-oxiranyl-2-phenyl-ethyl)-carbamic acid tert-butyl ester
• CAS No.: 238753-81-6
• Molecular Formula: C₁₆H₂₃NO₃
• Molecular Weight: 277.364
• Mol file: 238753-81-6.mol

Synonyms:Methyl-((S)-1-(S)-oxiranyl-2-phenyl-ethyl)-carbamic acid tert-butyl ester

Chemical Property of Methyl-((S)-1-(S)-oxiranyl-2-phenyl-ethyl)-carbamic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methyl-((S)-1-(S)-oxiranyl-2-phenyl-ethyl)-carbamic acid tert-butyl ester

There total 6 articles about Methyl-((S)-1-(S)-oxiranyl-2-phenyl-ethyl)-carbamic acid tert-butyl ester 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: 75.0%

di-tert-butyl dicarbonate (24424-99-5) + Methyl-((S)-1-(S)-oxiranyl-2-phenyl-ethyl)-amine (238753-80-5) → Methyl-((S)-1-(S)-oxiranyl-2-phenyl-ethyl)-carbamic acid tert-butyl ester (238753-81-6)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; at 20 ℃; for 2h;

DOI:10.1055/s-1999-2765

Reference yield:

(R,R)-3-(phenylmethyl)oxiranemethanol (78571-81-0,81096-89-1,85531-71-1,99883-80-4,128575-26-8,116949-62-3) → Methyl-((S)-1-(S)-oxiranyl-2-phenyl-ethyl)-carbamic acid tert-butyl ester (238753-81-6)

Guidance literature:

Multi-step reaction with 4 steps

1: Ti(iPrO)2(N₃)2 / benzene / 75 °C

2: 77 percent / H₂ / 10 percent Pd/C / ethyl acetate / 20 °C / 760 Torr

3: 75 percent / PPh₃; DEAD / CHCl₃ / Heating

4: NaH / tetrahydrofuran / 0 °C

With diisopropoxytitanium diazide; hydrogen; sodium hydride; triphenylphosphine; diethylazodicarboxylate; 10% palladium on active carbon; In tetrahydrofuran; chloroform; ethyl acetate; benzene; 1: Ring cleavage / 2: Hydrogenation / 3: Mitsunobu cyclization / 4: Methylation;

DOI:10.1016/S0040-4039(99)01953-X

Reference yield:

(2S,3S)-2-azido-1-phenyl-butane-3,4-diol (116949-67-8) → Methyl-((S)-1-(S)-oxiranyl-2-phenyl-ethyl)-carbamic acid tert-butyl ester (238753-81-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 77 percent / H₂ / 10 percent Pd/C / ethyl acetate / 20 °C / 760 Torr

2: 75 percent / PPh₃; DEAD / CHCl₃ / Heating

3: NaH / tetrahydrofuran / 0 °C

With hydrogen; sodium hydride; triphenylphosphine; diethylazodicarboxylate; 10% palladium on active carbon; In tetrahydrofuran; chloroform; ethyl acetate; 1: Hydrogenation / 2: Mitsunobu cyclization / 3: Methylation;

DOI:10.1016/S0040-4039(99)01953-X

upstream raw materials:

di-tert-butyl dicarbonate

Methyl-((S)-1-(S)-oxiranyl-2-phenyl-ethyl)-amine

(1-oxiranyl-2-phenylethyl)carbamic acid tert-butyl ester

methyl iodide

Downstream raw materials:

[1-benzyl-2-(tert-butyl-dimethyl-silanyloxy)-pent-4-enyl]-methyl-carbamic acid tert-butyl ester

((1S,2R)-1-Benzyl-2-methoxymethoxy-pent-4-enyl)-methyl-carbamic acid tert-butyl ester

[1-benzyl-2-(tert-butyl-dimethyl-silanyloxy)-3-cyano-propyl]-methyl-carbamic acid tert-butyl ester

(3R,4S)-4-(tert-Butoxycarbonyl-methyl-amino)-3-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-pentanoic acid

Refernces

• 1、 Catasus, Monica,Moyano, Albert,Pericas, Miquel A.,Riera, Antoni. "A totally stereocontrolled route to N-methyl-γ-amino-β-hydroxy acids: Asymmetric synthesis of the amino acid component of hapalosin". . p. 9309 - 9312. Retrieved 2007/10/03.