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

Base Information

• Chemical Name: Methyl-((S)-1-(S)-oxiranyl-2-phenyl-ethyl)-carbamic acid benzyl ester
• CAS No.: 260562-76-3
• Molecular Formula: C₁₉H₂₁NO₃
• Molecular Weight: 311.381
• Mol file: 260562-76-3.mol

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

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

There total 5 articles about Methyl-((S)-1-(S)-oxiranyl-2-phenyl-ethyl)-carbamic acid benzyl 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: 69.0%

N-benzyloxycarbonyl-3(S)-amino-1,2(S)epoxy-4-phenylbutane (128018-44-0) + methyl iodide (74-88-4) → Methyl-((S)-1-(S)-oxiranyl-2-phenyl-ethyl)-carbamic acid benzyl ester (260562-76-3)

Guidance literature:

With sodium hydride; In tetrahydrofuran; at 0 ℃;

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

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 benzyl ester (260562-76-3)

Guidance literature:

Multi-step reaction with 5 steps

1: Ti(iPrO)2(N₃)2 / benzene / 75 °C

2: 66 percent / H₂ / 10 percent Pd/C / methanol / 760 Torr

3: 74 percent / NaHCO₃ / H₂O / 50 °C

4: 69 percent / PPh₃; DEAD / CHCl₃ / Heating

5: 69 percent / NaH / tetrahydrofuran / 0 °C

With diisopropoxytitanium diazide; hydrogen; sodium hydride; sodium hydrogencarbonate; triphenylphosphine; diethylazodicarboxylate; 10% palladium on active carbon; In tetrahydrofuran; methanol; chloroform; water; benzene; 1: Ring cleavage / 2: Catalytic hydrogenation / 3: Acylation / 4: Mitsunobu cyclization / 5: 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 benzyl ester (260562-76-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 66 percent / H₂ / 10 percent Pd/C / methanol / 760 Torr

2: 74 percent / NaHCO₃ / H₂O / 50 °C

3: 69 percent / PPh₃; DEAD / CHCl₃ / Heating

4: 69 percent / NaH / tetrahydrofuran / 0 °C

With hydrogen; sodium hydride; sodium hydrogencarbonate; triphenylphosphine; diethylazodicarboxylate; 10% palladium on active carbon; In tetrahydrofuran; methanol; chloroform; water; 1: Catalytic hydrogenation / 2: Acylation / 3: Mitsunobu cyclization / 4: Methylation;

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

upstream raw materials:

N-benzyloxycarbonyl-3(S)-amino-1,2(S)epoxy-4-phenylbutane

methyl iodide

(R,R)-3-(phenylmethyl)oxiranemethanol

(2S,3S)-2-azido-1-phenyl-butane-3,4-diol

Downstream raw materials:

((1S,2R)-1-Benzyl-3-cyano-2-methoxymethoxy-propyl)-methyl-carbamic acid benzyl ester

(3R,4R)-4-[(benzyloxycarbonyl)(methyl) amino]-3-(methoxymethoxy)-5-phenylpentanoic Acid

((1S,2R)-1-Benzyl-3-cyano-2-hydroxy-propyl)-methyl-carbamic acid benzyl ester