(2S,4S)-N-1-(benzyloxycarbonyl)-4-(p-toluenesulfonyloxy)proline methyl ester

Base Information

• Chemical Name: (2S,4S)-N-1-(benzyloxycarbonyl)-4-(p-toluenesulfonyloxy)proline methyl ester
• CAS No.: 77345-53-0
• Molecular Formula: C₂₁H₂₃NO₇S
• Molecular Weight: 433.482
• Mol file: 77345-53-0.mol

Synonyms:(2S,4S)-N-1-(benzyloxycarbonyl)-4-(p-toluenesulfonyloxy)proline methyl ester

Chemical Property of (2S,4S)-N-1-(benzyloxycarbonyl)-4-(p-toluenesulfonyloxy)proline methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4S)-N-1-(benzyloxycarbonyl)-4-(p-toluenesulfonyloxy)proline methyl ester

There total 5 articles about (2S,4S)-N-1-(benzyloxycarbonyl)-4-(p-toluenesulfonyloxy)proline methyl 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: 70.0%

methyl (2S,4R)-1-benzyloxycarbonyl-4-hydroxypyrrolidine-2-carboxylate (64187-48-0) + methyl p-toluene sulfonate (80-48-8) → (2S,4S)-N-1-(benzyloxycarbonyl)-4-(p-toluenesulfonyloxy)proline methyl ester (77345-53-0)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at -10 - 20 ℃; for 13h;

DOI:10.1039/b407292h

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → (2S,4S)-N-1-(benzyloxycarbonyl)-4-(p-toluenesulfonyloxy)proline methyl ester (77345-53-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 98 percent / NaHCO₃ / H₂O

2: 94 percent / SOCl₂

3: 60 percent / PPh₃; DIAD / tetrahydrofuran

With thionyl chloride; di-isopropyl azodicarboxylate; sodium hydrogencarbonate; triphenylphosphine; In tetrahydrofuran; water;

DOI:10.1039/b308581c

Reference yield:

4R-4-hydroxyproline (51-35-4,30724-02-8) → (2S,4S)-N-1-(benzyloxycarbonyl)-4-(p-toluenesulfonyloxy)proline methyl ester (77345-53-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 98 percent / NaHCO₃ / H₂O

2: 94 percent / SOCl₂

3: 60 percent / PPh₃; DIAD / tetrahydrofuran

With thionyl chloride; di-isopropyl azodicarboxylate; sodium hydrogencarbonate; triphenylphosphine; In tetrahydrofuran; water;

DOI:10.1039/b308581c

upstream raw materials:

diazomethane

(2S,4S)-1-benzyloxycarbonyl-4-hydroxyproline

methyl (2S,4R)-1-benzyloxycarbonyl-4-hydroxypyrrolidine-2-carboxylate

methyl p-toluene sulfonate

Downstream raw materials:

cis-1-benzyloxycarbonyl-4-(toluene-4-sulfonyloxy)-L-proline

trans-4-methylsulfanyl-L-proline

[1(S),4R]-1-[N-(1-carboxy-3-phenylpropyl)-L-alanyl]-4-(phenylthio)-L-proline

trans-4-(phenylthio)-L-propline