benzyl (2S,3R)-3-((benzyloxy)carbonylamino)-2-(((4-methylphenyl)sulfonyl)oxymethyl)-pyrrolidine-1-carboxylate

Base Information

• Chemical Name: benzyl (2S,3R)-3-((benzyloxy)carbonylamino)-2-(((4-methylphenyl)sulfonyl)oxymethyl)-pyrrolidine-1-carboxylate
• CAS No.: 1194059-18-1
• Molecular Formula: C₂₈H₃₀N₂O₇S
• Molecular Weight: 538.621
• Mol file: 1194059-18-1.mol

Synonyms:benzyl (2S,3R)-3-((benzyloxy)carbonylamino)-2-(((4-methylphenyl)sulfonyl)oxymethyl)-pyrrolidine-1-carboxylate

Chemical Property of benzyl (2S,3R)-3-((benzyloxy)carbonylamino)-2-(((4-methylphenyl)sulfonyl)oxymethyl)-pyrrolidine-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl (2S,3R)-3-((benzyloxy)carbonylamino)-2-(((4-methylphenyl)sulfonyl)oxymethyl)-pyrrolidine-1-carboxylate

There total 8 articles about benzyl (2S,3R)-3-((benzyloxy)carbonylamino)-2-(((4-methylphenyl)sulfonyl)oxymethyl)-pyrrolidine-1-carboxylate 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: 86.0%

benzyl (2S,3R)-3-[(benzyloxy)carbonyl]amino-2-(hydroxymethyl)pyrrolidine-1-carboxylate (1194056-93-3) + p-toluenesulfonyl chloride (98-59-9) → benzyl (2S,3R)-3-((benzyloxy)carbonylamino)-2-(((4-methylphenyl)sulfonyl)oxymethyl)-pyrrolidine-1-carboxylate (1194059-18-1)

Guidance literature:

With pyridine; at 0 - 20 ℃; for 25.5h; Inert atmosphere;

Reference yield:

(2S,3R)-methyl N-benzyloxycarbonyl-3-(benzyloxycarbonylamino)proline → benzyl (2S,3R)-3-((benzyloxy)carbonylamino)-2-(((4-methylphenyl)sulfonyl)oxymethyl)-pyrrolidine-1-carboxylate (1194059-18-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: lithium borohydride / tetrahydrofuran / 42 h / 0 - 20 °C / Inert atmosphere

1.2: Inert atmosphere

2.1: pyridine / 25.5 h / 0 - 20 °C / Inert atmosphere

With pyridine; lithium borohydride; In tetrahydrofuran;

Reference yield:

1-benzyl 2-methyl(2S,3S)-3-hydroxypyrrolidine-1,2-dicarboxylate → benzyl (2S,3R)-3-((benzyloxy)carbonylamino)-2-(((4-methylphenyl)sulfonyl)oxymethyl)-pyrrolidine-1-carboxylate (1194059-18-1)

Guidance literature:

Multi-step reaction with 6 steps

1.1: pyridine / 64 h / 0 - 20 °C / Inert atmosphere

2.1: sodium azide / N,N-dimethyl-formamide / 16 h / 50 °C / Inert atmosphere

3.1: triphenylphosphine / tetrahydrofuran / 1 h / 0 - 20 °C / Inert atmosphere

3.2: 18 h / 20 - 55 °C / Inert atmosphere

4.1: sodium hydrogencarbonate / tetrahydrofuran / 20 °C / Inert atmosphere

5.1: lithium borohydride / tetrahydrofuran / 42 h / 0 - 20 °C / Inert atmosphere

5.2: Inert atmosphere

6.1: pyridine / 25.5 h / 0 - 20 °C / Inert atmosphere

With pyridine; lithium borohydride; sodium azide; sodium hydrogencarbonate; triphenylphosphine; In tetrahydrofuran; N,N-dimethyl-formamide;

upstream raw materials:

benzyl (2S,3R)-3-[(benzyloxy)carbonyl]amino-2-(hydroxymethyl)pyrrolidine-1-carboxylate

p-toluenesulfonyl chloride

1-benzyl 2-methyl (2S,3R)-3-azido-pyrrolidine-1,2-dicarboxylate

1-benzyl 2-methyl (2S,3S)-3-((3-nitrophenyl)sulfonyloxy)pyrrolidine-1,2-dicarboxylate

Downstream raw materials:

benzyl (2R,3R)-3-((benzyloxy)carbonylamino)-2-((tert-butoxycarbonylamino)methyl)-pyrrolidine-1-carboxylate

benzyl (2R,3R)-3-((benzyloxy)carbonylamino)-2-azidomethyl-pyrrolidine-1-carboxylate