(2S,4R)-1-benzyloxycarbonyl-2-carbamoylmethyloxymethyl-4-methanesulfonyloxypyrrolidine

Base Information

• Chemical Name: (2S,4R)-1-benzyloxycarbonyl-2-carbamoylmethyloxymethyl-4-methanesulfonyloxypyrrolidine
• CAS No.: 117811-81-1
• Molecular Formula: C₁₆H₂₂N₂O₇S
• Molecular Weight: 386.426
• Mol file: 117811-81-1.mol

Synonyms:(2S,4R)-1-benzyloxycarbonyl-2-carbamoylmethyloxymethyl-4-methanesulfonyloxypyrrolidine

Chemical Property of (2S,4R)-1-benzyloxycarbonyl-2-carbamoylmethyloxymethyl-4-methanesulfonyloxypyrrolidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4R)-1-benzyloxycarbonyl-2-carbamoylmethyloxymethyl-4-methanesulfonyloxypyrrolidine

There total 8 articles about (2S,4R)-1-benzyloxycarbonyl-2-carbamoylmethyloxymethyl-4-methanesulfonyloxypyrrolidine 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:

concentrated ammonia water + (2S,4R)-1-benzyloxycarbonyl-2-(carboxymethyloxymethyl)-4-methanesulfonyloxypyrrolidine (117811-80-0) + isobutyl chloroformate (543-27-1) → (2S,4R)-1-benzyloxycarbonyl-2-carbamoylmethyloxymethyl-4-methanesulfonyloxypyrrolidine (117811-81-1)

Guidance literature:

With triethylamine; In tetrahydrofuran; methanol; chloroform;

Reference yield:

(2S,4R)-1-benzyloxycarbonyl-2-(ethoxycarbonylmethyl)oxymethyl-4-methanesulfonyloxypyrrolidine (117811-88-8) → (2S,4R)-1-benzyloxycarbonyl-2-carbamoylmethyloxymethyl-4-methanesulfonyloxypyrrolidine (117811-81-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 2N aq. NaOH / tetrahydrofuran / 20 - 25 °C

2: Et₃N / tetrahydrofuran

3: NH₃ / tetrahydrofuran / -10 °C

With sodium hydroxide; ammonia; triethylamine; In tetrahydrofuran;

DOI:10.1016/S0968-0896(97)00142-9

Reference yield:

(2S,4R)-2-(2-Isobutoxycarbonyloxy-2-oxo-ethoxymethyl)-4-methanesulfonyloxy-pyrrolidine-1-carboxylic acid benzyl ester → (2S,4R)-1-benzyloxycarbonyl-2-carbamoylmethyloxymethyl-4-methanesulfonyloxypyrrolidine (117811-81-1)

Guidance literature:

With ammonia; In tetrahydrofuran; at -10 ℃; Yield given;

DOI:10.1016/S0968-0896(97)00142-9

upstream raw materials:

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

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

(2S,4R)-1-benzyloxycarbonyl-2-hydroxymethyl-4-methanesulfonyloxypyrrolidine

(2S,4R)-1-benzyloxycarbonyl-2-(carboxymethyloxymethyl)-4-methanesulfonyloxypyrrolidine

Downstream raw materials:

(2S,4R)-2-[(2-aminoethyl)oxymethyl]-1-benzyloxycarbonyl-4-methanesulfonyloxypyrrolidine

(2S,4R)-1-benzyloxycarbonyl-4-methanesulfonyloxy-2-[(2-ureidoethyl)oxymethyl]pyrrolidine