(2S,3R,5R)-5-Hydroxy-pyrrolidine-1,2,3-tricarboxylic acid 1-benzyl ester 2-tert-butyl ester 3-methyl ester

Base Information

• Chemical Name: (2S,3R,5R)-5-Hydroxy-pyrrolidine-1,2,3-tricarboxylic acid 1-benzyl ester 2-tert-butyl ester 3-methyl ester
• CAS No.: 177472-11-6
• Molecular Formula: C₁₉H₂₅NO₇
• Molecular Weight: 379.41
• Mol file: 177472-11-6.mol

Synonyms:(2S,3R,5R)-5-Hydroxy-pyrrolidine-1,2,3-tricarboxylic acid 1-benzyl ester 2-tert-butyl ester 3-methyl ester

Chemical Property of (2S,3R,5R)-5-Hydroxy-pyrrolidine-1,2,3-tricarboxylic acid 1-benzyl ester 2-tert-butyl ester 3-methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,5R)-5-Hydroxy-pyrrolidine-1,2,3-tricarboxylic acid 1-benzyl ester 2-tert-butyl ester 3-methyl ester

There total 2 articles about (2S,3R,5R)-5-Hydroxy-pyrrolidine-1,2,3-tricarboxylic acid 1-benzyl ester 2-tert-butyl ester 3-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: 6.0%

tert-butyl (2S,3R)-2-(benzyloxycarbonylamino)-3-carbomethoxyhex-5-enoate (123975-54-2) → (2S,3R,5R)-5-Hydroxy-pyrrolidine-1,2,3-tricarboxylic acid 1-benzyl ester 2-tert-butyl ester 3-methyl ester (177472-11-6) + (2S,3R)-2-Benzyloxycarbonylamino-3-(2-oxo-ethyl)-succinic acid 1-tert-butyl ester 4-methyl ester (177288-56-1)

Guidance literature:

With sodium periodate; osmium(VIII) oxide; In methanol; water; isopropyl alcohol; for 1.25h; Ambient temperature;

DOI:10.1021/jm9601009

Reference yield:

β-Methyl α-tert-butyl (2S)-N-(benzyloxycarbonyl)aspartate (60079-12-1) → (2S,3R,5R)-5-Hydroxy-pyrrolidine-1,2,3-tricarboxylic acid 1-benzyl ester 2-tert-butyl ester 3-methyl ester (177472-11-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) lithium hexamethyldisilazide / 1.) THF, hexane, -35 deg C, 150 min, 2.) THF, hexane, -75 deg C, 18 h

2: 83 percent / OsO₄, NaIO₄ / methanol; H₂O; propan-2-ol / 1.25 h / Ambient temperature

With sodium periodate; osmium(VIII) oxide; lithium hexamethyldisilazane; In methanol; water; isopropyl alcohol;

DOI:10.1021/jm9601009

Reference yield: 74.0%

(2S,3R,5R)-5-Hydroxy-pyrrolidine-1,2,3-tricarboxylic acid 1-benzyl ester 2-tert-butyl ester 3-methyl ester (177472-11-6) → (2S,3R)-Pyrrolidine-1,2,3-tricarboxylic acid 1-benzyl ester 2-tert-butyl ester 3-methyl ester (177288-57-2)

Guidance literature:

With triethylsilane; trifluoroacetic acid; In chloroform; for 0.666667h; Ambient temperature;

DOI:10.1021/jm9601009

upstream raw materials:

tert-butyl (2S,3R)-2-(benzyloxycarbonylamino)-3-carbomethoxyhex-5-enoate

β-Methyl α-tert-butyl (2S)-N-(benzyloxycarbonyl)aspartate

Downstream raw materials:

(2S,3R)-Pyrrolidine-1,2,3-tricarboxylic acid 1-benzyl ester 2-tert-butyl ester 3-methyl ester

(2S,3R)-Pyrrolidine-1,2,3-tricarboxylic acid 1-benzyl ester 3-methyl ester

(2S,3S)-Pyrrolidine-1,2,3-tricarboxylic acid 1-benzyl ester