(2S,3S)-3-hydroxy-1,2-Pyrrolidinedicarboxylic acid, 1-(phenylMethyl) ester

Base Information

• Chemical Name: (2S,3S)-3-hydroxy-1,2-Pyrrolidinedicarboxylic acid, 1-(phenylMethyl) ester
• CAS No.: 174389-11-8
• Molecular Formula: C13H15NO5
• Molecular Weight: 265.266
• Mol file: 174389-11-8.mol

Synonyms:Cbz-(3S)- 3-hydroxy- D-Proline;(2R, 3S)-1-N-Cbz-3-hydroxy-pyrrolidine-2-carboxylic acid;(2R,3S)-N-(benzyloxycarbonyl)-3-hydroxypyrrolidine-2-carboxylic acid;(2R,3S)-1-[(Benzyloxy)carbonyl]-3-hydroxypyrrolidine-2-carboxylic acid;(2S,3S)-3-hydroxy-1,2-Pyrrolidinedicarboxylic acid, 1-(phenylMethyl) ester;1,2-Pyrrolidinedicarboxylic acid, 3-hydroxy-, 1-(phenylmethyl) ester, (2R,3S)-

Chemical Property of (2S,3S)-3-hydroxy-1,2-Pyrrolidinedicarboxylic acid, 1-(phenylMethyl) ester

Chemical Property:

• PSA: 87.07000
• LogP: 0.78090

Purity/Quality:

99% ^*data from raw suppliers

(2R,3S)-1-N-Cbz-3-hydroxy-pyrrolidine-2-carboxylicacid 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (2S,3S)-3-hydroxy-1,2-Pyrrolidinedicarboxylic acid, 1-(phenylMethyl) ester

There total 16 articles about (2S,3S)-3-hydroxy-1,2-Pyrrolidinedicarboxylic acid, 1-(phenylMethyl) 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: 92.0%

(2R,3S)-N-(benzyloxycarbonyl)-3-(tert-butyldiphenylsiloxy)pyrrolidine-2-carboxylic acid (174222-08-3) → (2R,3S)-N-(benzyloxycarbonyl)-3-hydroxypyrrolidine-2-carboxylic acid (174389-11-8)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; for 48h; Heating;

DOI:10.1021/jo951444u

Reference yield:

[(2S)-1-(tert-butyl-dimethyl-silanyloxymethyl)-2-oxo-ethyl]-carbamic acid benzyl ester (154161-01-0) → (2R,3S)-N-(benzyloxycarbonyl)-3-hydroxypyrrolidine-2-carboxylic acid (174389-11-8)

Guidance literature:

Multi-step reaction with 8 steps

1: 88 percent / SnCl₄ / CH₂Cl₂ / 1 h / -78 °C

2: 2,6-lutidine / CH₂Cl₂ / 18 h / 20 °C

3: 81 percent / 4-methylmorpholine N-oxide; OsO₄ / H₂O; acetone; 2-methyl-propan-2-ol / 20 °C

4: sodim periodate; silica gel / CH₂Cl₂; H₂O / 20 °C

5: NaBH₃CN; AcOH / methanol

6: 2.6 g / AcOH / methanol / 1 h / Heating

7: sodium periodate; RuCl₃*xH₂O / CCl₄; acetonitrile; H₂O / 20 °C

8: 67 mg / hydrofluoric acid; silica gel / acetonitrile / 0.83 h / 50 - 60 °C

With 2,6-dimethylpyridine; ruthenium trichloride; sodium periodate; osmium(VIII) oxide; hydrogen fluoride; silica gel; tin(IV) chloride; sodium cyanoborohydride; acetic acid; 4-methylmorpholine N-oxide; In methanol; tetrachloromethane; dichloromethane; water; acetone; acetonitrile; tert-butyl alcohol;

DOI:10.1016/S0957-4166(02)00255-0

Reference yield:

(2R,3S)-3-triisopropylsilanyloxypyrrolidine-1,2-dicarboxylic acid 1-benzyl ester (154161-03-2) → (2R,3S)-N-(benzyloxycarbonyl)-3-hydroxypyrrolidine-2-carboxylic acid (174389-11-8)

Guidance literature:

With fluorosilicic acid; In water; acetonitrile; at 55 ℃; for 0.833333h;

DOI:10.1016/S0040-4039(00)61611-8

upstream raw materials:

(2R,3S)-3-triisopropylsilanyloxypyrrolidine-1,2-dicarboxylic acid 1-benzyl ester

(2R,3S)-N-(benzyloxycarbonyl)-3-(tert-butyldiphenylsiloxy)pyrrolidine-2-carboxylic acid

[(2S)-1-(tert-butyl-dimethyl-silanyloxymethyl)-2-oxo-ethyl]-carbamic acid benzyl ester

(1S,2S)-[1-(tert-butyldimethylsilanyloxymethyl)-2-hydroxypent-4-enyl]carbamic acid benzyl ester

Downstream raw materials:

allyl (5R,6S)-2-<((2R,4R)-4-hydroxy-1-prolinamido)methyl>-6-<(R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>penem-3-carboxylate

(2R,3S)-3-Hydroxy-pyrrolidine-2-carboxylic acid methyl ester

(+)-cis-(2R,3S)-3-hydroxyproline

Refernces

• 1、 Mulzer, Johann,Meier, Andreas,Buschmann, Juergen,Luger, Peter. "Total synthesis of cis- and trans-3-hydroxy-D-proline and (+)-detoxinine". . p. 566 - 572. Retrieved 2007/10/03.