cis-1-(Benzyloxycarbonyl)-4-hydroxy-D-proline tert-butyl ester

Base Information

• Chemical Name: cis-1-(Benzyloxycarbonyl)-4-hydroxy-D-proline tert-butyl ester
• CAS No.: 159487-60-2
• Molecular Formula: C₁₇H₂₃NO₅
• Molecular Weight: 321.373
• Mol file: 159487-60-2.mol

Synonyms:cis-1-(Benzyloxycarbonyl)-4-hydroxy-D-proline tert-butyl ester

Chemical Property of cis-1-(Benzyloxycarbonyl)-4-hydroxy-D-proline tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of cis-1-(Benzyloxycarbonyl)-4-hydroxy-D-proline tert-butyl ester

There total 3 articles about cis-1-(Benzyloxycarbonyl)-4-hydroxy-D-proline tert-butyl 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:

(2R,4R)-4-hydroxypyrrolidine-2-carboxylic acid hydrochloride (77449-94-6,441067-49-8) → cis-1-(Benzyloxycarbonyl)-4-hydroxy-D-proline tert-butyl ester (159487-60-2)

Guidance literature:

Multi-step reaction with 2 steps

1: NaHCO₃ / H₂O / 2 h

2: tetrahydrofuran / 1.) r.t., 30 min, 2.) 55 deg C, 20.5 h

With sodium hydrogencarbonate; In tetrahydrofuran; water;

DOI:10.1021/jo00092a022

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → cis-1-(Benzyloxycarbonyl)-4-hydroxy-D-proline tert-butyl ester (159487-60-2)

Guidance literature:

Multi-step reaction with 2 steps

1: NaHCO₃ / H₂O / 2 h

2: tetrahydrofuran / 1.) r.t., 30 min, 2.) 55 deg C, 20.5 h

With sodium hydrogencarbonate; In tetrahydrofuran; water;

DOI:10.1021/jo00092a022

Reference yield:

4R-4-hydroxyproline (51-35-4,30724-02-8) → cis-1-(Benzyloxycarbonyl)-4-hydroxy-D-proline tert-butyl ester (159487-60-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) AcOH, Ac₂O, 2.) 2N HCl / 1.) reflux, 5.5 h, 2.) reflux, 2 h

2: NaHCO₃ / H₂O / 2 h

3: tetrahydrofuran / 1.) r.t., 30 min, 2.) 55 deg C, 20.5 h

With hydrogenchloride; acetic anhydride; sodium hydrogencarbonate; acetic acid; In tetrahydrofuran; water;

DOI:10.1021/jo00092a022

upstream raw materials:

(2R,4R)-4-hydroxypyrrolidine-2-carboxylic acid hydrochloride

benzyl chloroformate

4R-4-hydroxyproline

Downstream raw materials:

(2R,4S)-4-Trifluoromethanesulfonyloxy-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester

(2R,4S)-1-(Benzyloxycarbonyl)-4-hydroxyproline tert-butyl ester

trans-4-Acetoxy-1-(benzyloxycarbonyl)-D-proline tert-butyl ester