N-CBZ-TRANS-4-HYDROXY-D-PROLINE METHYL ESTER

Base Information

• Chemical Name: N-CBZ-TRANS-4-HYDROXY-D-PROLINE METHYL ESTER
• CAS No.: 79433-95-7
• Molecular Formula: C14H17NO5
• Molecular Weight: 279.293
• Mol file: 79433-95-7.mol

Synonyms:N-CBZ-TRANS-4-HYDROXY-D-PROLINE METHYL ESTER;(2R,4S)-1-benzyl 2-Methyl 4-hydroxypyrrolidine-1,2-dicarboxylate;(2R,4S)-4-Hydroxy-1,2-pyrrolidinedicarboxylic acid 2-methyl 1-(phenylmethyl) ester;N-Carbobenzoxy-trans-4-Hydroxy-D-proline methyl ester

Chemical Property of N-CBZ-TRANS-4-HYDROXY-D-PROLINE METHYL ESTER

Chemical Property:

• Boiling Point: 422.8±45.0 °C(Predicted)
• PKA: 14.25±0.40(Predicted)
• PSA: 76.07000
• Density: 1.313±0.06 g/cm3(Predicted)
• LogP: 0.86930
• Storage Temp.: 2-8°C

Purity/Quality:

95-99% ^*data from raw suppliers

N-CBZ-TRANS-4-HYDROXY-D-PROLINEMETHYLESTER 95 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of N-CBZ-TRANS-4-HYDROXY-D-PROLINE METHYL ESTER

There total 13 articles about N-CBZ-TRANS-4-HYDROXY-D-PROLINE 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: 100.0%

methanol (67-56-1) + (4S)-1-[(benzyloxy)carbonyl]-4-hydroxy-D-proline (155153-78-9) → (2R,4S)-1-benzyl 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate (79433-95-7)

Guidance literature:

With thionyl chloride; at 0 - 20 ℃; for 12h;

Reference yield: 55.0%

→ (2R,4S)-1-benzyl 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate (79433-95-7)

Guidance literature:

With sodium carbonate; In 1,4-dioxane; water; at 0 ℃; for 2.5h;

Reference yield: 23.0%

(2R,4R)-1-benzyl 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate (155075-23-3) → (2R,4S)-1-benzyl 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate (79433-95-7)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; 4-nitro-benzoic acid; In benzene; at 20 ℃; for 6h;

upstream raw materials:

trans-4-hydroxy-D,L-proline

benzyl chloroformate

diazomethane

(4S)-1-[(benzyloxy)carbonyl]-4-hydroxy-D-proline

Downstream raw materials:

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

(2R,4S)-4-(tert-butyl-dimethyl-silanyloxy)-2-hydroxymethyl-pyrrolidine-1-carboxylic acid benzyl ester

(2R,4S)-4-(tert-butyl-dimethyl-silanyloxy)-2-formyl-pyrrolidine-1-carboxylic acid benzyl ester

(2R,4S)-4-(tert-butyl-dimethyl-silanyloxy)-2-[hydroxy-(1,3,5-trimethyl-1H-pyrazol-4-yl)-methyl]-pyrrolidine-1-carboxylic acid benzyl ester

Refernces

• 1、 Ganesh, Krishna N,More, Shahaji H. "Spiegelmeric 4R/S-hydroxy/amino-L/D-prolyl collagen peptides: conformation and morphology of self-assembled structures". . . Retrieved 2020/03/11.
• 2、 -. "Dihydropyridine compound and application thereof to drugs". Paragraph 0379; 0380-0382; 0472; 0473-0475. . Retrieved 2019/05/08.