Z-CIS-HYP-OH

Base Information

• Chemical Name: Z-CIS-HYP-OH
• CAS No.: 13504-86-4
• Molecular Formula: C13H15NO5
• Molecular Weight: 265.266
• Mol file: 13504-86-4.mol

Synonyms:1,2-Pyrrolidinedicarboxylicacid, 4-hydroxy-, 1-(phenylmethyl) ester, (2S-cis)-;1,2-Pyrrolidinedicarboxylicacid, 4-hydroxy-, 1-benzyl ester, L-cis- (8CI);(2S,4S)-1-(Benzyloxycarbonyl)-2-(carboxy)-4-hydroxypyrrolidine;N-(Benzyloxycarbonyl)-cis-4-Hydroxy-D-proline;N-(Benzyloxycarbonyl)-cis-4-hydroxy-L-proline;

Chemical Property of Z-CIS-HYP-OH

Chemical Property:

• Vapor Pressure: 2.71E-10mmHg at 25°C
• Refractive Index: 1.612
• Boiling Point: 486.876 °C at 760 mmHg
• PKA: 3.78±0.40(Predicted)
• Flash Point: 248.254 °C
• PSA: 87.07000
• Density: 1.416 g/cm³
• LogP: 0.78090
• Storage Temp.: 2-8°C

Purity/Quality:

98%,99%, ^*data from raw suppliers

Z-L-cis-4-hydroxyproline 99+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Z-CIS-HYP-OH

There total 22 articles about Z-CIS-HYP-OH 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%

(2S,4S)-N-benzyloxycarbonyl-4-formyloxyproline methyl ester (170159-62-3) → (2S,4S)-1-benzyloxycarbonyl-4-hydroxyproline (13504-86-4)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; at 25 ℃; for 0.5h;

Reference yield: 90.2%

methyl (2S,4R)-1-benzyloxycarbonyl-4-methanesulfonyloxypyrrolidine-2-carboxylate (117811-78-6) → (2S,4S)-1-benzyloxycarbonyl-4-hydroxyproline (13504-86-4)

Guidance literature:

With water; sodium hydroxide; at 80 ℃; for 3h;

Reference yield: 84.0%

benzyl chloroformate (501-53-1,94274-21-2) + hydroxy L-proline (618-27-9,30724-02-8) → (2S,4S)-1-benzyloxycarbonyl-4-hydroxyproline (13504-86-4)

Guidance literature:

With sodium hydrogencarbonate; In tetrahydrofuran; at 20 ℃;

DOI:10.1111/cbdd.13743

upstream raw materials:

benzyl chloroformate

hydroxy L-proline

1-benzyloxycarbonyl-4-keto-L-proline

(2S,4S)-N-benzyloxycarbonyl-4-formyloxyproline methyl ester

Downstream raw materials:

(4S)-1-benzyloxycarbonyl-N-t-butyl-4-hydroxy-L-prolinamide

(2S,4S)-4-hydroxypyrrolidine-1,2-dicarboxylic acid 1-benzyl 2-methyl

N-<(phenylmethoxy)carbonyl>-4(S)-methoxy-(S)-proline methyl ester

N-(benzyloxycarbonyl)-cis-4'-(benzyloxy)-L-proline

Refernces

• 1、 -. "DIMERIC PEPTIDE INHIBITORS OF APOPTOSIS PROTEINS". Paragraph 0156. . Retrieved 2019/02/13.
• 2、 Mereyala, Hari Babu,Pathuri, Gopal,Nagarapu, Lingaiah. "Synthesis of (2S,4S)-4-hydroxyproline from D-glucose". . p. 1278 - 1287. Retrieved 2012/04/17.