BOC-D-LEUCINE METHYL ESTER

Base Information

• Chemical Name: BOC-D-LEUCINE METHYL ESTER
• CAS No.: 133467-01-3
• Molecular Formula: C12H23NO4
• Molecular Weight: 245.319
• Mol file: 133467-01-3.mol

Synonyms:N-TERT-BUTOXYCARBONYL-D-LEUCINE METHYL ESTER;METHYL BOC-D-LEUCINATE;

Chemical Property of BOC-D-LEUCINE METHYL ESTER

Chemical Property:

• Boiling Point: 322.5±25.0 °C(Predicted)
• PKA: 11.21±0.46(Predicted)
• PSA: 64.63000
• Density: 1.008±0.06 g/cm3(Predicted)
• LogP: 2.48970
• Storage Temp.: 2-8°C

Purity/Quality:

98% ^*data from raw suppliers

Boc-D-Leu-OMe ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of BOC-D-LEUCINE METHYL ESTER

There total 13 articles about BOC-D-LEUCINE 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: 99.0%

di-tert-butyl dicarbonate (24424-99-5) + (R)-leucine methyl ester hydrochloride (5845-53-4,6322-53-8,7517-19-3) → methyl (2R)-2-(tert-butoxycarbonylamino)-4-methylpentanoate (133467-01-3)

Guidance literature:

With sodium hydrogencarbonate; In 1,4-dioxane; water; at 20 ℃; for 20h; Inert atmosphere;

DOI:10.1002/anie.201603288

Reference yield: 92.0%

D-leucine methyl ester (23032-21-5) + di-tert-butyl dicarbonate (24424-99-5) → methyl (2R)-2-(tert-butoxycarbonylamino)-4-methylpentanoate (133467-01-3)

Guidance literature:

With sodium hydrogencarbonate; In 1,4-dioxane; water;

DOI:10.1021/jm3012273

Reference yield:

methyl 2-((tert-butoxycarbonyl)amino)-4-methylpentanoate (69805-63-6) → N-tert-butoxycarbonyl-L-leucine (13139-15-6,53296-34-7) + N-Boc-D-Leu (16937-99-8,53296-34-7) + N-tert-butoxycarbonyl-L-leucine methyl ester (63096-02-6) + methyl (2R)-2-(tert-butoxycarbonylamino)-4-methylpentanoate (133467-01-3)

Guidance literature:

With Bacillus licheniformis; In water; pH=7.8; Heating;

DOI:10.1016/j.tetasy.2006.07.012

upstream raw materials:

diazomethane

N-Boc-D-Leu

methyl iodide

di-tert-butyl dicarbonate

Downstream raw materials:

tert-butyl [(2R)-1-hydroxy-4-methylpentan-2-yl]carbamate

3-({1-[1-(9H-fluoren-9-ylmethoxycarbonylamino)-3-methyl-butyl]-but-3-enyloxy}-dimethylsilanyloxy)-2-isobutyl-pent-4-enethioic acid S-benzyl ester

3-({1-[1-(9H-fluoren-9-ylmethoxycarbonylamino)-3-methyl-butyl]-but-3-enyloxy}-dimethylsilanyloxy)-2-isobutyl-pent-4-enethioic acid S-benzyl ester

3-({1-[1-(9H-fluoren-9-ylmethoxycarbonylamino)-3-methyl-butyl]-but-3-enyloxy}-dimethylsilanyloxy)-2-isobutyl-pent-4-enethioic acid S-benzyl ester

Refernces

• 1、 Steinmetz, Heinrich,Li, Jun,Fu, Chengzhang,Zaburannyi, Nestor,Kunze, Birgitte,Harmrolfs, Kirsten,Schmitt, Viktoria,Herrmann, Jennifer,Reichenbach, Hans,H?fle, Gerhard,Kalesse, Markus,Müller, Rolf. "Isolation, Structure Elucidation, and (Bio)Synthesis of Haprolid, a Cell-Type-Specific Myxobacterial Cytotoxin". supporting information. p. 10113 - 10117. Retrieved 2016/08/16.
• 2、 Karlstr?m, Sofia,Nordvall, Gunnar,Sohn, Daniel,Hettman, Andreas,Turek, Dominika,?hlin, Kristofer,Kers, Annika,Claesson, Martina,Slivo, Can,Lo-Alfredsson, Yvonne,Petersson, Carl,Bessidskaia, Galina,Svensson, Per H.,Rein, Tobias,Jerning, Eva,Malmberg, ?sa,Ahlgen, Charlotte,Ray, Colin,Vares, Lauri,Ivanov, Vladimir,Johansson, Rolf. "Substituted 7-amino-5-thio-thiazolo[4,5- d ]pyrimidines as potent and selective antagonists of the fractalkine receptor (CX3CR1)". supporting information. p. 3177 - 3190. Retrieved 2013/06/05.