BENZYL (2S)-2-CARBOBENZYLOXYAMINO-6-HYDROXYHEXANOATE

Base Information

• Chemical Name: BENZYL (2S)-2-CARBOBENZYLOXYAMINO-6-HYDROXYHEXANOATE
• CAS No.: 84246-49-1
• Molecular Formula: C21H25NO5
• Molecular Weight: 371.433
• Mol file: 84246-49-1.mol

Synonyms:6-Hydroxy-N-[(phenylmethoxy)carbonyl]-L-norleucine Phenylmethyl Ester;Benzyl (2S)-2-carbobenzyloxyamino-6-hydroxyhexanoate;(S)-benzyl 6-hydroxy-2-benzyloxycarbonylaminohexanoate;2(S)-2-(benzyloxycarbonylamino)-6-hydroxyhexanoic acid,benzyl ester;benzyl (S)-2-(benzyloxycarbonylamino)-6-hydroxyhexanoate;2(S)-2-(benzyloxycarbonylamino)-6-hydroxycaproic acid benzyl ester;

Chemical Property of BENZYL (2S)-2-CARBOBENZYLOXYAMINO-6-HYDROXYHEXANOATE

Chemical Property:

• PSA: 88.35000
• LogP: 3.39180
• Storage Temp.: Refrigerator
• Solubility.: Chloroform, Dichloromethane

Purity/Quality:

97% ^*data from raw suppliers

Benzyl(2S)-2-carbobenzyloxyamino-6-hydroxyhexanoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of BENZYL (2S)-2-CARBOBENZYLOXYAMINO-6-HYDROXYHEXANOATE

There total 15 articles about BENZYL (2S)-2-CARBOBENZYLOXYAMINO-6-HYDROXYHEXANOATE 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: 83.0%

N-benzyloxycarbonyl-α-benzylester-δ-L-α-aminoadipic acid (24325-17-5) → 2(S)-2-(benzyloxycarbonylamino)-6-hydroxyhexanoic acid, benzyl ester (84246-49-1)

Guidance literature:

With borane-THF;

DOI:10.1016/S0040-4020(01)96782-1

Reference yield: 68.3%

benzyl (S)-2-(benzyloxycarbonylamino)-5-hexenoate → 2(S)-2-(benzyloxycarbonylamino)-6-hydroxyhexanoic acid, benzyl ester (84246-49-1)

Guidance literature:

benzyl (S)-2-(benzyloxycarbonylamino)-5-hexenoate; With dimethylsulfide borane complex; In tetrahydrofuran; at 0 ℃; for 12h;

With dihydrogen peroxide; sodium acetate; In tetrahydrofuran; pH=7.5;

DOI:10.1055/s-2005-918447

Reference yield: 31.0%

formic acid (64-18-6) + C27H30N4O4 (84246-48-0) → 2(S)-2-(benzyloxycarbonylamino)-6-hydroxyhexanoic acid, benzyl ester (84246-49-1) + (S)-2-Benzyloxycarbonylamino-6-formyloxy-hexanoic acid benzyl ester (84246-50-4)

Guidance literature:

Ambient temperature;

DOI:10.1039/c39820000818

upstream raw materials:

formic acid

C₂₇H₃₀N₄O₄

N-benzyloxycarbonyl-α-benzylester-δ-L-α-aminoadipic acid

(S)-2-Benzyloxycarbonylamino-6-formyloxy-hexanoic acid benzyl ester

Downstream raw materials:

N-benzyloxycarbonyl-α-benzylester-δ-L-α-aminoadipic acid

(S)-benzyl 6-oxo-2-benzyloxycarbonylaminohexanoate

(S)-3,4-Dihydro-2H-pyridine-1,2-dicarboxylic acid dibenzyl ester

8-benzyl 1-ethyl (7S)-7-{[(benzyloxy)carbonyl]amino}-2-{[(tert-butoxy)carbonyl]amino}-2-cyanooctanedioate

Refernces

• 1、 Schmitt, Martin L.,Hauser, Alexander-Thomas,Carlino, Luca,Pippel, Martin,Schulz-Fincke, Johannes,Metzger, Eric,Willmann, Dominica,Yiu, Teresa,Barton, Michelle,Schüle, Roland,Sippl, Wolfgang,Jung, Manfred. "Nonpeptidic propargylamines as inhibitors of lysine specific demethylase 1 (LSD1) with cellular activity". . p. 7334 - 7342. Retrieved 2013/10/21.
• 2、 Shimasaki, Yasuharu,Kiyota, Hiromasa,Sato, Minoru,Kuwahara, Shigefumi. "Facile synthesis of (S)-gizzerosine - A potent inducer of gizzard erosion in chicks - Using successive zinc-mediated and palladium-catalyzed coupling reactions". . p. 3191 - 3192. Retrieved 2007/10/03.