FMoc-(R)-3-aMino-2-(tert-butoxyMethyl)propanoic acid

Base Information

• Chemical Name: FMoc-(R)-3-aMino-2-(tert-butoxyMethyl)propanoic acid
• CAS No.: 847153-42-8
• Molecular Formula: C₂₃H₂₇NO₅
• Molecular Weight: 397.471
• Hs Code.: 2924299090
• Mol file: 847153-42-8.mol

Synonyms:FMoc-(R)-3-aMino-2-(tert-butoxyMethyl)propanoic acid

Chemical Property of FMoc-(R)-3-aMino-2-(tert-butoxyMethyl)propanoic acid

Chemical Property:

• PSA: 88.35000
• LogP: 4.24540
• Storage Temp.: 2-8°C

Purity/Quality:

98.5% ^*data from raw suppliers

(R)-3-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-2-(tert-butoxymethyl)propanoicacid 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of FMoc-(R)-3-aMino-2-(tert-butoxyMethyl)propanoic acid

There total 14 articles about FMoc-(R)-3-aMino-2-(tert-butoxyMethyl)propanoic acid 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: 90.0%

(9H-fluoren-9-yl)methyl (R)-[3-(tert-butoxy)-2-(hydroxymethyl)propyl]carbamate → (S)-2-tert-butoxymethyl-3-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid (847153-42-8)

Guidance literature:

With sodium hypochlorite; sodium chlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; In aq. phosphate buffer; water; acetonitrile; at 35 ℃; for 6h; pH=6.7; enantioselective reaction;

DOI:10.1002/ejoc.201500636

Reference yield: 88.0%

(9H-fluoren-9-yl)methyl (S)-[3-(tert-butoxy)-2-(hydroxymethyl)propyl]carbamate → (2R)-3-(1,1-dimethylethoxy)-2-[({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)methyl]propanoic acid (847153-42-8)

Guidance literature:

With sodium hypochlorite; sodium chlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; In aq. phosphate buffer; water; acetonitrile; at 35 ℃; for 6h; pH=6.7; enantioselective reaction;

DOI:10.1002/ejoc.201500636

Reference yield: 84.0%

(αR)-α-[(1,1-dimethylethoxy)methyl]-1,3-dihydro-1,3-dioxo-2H-isoindole-2-propanoic acid (1269761-20-7) + N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) → (2R)-3-(1,1-dimethylethoxy)-2-[({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)methyl]propanoic acid (847153-42-8)

Guidance literature:

(αR)-α-[(1,1-dimethylethoxy)methyl]-1,3-dihydro-1,3-dioxo-2H-isoindole-2-propanoic acid; With hydrazine; In ethanol; for 0.5h; Reflux;

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide; With sodium hydrogencarbonate; In tetrahydrofuran; water; at 0 - 20 ℃;

DOI:10.1002/hlca.201000409

upstream raw materials:

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

benzyl (R)-2-(aminomethyl)-3-(tert-butoxy)propanoate

2-({[(2R)-2-carboxy-3-(1,1-dimethylethoxy)propyl]amino}carbonyl)benzoic acid

(αR)-α-[(1,1-dimethylethoxy)methyl]-1,3-dihydro-1,3-dioxo-2H-isoindole-2-propanoic acid

Downstream raw materials:

prop-2-en-1-yl (2R)-3-(1,1-dimethylethoxy)-2-[({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)methyl]propanoate

prop-2-en-1-yl (2R)-3-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-2-(hydroxymethyl)propanoate

Refernces

• 1、 Patora-Komisarska, Krystyna,Jadwiga Podwysocka, Dominika,Seebach, Dieter. "Preparation of the β2-homoselenocysteine derivatives Fmoc-(S)-β2hSec(PMB)-OH and Boc-(S)-β2hSec(PMB)- OH for solution and solid-phase peptide synthesis". . p. 1 - 17. Retrieved 2011/03/17.
• 2、 Lelais, Gerald,Micuch, Peter,Josien-Lefebvre, Delphine,Rossi, Francesco,Seebach, Dieter. "Preparation of protected β2- and β3- homocysteine, β2- and β3-homohistidine, and β2-homoserine for solid-phase syntheses". . p. 3131 - 3159. Retrieved 2007/10/03.