Boc-D-Leucinol

Base Information

• Chemical Name: Boc-D-Leucinol
• CAS No.: 106930-51-2
• Molecular Formula: C11H23NO3
• Molecular Weight: 217.309
• Hs Code.: 2924199090
• European Community (EC) Number: 967-075-8
• DSSTox Substance ID: DTXSID80583402
• Nikkaji Number: J3.539.862G
• Wikidata: Q72449798
• Mol file: 106930-51-2.mol

Synonyms:Boc-D-Leucinol;106930-51-2;N-BOC-D-Leucinol;(R)-tert-Butyl (1-hydroxy-4-methylpentan-2-yl)carbamate;TERT-BUTYL N-[(2R)-1-HYDROXY-4-METHYLPENTAN-2-YL]CARBAMATE;Boc-D-Leu-ol;tert-butyl (R)-(1-hydroxy-4-methylpentan-2-yl)carbamate;(R)-N-(tert-Butoxycarbonyl)leucinol;Boc-D-Leucinol, 97%;SCHEMBL4032796;DTXSID80583402;LQTMEOSBXTVYRM-SECBINFHSA-N;MFCD00235931;N-alpha-t-Butyloxycarbonyl-D-leucinol;AKOS015900090;AC-24085;AS-19002;2(R)-t-Butoxycarbonylamino-4-methylpentanol;CS-0101224;EN300-6193654;A801536;J-007600;J-640378;J-800384;Q-101628;(R)-tert-butyl 1-hydroxy-4-methylpentan-2-ylcarbamate;tert-Butyl [(2R)-1-hydroxy-4-methylpentan-2-yl]carbamate;tert-butyl N-[(2R)-4-methyl-1-oxidanyl-pentan-2-yl]carbamate;((R)-1-hydroxymethyl-3-methyl-butyl)-carbamic acid tert-butyl ester;N-[(2R)-1-hydroxy-4-methylpentan-2-yl]carbamic acid tert-butyl ester

Chemical Property of Boc-D-Leucinol

Chemical Property:

• Vapor Pressure: 2.8E-05mmHg at 25°C
• Refractive Index: n20/D 1.449(lit.)
• Boiling Point: 319.3 °C at 760 mmHg
• PKA: 12.11±0.46(Predicted)
• Flash Point: 146.9 °C
• PSA: 58.56000
• Density: 0.984 g/cm³
• LogP: 2.30900
• Storage Temp.: Store at 0°C
• XLogP3: 2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 217.16779360
• Heavy Atom Count: 15
• Complexity: 197

Purity/Quality:

98% ^*data from raw suppliers

Boc-D-Leucinol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CC(CO)NC(=O)OC(C)(C)C
• Isomeric SMILES: CC(C)C[C@H](CO)NC(=O)OC(C)(C)C

Technology Process of Boc-D-Leucinol

There total 12 articles about Boc-D-Leucinol 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: 72.0%

di-tert-butyl dicarbonate (24424-99-5) + C22H28N2O5 → tert-butyl [(2R)-1-hydroxy-4-methylpentan-2-yl]carbamate (106930-51-2)

Guidance literature:

With palladium dichloride; In methanol; water; at 25 ℃; for 10h; Green chemistry;

DOI:10.1016/j.tetlet.2015.12.116

Reference yield: 53.0%

N-Boc-D-Leu (16937-99-8,53296-34-7) → tert-butyl [(2R)-1-hydroxy-4-methylpentan-2-yl]carbamate (106930-51-2)

Guidance literature:

N-Boc-D-Leu; With 4-methyl-morpholine; isobutyl chloroformate; In tetrahydrofuran; at -20 ℃; for 0.5h; Inert atmosphere;

With sodium tetrahydroborate; In water; at 0 ℃;

DOI:10.1002/anie.202008992

Reference yield:

2-amino-4-methyl-1-pentanol (7533-40-6,16369-17-8,53448-09-2,502-32-9,14438-11-0) + di-tert-butyl dicarbonate (24424-99-5) → tert-butyl [(2R)-1-hydroxy-4-methylpentan-2-yl]carbamate (106930-51-2)

Guidance literature:

With triethylamine; In tetrahydrofuran; 1,4-dioxane;

upstream raw materials:

N-Boc-D-Leu

methyl (2R)-2-(tert-butoxycarbonylamino)-4-methylpentanoate

di-tert-butyl dicarbonate

N-tert-butyloxycarbonyl-L-serine methyl ester

Downstream raw materials:

((R)-1-aminomethyl-3-methyl-butyl)-carbamic acid tert-butyl ester

tert-butyl [(3R)-1-hydroxy-5-methylhexan-3-yl]carbamate

[3-methyl-1-[[[(4-methylphenyl)sulfonyl]oxy]methyl]butyl]-1,1-dimethylethyl carbamic ester

(R)-3-(N-tert-butoxycarbonyl-2-amino-4-methylpentyl)-1-(2,6-difluorobenzyl)-5-(2-fluoro-3-methoxyphenyl)-6-methyluracil

Refernces

• 1、 Cussol, Léonie,Mauran-Ambrosino, Laura,Buratto, Jérémie,Belorusova, Anna Y,Neuville, Maxime,Osz, Judit,Fribourg, Sébastien,Fremaux, Juliette,Dolain, Christel,Goudreau, Sébastien R.,Rochel, Natacha,Guichard, Gilles. "Structural Basis for α-Helix Mimicry and Inhibition of Protein–Protein Interactions with Oligourea Foldamers". supporting information. p. 2296 - 2303. Retrieved 2020/12/07.
• 2、 Reddy Guduru, Shiva Krishna,Chamakuri, Srinivas,Raji, Idris O.,MacKenzie, Kevin R.,Santini, Conrad,Young, Damian W.. "Synthesis of Enantiomerically Pure 3-Substituted Piperazine-2-acetic Acid Esters as Intermediates for Library Production". . p. 11777 - 11793. Retrieved 2018/09/27.