Boc-L-beta-homoleucine

Base Information

• Chemical Name: Boc-L-beta-homoleucine
• CAS No.: 132549-43-0
• Molecular Formula: C₁₂H₂₃NO₄
• Molecular Weight: 245.319
• Hs Code.: 29241990
• European Community (EC) Number: 821-664-5
• DSSTox Substance ID: DTXSID30375814
• Nikkaji Number: J970.475B
• Wikidata: Q72510211
• Mol file: 132549-43-0.mol

Synonyms:132549-43-0;Boc-L-beta-homoleucine;(S)-3-((tert-Butoxycarbonyl)amino)-5-methylhexanoic acid;(3S)-5-methyl-3-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoic acid;N-Boc-L-beta-homoleucine;Hexanoic acid, 3-[[(1,1-dimethylethoxy)carbonyl]amino]-5-methyl-, (3S)-;(S)-3-(tert-butoxycarbonylamino)-5-methylhexanoic acid;Boc-beta-Homoleu-OH;Boc-L-beta-HLeu-OH;(3S)-3-{[(tert-butoxy)carbonyl]amino}-5-methylhexanoic acid;MFCD02101665;(S)-3-(Boc-amino)-5-methyl-hexanoic acid;Boc-Leu-(C#CH2)OH;SCHEMBL4934738;(3s)-n-3-t-butoxycarbonyl-3-amino-5-methyl-hexanoic acid;DTXSID30375814;XRVAMBSTOWHUMM-VIFPVBQESA-N;BCP11551;AKOS015900923;AC-22078;DS-16843;Boc-beta-Homoleu-OH, >=98.0% (TLC);CS-0012624;EN300-749581;A806457;J-640382;(3S)-3-(tert-Butoxycarbonylamino)-5-methylhexanoic acid;(S)-3-((tert-Butoxycarbonyl)amino)-5-methylhexanoicacid;S-132549-43-0;Hexanoic acid,3-[[(1,1-dimethylethoxy)carbonyl]amino]-5-methyl-,(3S)-

Chemical Property of Boc-L-beta-homoleucine

Chemical Property:

• Vapor Pressure: 1.24E-06mmHg at 25°C
• Melting Point: 53-55℃
• Refractive Index: 1.462
• Boiling Point: 374.269 °C at 760 mmHg
• PKA: 4.45±0.10(Predicted)
• Flash Point: 180.152 °C
• PSA: 75.63000
• Density: 1.047 g/cm³
• LogP: 2.79140
• Storage Temp.: 2-8°C
• Solubility.: Very slightly soluble (1.1 g/L at 25°C).
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 245.16270821
• Heavy Atom Count: 17
• Complexity: 268

Purity/Quality:

99% ^*data from raw suppliers

Boc-β-Homoleu-OH ≥98.0% (TLC) ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CC(CC(=O)O)NC(=O)OC(C)(C)C
• Isomeric SMILES: CC(C)C[C@@H](CC(=O)O)NC(=O)OC(C)(C)C
• Uses: (S)-3-(Boc-amino)-5-methylhexanoic acid is used as building blocks for the synthesis of "carba peptides" and building block for β-peptides.

Technology Process of Boc-L-beta-homoleucine

There total 27 articles about Boc-L-beta-homoleucine 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: 96.0%

Boc-(S)-β3-HLeu-OMe (86834-94-8) → N-Boc-L-β-homoleucine (138165-75-0,146398-18-7,132549-43-0)

Guidance literature:

With water; lithium hydroxide; In methanol; at 20 ℃; for 18h;

DOI:10.1002/chem.201200313

Reference yield: 92.0%

(4-hydroxy-1-isobutyl-4-methyl-3-oxopentyl)carbamic acid tert-butyl ester (748793-66-0) → N-Boc-L-β-homoleucine (138165-75-0,146398-18-7,132549-43-0)

Guidance literature:

With sodium periodate; In methanol; at 20 ℃;

DOI:10.1021/ja047004e

Reference yield: 68.0%

[(1S,3R,4R)-3,4-dihydroxy-1-isobutyl-pentyl]-carbamic acid tert-butyl ester (557091-72-2) → N-Boc-L-β-homoleucine (138165-75-0,146398-18-7,132549-43-0)

Guidance literature:

With ruthenium trichloride; sodium periodate; In tetrachloromethane; acetonitrile; at 20 ℃;

DOI:10.1021/ja0298747

upstream raw materials:

N-tert-butoxycarbonyl-L-leucine

(S)-3-amino-5-methylhexanoic acid

di-tert-butyl dicarbonate

diazomethane

Downstream raw materials:

methyl (3S)-3-amino-5-methylhexanoate

C₁₈H₃₄N₂O₃

(E)-(S)-2-Benzyl-5-tert-butoxycarbonylamino-7-methyl-oct-2-enoic acid ethyl ester

Refernces

• 1、 Fuller, Amelia A.,Chen, Bin,Minter, Aaron R.,Mapp, Anna K.. "Succinct synthesis of β-amino acids via chiral isoxazolines". . p. 5376 - 5383. Retrieved 2005.
• 2、 Peddie, Victoria,Butcher, Raymond J.,Robinson, Ward T.,Wilce, Matthew C. J.,Traore, Daouda A. K.,Abell, Andrew D.. "Synthesis and conformation of fluorinated β-peptidic compounds". . p. 6655 - 6662. Retrieved 2012/07/28.