(2S,3S)-2-(((Benzyloxy)carbonyl)(methyl)amino)-3-methylpentanoic acid

Base Information

• Chemical Name: (2S,3S)-2-(((Benzyloxy)carbonyl)(methyl)amino)-3-methylpentanoic acid
• CAS No.: 42417-66-3
• Molecular Formula: C15H21 N O4
• Molecular Weight: 279.336
• Hs Code.: 2922509090
• DSSTox Substance ID: DTXSID80427130
• Nikkaji Number: J2.344.533F
• Wikidata: Q72516280
• Mol file: 42417-66-3.mol

Synonyms:42417-66-3;Z-N-Me-Ile-OH;(2S,3S)-2-(((BENZYLOXY)CARBONYL)(METHYL)AMINO)-3-METHYLPENTANOIC ACID;N-Cbz-N-methyl-L-isoleucine;N-((benzyloxy)carbonyl)-N-methyl-L-isoleucine;Benzyloxycarbonyl-N-alpha-methyl-L-isoleucine;N-[(Benzyloxy)carbonyl]-N-methyl-L-isoleucine;(2S,3S)-3-methyl-2-[methyl(phenylmethoxycarbonyl)amino]pentanoic acid;(2S,3S)-2-{[(benzyloxy)carbonyl](methyl)amino}-3-methylpentanoic acid;SCHEMBL14957363;DTXSID80427130;QUMDFJSXQJTNDA-AAEUAGOBSA-N;AMY22569;MFCD00235876;AKOS015913767;Benzyloxycarbonyl-N-methyl-L-isoleucine;DS-2297;HY-W035914;AC-31989;CS-0088348;EN300-6746984;(2S,3S)-2-[Methyl(benzyloxycarbonyl)amino]-3-methylpentanoic acid;(2S,3S)-2-(((Benzyloxy)carbonyl)(methyl)-amino)-3-methylpentanoic acid;(2S,3S)-2-((benzyloxycarbonyl)(methyl)amino)-3-methylpentanoic acid;(2S,3S)-2-(((BENZYLOXY)CARBONYL)(METHYL)AMINO)-3-METHYLPENTANOICACID

Chemical Property of (2S,3S)-2-(((Benzyloxy)carbonyl)(methyl)amino)-3-methylpentanoic acid

Chemical Property:

• PSA: 66.84000
• LogP: 2.75430
• Storage Temp.: Store at RT.
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 279.14705815
• Heavy Atom Count: 20
• Complexity: 326

Purity/Quality:

98%,99%, ^*data from raw suppliers

Z-N-Me-ile-oh ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCC(C)C(C(=O)O)N(C)C(=O)OCC1=CC=CC=C1
• Isomeric SMILES: CC[C@H](C)[C@@H](C(=O)O)N(C)C(=O)OCC1=CC=CC=C1

Technology Process of (2S,3S)-2-(((Benzyloxy)carbonyl)(methyl)amino)-3-methylpentanoic acid

There total 6 articles about (2S,3S)-2-(((Benzyloxy)carbonyl)(methyl)amino)-3-methylpentanoic 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: 94.0%

(S)-4-sec-Butyl-5-oxo-oxazolidine-3-carboxylic acid benzyl ester → (S)-2-(Benzyloxycarbonyl-methyl-amino)-3-methyl-pentanoic acid (42417-66-3,42417-67-4,130199-62-1)

Guidance literature:

With chloro-trimethyl-silane; sodium cyanoborohydride; In acetonitrile; for 0.166667h; Ambient temperature;

DOI:10.1246/cl.1999.299

Reference yield: 78.0%

phenylmethyl (4S)-4-[(1S)-1-methylpropyl]-5-oxo-1,3-oxazolidine-3-carboxylate (66866-65-7) → (2S,3S)-3-methyl-2-(methyl{[(phenylmethyl)oxy]carbonyl}amino)pentanoic acid (42417-66-3)

Guidance literature:

With triethylsilane; trifluoroacetic acid; In dichloromethane;

DOI:10.1002/hlca.200690235

Reference yield:

N-Cbz-L-Isoleucine (3160-59-6) → (2S,3S)-3-methyl-2-(methyl{[(phenylmethyl)oxy]carbonyl}amino)pentanoic acid (42417-66-3)

Guidance literature:

Multi-step reaction with 2 steps

1: camphorsulfonic acid / benzene

2: CF₃CO₂H; Et₃SiH

With triethylsilane; camphor-10-sulfonic acid; trifluoroacetic acid; In benzene;

DOI:10.1071/CH06148

upstream raw materials:

N-benzyloxycarbonyl-L-isoleucine

N-Cbz-L-Isoleucine

methyl iodide

phenylmethyl (4S)-4-[(1S)-1-methylpropyl]-5-oxo-1,3-oxazolidine-3-carboxylate

Downstream raw materials:

N-{(2R,3R)-3-methoxy-3-[(2S)-1-{(3R,4S,5S)-3-methoxy-5-methyl-4-[methyl(L-valyl)amino]heptanoyl]pyrrolidin-2-yl]-2-methylpropanoyl]-L-phenylalanine

pentafluorophenyl (3R,4S,5S)-4-[{N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-valyl}(methyl)amino]-3-methoxy-5-methylheptanoate

Refernces

• 1、 Aurelio, Luigi,Brownlee, Robert T. C.,Dang, Jason,Hughes, Andrew B.,Polya, Gideon M.. "Determination of the complete absolute configuration of petriellin A". . p. 407 - 414. Retrieved 2008/02/04.
• 2、 Pettit,Singh,Srirangam,Hogan-Pierson,Williams. "The dolastatins. 19. Synthesis of dolaisoleuine". . p. 1796 - 1800. Retrieved 2007/10/02.