(3S)-3-[(2-methylpropan-2-yl)oxycarbonylamino]-6-oxo-6-phenylmethoxyhexanoic acid

Base Information

• Chemical Name: (3S)-3-[(2-methylpropan-2-yl)oxycarbonylamino]-6-oxo-6-phenylmethoxyhexanoic acid
• CAS No.: 218943-30-7
• Molecular Formula: C18H25NO6
• Molecular Weight: 351.4
• Hs Code.: 29242990
• DSSTox Substance ID: DTXSID70402794
• Nikkaji Number: J2.439.270H
• Mol file: 218943-30-7.mol

Synonyms:218943-30-7;Boc-beta-Hoglu(Obzl)-OH;(3S)-3-[(2-methylpropan-2-yl)oxycarbonylamino]-6-oxo-6-phenylmethoxyhexanoic acid;3-[(2-methylpropan-2-yl)oxycarbonylamino]-6-oxo-6-phenylmethoxyhexanoic acid;Boc-beta-HoGlu(OBzl)-OH Boc-L-beta-homoglutamic acid 6-b;Boc-beta-homo-Glu(OBzl)-OH;SCHEMBL18575403;DTXSID70402794;Boc-L-|A-homoglutamic acid(OBzl);Boc-L-beta-homoglutamic acid(OBzl);AKOS032947761;BOC-L-BETA-HOMOGLUTAMICACID(OBZL);FT-0696174;A815738;4-(tert-Butoxycarbonylamino)hexanedioic acid 1-benzyl ester;6-(BENZYLOXY)-3-[(TERT-BUTOXYCARBONYL)AMINO]-6-OXOHEXANOIC ACID;3-[(2-methylpropan-2-yl)oxycarbonylamino]-6-oxidanylidene-6-phenylmethoxy-hexanoic acid;3-[[(2-methylpropan-2-yl)oxy-oxomethyl]amino]-6-oxo-6-phenylmethoxyhexanoic acid

Chemical Property of (3S)-3-[(2-methylpropan-2-yl)oxycarbonylamino]-6-oxo-6-phenylmethoxyhexanoic acid

Chemical Property:

• Vapor Pressure: 4.6E-12mmHg at 25°C
• Refractive Index: 1.52
• Boiling Point: 530 °C at 760 mmHg
• PKA: 4.35±0.10(Predicted)
• Flash Point: 274.4 °C
• PSA: 101.93000
• Density: 1.178 g/cm³
• LogP: 3.26890
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 11
• Exact Mass: 351.16818752
• Heavy Atom Count: 25
• Complexity: 451

Purity/Quality:

98%min ^*data from raw suppliers

Boc-l-β-homoglutamicacid6-benzylester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CCC(=O)OCC1=CC=CC=C1)CC(=O)O
• Uses: Starting materials for peptide synthesis, peptidomimetic and medicinal chemistry, protected amino acids, coupling reagents, linkers and resins, natural and unusual amino acids and building blocks used in peptide synthesis, peptidomimetic and medicinal chemistry. Reagents for PEGylation, Life science Research and biocatalysis. Boc-l-beta-homoglutamic acid 6-benzyl ester

Technology Process of (3S)-3-[(2-methylpropan-2-yl)oxycarbonylamino]-6-oxo-6-phenylmethoxyhexanoic acid

There total 3 articles about (3S)-3-[(2-methylpropan-2-yl)oxycarbonylamino]-6-oxo-6-phenylmethoxyhexanoic 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: 74.0%

4-tert-butoxycarbonylamino-6-diazo-5-oxo-hexanoic acid benzyl ester (128135-31-9) → (3S)-3-tert-butoxycarbonylamino-5-benzyloxycarbonylpentanoic acid (218943-30-7)

Guidance literature:

With 4-methyl-morpholine; water; silver trifluoroacetate; In tetrahydrofuran; at 20 ℃; for 4.5h; Darkness; Cooling with ice;

Reference yield:

Boc-Glu(OBzl)-OH (13574-13-5) → (3S)-3-tert-butoxycarbonylamino-5-benzyloxycarbonylpentanoic acid (218943-30-7)

Guidance literature:

Multi-step reaction with 2 steps

1: ClCO₂Et

2: AgO₂CCF₃

With silver trifluoroacetate; chloroformic acid ethyl ester; 1: Substitution / 1: Substitution / 2: Wolff rearrangement;

DOI:10.1021/ol000122w

Reference yield:

(S)-4-tert-Butoxycarbonylamino-5-ethoxycarbonyloxy-5-oxo-pentanoic acid benzyl ester (147471-66-7) → (3S)-3-tert-butoxycarbonylamino-5-benzyloxycarbonylpentanoic acid (218943-30-7)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrahydrofuran; diethyl ether / 3 h / Ambient temperature

2: 71 percent / H₂O, CF₃CO₂Ag, NEt₃ / tetrahydrofuran / 3 h / -25 - 20 °C

With water; silver trifluoroacetate; triethylamine; In tetrahydrofuran; diethyl ether;

DOI:10.1039/a805478i

upstream raw materials:

4-tert-butoxycarbonylamino-6-diazo-5-oxo-hexanoic acid benzyl ester

Boc-Glu(OBzl)-OH

(S)-4-tert-Butoxycarbonylamino-5-ethoxycarbonyloxy-5-oxo-pentanoic acid benzyl ester

Downstream raw materials:

(S)-5-[(R)-1-Benzyloxymethyl-2-(2,2,2-trichloro-ethoxycarbonyl)-ethylcarbamoyl]-4-tert-butoxycarbonylamino-pentanoic acid benzyl ester

(S)-3-((S)-5-Benzyloxycarbonyl-3-tert-butoxycarbonylamino-pentanoylamino)-hexanedioic acid 6-benzyl ester 1-(2,2,2-trichloro-ethyl) ester

(S)-3-[(S)-5-Benzyloxycarbonyl-3-((S)-5-benzyloxycarbonyl-3-tert-butoxycarbonylamino-pentanoylamino)-pentanoylamino]-hexanedioic acid 6-benzyl ester 1-(2,2,2-trichloro-ethyl) ester

3-(5-benzyloxycarbonyl-3-tert-butoxycarbonylamino-pentanoylamino)-hexanedioic acid 6-benzyl ester 1-(2-oxo-2-phenyl-ethyl) ester

Refernces

• 1、 -. "QUATERNARY ASSEMBLIES OF WATER-SOLUBLE NON-PEPTIDE HELICAL FOLDAMERS, THEIR USE AND PRODUCTION THEREOF". Paragraph 281; 283; 284. . Retrieved 2017/03/21.
• 2、 Cheng, Jianjun,Ziller, Joseph W.,Deming, Timothy J.. "Synthesis of optically active β-amino acid N-carboxyanhydrides". . p. 1943 - 1946. Retrieved 2007/10/03.