(2S)-5-[(2-methylpropan-2-yl)oxy]-2-[(2-methylpropan-2-yl)oxycarbonylamino]-5-oxopentanoic acid

Base Information

• Chemical Name: (2S)-5-[(2-methylpropan-2-yl)oxy]-2-[(2-methylpropan-2-yl)oxycarbonylamino]-5-oxopentanoic acid
• CAS No.: 13726-84-6
• Molecular Formula: C14H25NO6
• Molecular Weight: 303.356
• Hs Code.: 2924 19 00
• NSC Number: 164048
• Mol file: 13726-84-6.mol

Synonyms:1370749-29-3;(2S)-5-[(2-methylpropan-2-yl)oxy]-2-[(2-methylpropan-2-yl)oxycarbonylamino]-5-oxopentanoic acid;MFCD00038257;Boc-D-glutamic acid 5-tert-butyl ester;NSC164048;DAUNOSAMINEHYDROCHLORIDE;SCHEMBL617475;5-(TERT-BUTOXY)-2-([(TERT-BUTOXY)CARBONYL]AMINO)-5-OXOPENTANOIC ACID;AKOS024373596;NSC-164048;5-[(2-methylpropan-2-yl)oxy]-2-[(2-methylpropan-2-yl)oxycarbonylamino]-5-oxopentanoic acid;SY018827;Boc-L-glutamic acid gamma-tert.butyl ester;FT-0657311;FT-0686529;5-tertbutoxy-2-(t-butoxycarbonylamino)-5-oxopentanoic acid;5-(tert-Butoxy)-2-((tert-butoxycarbonyl)amino)-5-oxopentanoic acid;(4S)-5-[(2-methylpropan-2-yl)oxy]-4-[(2-methylpropan-2-yl)oxycarbonylamino]-5-oxopentanoic acid

Chemical Property of (2S)-5-[(2-methylpropan-2-yl)oxy]-2-[(2-methylpropan-2-yl)oxycarbonylamino]-5-oxopentanoic acid

Chemical Property:

• Appearance/Colour: White to off-white microcrystalline powder
• Vapor Pressure: 2.42E-09mmHg at 25°C
• Melting Point: 102-105 °C
• Refractive Index: 1.47
• Boiling Point: 449.8 °C at 760 mmHg
• PKA: 3.82±0.10(Predicted)
• Flash Point: 225.8 °C
• PSA: 101.93000
• Density: 1.121 g/cm³
• LogP: 2.47710
• Storage Temp.: 2-8°C
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 9
• Exact Mass: 303.16818752
• Heavy Atom Count: 21
• Complexity: 391

Purity/Quality:

99% ^*data from raw suppliers

Boc-Glu(OtBu)-OH ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)CCC(C(=O)O)NC(=O)OC(C)(C)C

Technology Process of (2S)-5-[(2-methylpropan-2-yl)oxy]-2-[(2-methylpropan-2-yl)oxycarbonylamino]-5-oxopentanoic acid

There total 12 articles about (2S)-5-[(2-methylpropan-2-yl)oxy]-2-[(2-methylpropan-2-yl)oxycarbonylamino]-5-oxopentanoic 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:

di-tert-butyl dicarbonate (24424-99-5) + L-glutamic acid 5-tert-butyl ester (2419-56-9) → Boc-Glu(OtBu)-OH (13726-84-6)

Guidance literature:

With sodium hydrogencarbonate; In 1,4-dioxane; at 20 ℃; for 20h;

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → (tert-butoxy)carbonyl-D-glutamic acid 5-tert-butyl ester (13726-84-6,104719-63-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 90 percent / NaOCH₃ / methanol

2: NaBH₄ / ethanol / 24 h / 20 °C

3: 80 percent / NaIO₄ / H₂O / 4 °C

4: acetonitrile

5: H₂ / PtO₂

6: NaIO₄, RuO₂

With ruthenium(IV) oxide; sodium tetrahydroborate; sodium periodate; hydrogen; sodium methylate; platinum(IV) oxide; In methanol; ethanol; water; acetonitrile;

DOI:10.1016/S0040-4039(00)88778-X

Reference yield:

N-tert.-butyloxycarbonyl-L-serinal (91103-36-5,157683-97-1) → (tert-butoxy)carbonyl-D-glutamic acid 5-tert-butyl ester (13726-84-6,104719-63-3)

Guidance literature:

Multi-step reaction with 3 steps

1: acetonitrile

2: H₂ / PtO₂

3: NaIO₄, RuO₂

With ruthenium(IV) oxide; sodium periodate; hydrogen; platinum(IV) oxide; In acetonitrile;

DOI:10.1016/S0040-4039(00)88778-X

upstream raw materials:

1,1-dimethylethyl 2,4,5-trichlorophenyl carbonate

Boc-Glu

tert.-Butyloxycarbonyl-L-glutaminsaeure-α-benzylester-γ-tert.-butylester

di-tert-butyl dicarbonate

Downstream raw materials:

tert-butyl N2-(tert-butoxycarbonyl)-N1-{[(5S)-3-(5-{2-fluoro-4-[(5R)-2-oxo-5-(1H-1,2,3-triazol-1-ylmethyl)-1,3-oxazolidin-3-yl]phenyl}pyridin-2-yl)-4,5-dihydroisoxazol-5-yl]methyl}-L-α-glutaminate

C₃₇H₃₉N₅O₈

L-glutamic acid

Boc-Glu(OBu-t)-azoAla-Gly-Gly-OEt

Refernces

• 1、 Giannis,Henk. "Chirospecific synthesis of amino acids, amino aldehydes and amino alcohols from D-glucosamine hydrochloride. A multigram synthesis of N-BOC-L-serinal". . p. 1253 - 1256. Retrieved 2007/10/02.