(S)-5-(Allyloxy)-2-((tert-butoxycarbonyl)amino)-5-oxopentanoic acid

Base Information

• Chemical Name: (S)-5-(Allyloxy)-2-((tert-butoxycarbonyl)amino)-5-oxopentanoic acid
• CAS No.: 132286-79-4
• Molecular Formula: C13H21NO6
• Molecular Weight: 287.313
• Hs Code.: 2924199090
• DSSTox Substance ID: DTXSID201152115
• Nikkaji Number: J430.908A
• Mol file: 132286-79-4.mol

Synonyms:132286-79-4;(S)-5-(Allyloxy)-2-((tert-butoxycarbonyl)amino)-5-oxopentanoic acid;Boc-Glu(OAll)-OH;N-alpha-t-Butyloxycarbonyl-L-glutamic acid beta-allyl ester;(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-5-oxo-5-prop-2-enoxypentanoic acid;L-Glutamic acid, N-[(1,1-dimethylethoxy)carbonyl]-, 5-(2-propen-1-yl) ester;Boc-L-glutamic acid-gamma-allyl ester;Boc-L-Glu(OAll)-OH;SCHEMBL2388449;C13H21NO6;(2S)-2-{[(tert-butoxy)carbonyl]amino}-5-oxo-5-(prop-2-en-1-yloxy)pentanoic acid;DTXSID201152115;MFCD00273402;AKOS025146490;FD21389;AS-49056;CS-0157979;(S)-5-(Allyloxy)-2-(boc-amino)-5-oxopentanoic acid;(S)-5-(Allyloxy)-2-((tert-butoxycarbonyl)amino)-5-oxopentanoicacid;(S)-5-(allyloxy)-2-(tert-butoxycarbonylamino)-5-oxopentanoic acid;5-(2-Propen-1-yl) hydrogen N-[(1,1-dimethylethoxy)carbonyl]-L-glutamate;N-alpha-t-Butyloxycarbonyl-L-glutamic acid beta-allyl ester (Boc-L-Glu(OAll)-OH)

Chemical Property of (S)-5-(Allyloxy)-2-((tert-butoxycarbonyl)amino)-5-oxopentanoic acid

Chemical Property:

• Vapor Pressure: 2.75E-09mmHg at 25°C
• Refractive Index: 1.479
• Boiling Point: 448.294 °C at 760 mmHg
• PKA: 3.81±0.10(Predicted)
• Flash Point: 224.92 °C
• PSA: 101.93000
• Density: 1.154 g/cm³
• LogP: 1.86460
• Storage Temp.: Store at 0°C
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 10
• Exact Mass: 287.13688739
• Heavy Atom Count: 20
• Complexity: 372

Purity/Quality:

99% ^*data from raw suppliers

Boc-L-Glu(All)-OH ^*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)OCC=C)C(=O)O
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@@H](CCC(=O)OCC=C)C(=O)O

Technology Process of (S)-5-(Allyloxy)-2-((tert-butoxycarbonyl)amino)-5-oxopentanoic acid

There total 4 articles about (S)-5-(Allyloxy)-2-((tert-butoxycarbonyl)amino)-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: 96.0%

Boc-Glu(OAll)-ONbn (134757-74-7) → N-α-(t-butoxycarbonyl)-L-glutamic γ-allyl ester (132286-79-4,259221-91-5)

Guidance literature:

With tetrabutyl ammonium fluoride; In N,N-dimethyl-formamide; Ambient temperature;

DOI:10.1021/jo00018a052

Reference yield: 86.0%

C16H25NO6 (212569-21-6) → N-α-(t-butoxycarbonyl)-L-glutamic γ-allyl ester (132286-79-4,259221-91-5)

Guidance literature:

With Alcalase-cross-linked-enzyme-aggregates; In tert-butyl alcohol; at 37 ℃; for 16h; pH=7.5; regioselective reaction; aq. phosphate buffer; Enzymatic reaction;

DOI:10.1016/j.tetlet.2009.03.130

Reference yield:

L-glutamic acid (56-86-0,21675-62-7,23009-64-5,25104-13-6,84960-48-5,25513-46-6) → N-α-(t-butoxycarbonyl)-L-glutamic γ-allyl ester (132286-79-4,259221-91-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 77 percent / chlorotrimethylsilane / 12 h / Ambient temperature

2: Et₃N / dioxane / 12 h / Ambient temperature

With chloro-trimethyl-silane; triethylamine; In 1,4-dioxane;

upstream raw materials:

di-tert-butyl dicarbonate

L-glutamic acid γ-allyl ester hydrochloride

Boc-Glu(OAll)-ONbn

L-glutamic acid

Downstream raw materials:

C₂₁H₂₉NO₆S₂

C₂₈H₂₈N₂O₇

benzyl (4S,6R,15S)-6-[(tert-butoxycarbonyl)amino]-11,16-dimethyl-2,2,9,12,17-pentaoxo-2λ⁶-thia-8,11,16-triazatricyclo[16.3.1.0^4,8]docosa-1(22),18,20-triene-15-carboxylate

benzyl (4S,6R,15S)-6-[(tert-butoxycarbonyl)amino]-11,16-dimethyl-9,12,17-trioxo-2-thia-8,11,16-triazatricyclo[16.3.1.0^4,8]docosa-1⁽²²⁾,18,20-triene-15-carboxylate

Refernces

• 1、 Namikoshi, Michio,Kundu, Bijoy,Rinehart, Kenneth L.. "Use of Tetrabutylammonium Fluoride as a Facile Deprotecting Reagent for 4-Nitrobenzyl, 2,2,2-Trichloroethyl, and Phenacyl Esters of Amino Acids". . p. 5464 - 5466. Retrieved 2007/10/02.