H-D-Asp(OtBu)-OH

Base Information

• Chemical Name: H-D-Asp(OtBu)-OH
• CAS No.: 64960-75-4
• Molecular Formula: C8H15NO4
• Molecular Weight: 189.211
• Hs Code.: 2922509090
• European Community (EC) Number: 867-820-6
• DSSTox Substance ID: DTXSID80427039
• Mol file: 64960-75-4.mol

Synonyms:H-D-Asp(OtBu)-OH;64960-75-4;D-ASPARTIC ACID 4-TERT-BUTYL ESTER;(2R)-2-amino-4-(tert-butoxy)-4-oxobutanoic acid;(2R)-2-amino-4-[(2-methylpropan-2-yl)oxy]-4-oxobutanoic acid;(2R)-2-azaniumyl-4-[(2-methylpropan-2-yl)oxy]-4-oxobutanoate;(R)-2-Amino-4-(tert-butoxy)-4-oxobutanoic acid;(2R)-2-amino-4-tert-butoxy-4-oxo-butanoic acid;SCHEMBL38111;DTXSID80427039;AMY31273;MFCD00077101;AKOS006282321;AC-8649;CS-W015949;HY-W015233;AC-19192;AS-17647;EN300-172592;P15797;A834921;Q-102719;Z1198150106

Chemical Property of H-D-Asp(OtBu)-OH

Chemical Property:

• Boiling Point: 318.7 °C at 760 mmHg
• PKA: 2.19±0.23(Predicted)
• Flash Point: 146.5 °C
• PSA: 89.62000
• Density: 1.162 g/cm³
• LogP: 0.83040
• Storage Temp.: Store at 0°C
• XLogP3: -1.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 189.10010796
• Heavy Atom Count: 13
• Complexity: 207

Purity/Quality:

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

D-AsparticAcid4-(1,1-Dimethylethyl)Ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)CC(C(=O)O)N
• Isomeric SMILES: CC(C)(C)OC(=O)C[C@H](C(=O)O)N
• Uses: D-Aspartic Acid 4-(1,1-Dimethylethyl) Ester is a protected form of D-Aspartic Acid (A790020), a non-essential amino acid found in food sources. Its conjugate base D-aspartate has potential use as a a therapeutic agent in the treatment of schizophrenia-related symptoms.

Technology Process of H-D-Asp(OtBu)-OH

There total 2 articles about H-D-Asp(OtBu)-OH 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: 82.0%

tert-butyl (R)-3-(carbo-tert-butoxy)-2-aminopropanoate → (2R)-2-amino-4-tert-butoxy-4-oxobutanoic acid (64960-75-4)

Guidance literature:

With potassium phosphate buffer; In methanol; for 18h; Ambient temperature; porcine liver esterase;

DOI:10.1021/jo00129a066

Reference yield:

bromoacetic acid tert-butyl ester (5292-43-3) + glycine (56-40-6,18875-39-3,25718-94-9) → (2R)-2-amino-4-tert-butoxy-4-oxobutanoic acid (64960-75-4)

Guidance literature:

Multistep reaction;

DOI:10.1021/ja035465e

Reference yield: 24.0%

bromobenzene (108-86-1,52753-63-6) + (2R)-2-amino-4-tert-butoxy-4-oxobutanoic acid (64960-75-4) → 4-tert-butyl 1-methyl 2-(4-oxo-N-phenylbutanamido)succinate (1351467-75-8)

Guidance literature:

bromobenzene; (2R)-2-amino-4-tert-butoxy-4-oxobutanoic acid; With potassium phosphate; 2-(N,N-dimethylamino)ethanol; In water; at 96 ℃; for 46h; Inert atmosphere;

With hydrogenchloride; In water; pH=4 - 5;

upstream raw materials:

bromoacetic acid tert-butyl ester

glycine

Downstream raw materials:

(R)-4-tert-butoxy-2-(4-methylphenylsulfonamido)-4-oxobutanoic acid

4-tert-butyl 1-methyl 2-(4-oxo-N-phenylbutanamido)succinate

C₁₆H₂₂ClNO₆S

(R)-tert-butyl 4-(2,2-dimethoxyethylamino)-3-(4-methylphenylsulfonamido)-4-oxobutanoate

Refernces

• 1、 Stein, Karin A.,Toogood, Peter L.. "Enzyme-Catalyzed Regioselective Hydrolysis of Aspartate Diesters". . p. 8110 - 8112. Retrieved 2007/10/03.