AC-Ser(tbu)-OH

Base Information

• Chemical Name: AC-Ser(tbu)-OH
• CAS No.: 77285-09-7
• Molecular Formula: C₉H₁₇NO₄
• Molecular Weight: 203.238
• Hs Code.: 2924199090
• DSSTox Substance ID: DTXSID10427143
• Wikidata: Q82239861
• ChEMBL ID: CHEMBL1221836
• Mol file: 77285-09-7.mol

Synonyms:AC-SER(TBU)-OH;77285-09-7;(2S)-2-acetamido-3-[(2-methylpropan-2-yl)oxy]propanoic Acid;(2S)-3-(TERT-BUTOXY)-2-ACETAMIDOPROPANOIC ACID;L-Serine,N-acetyl-O-(1,1-dimethylethyl)-;Acetyl-O-tert-butyl-L-serine;Ac-L-Ser(tBu)-OH;N-Acetyl-O-t-butyl-L-serine;Ac-Ser(tBu)-OH, AldrichCPR;SCHEMBL9725956;CHEMBL1221836;DTXSID10427143;N-Acetyl-O-(tert-butyl)-L-serine;MFCD00236770;AKOS025289407;AG-H-08898;N-ACETYL-O-TERT-BUTYL-L-SERINE;AS-64767;N-Acetyl-O-(1,1-dimethylethyl)-L-serine;CS-0208963;D95783;(S)-2-Acetamido-3-(tert-butoxy)propanoic acid;EN300-2166979

Chemical Property of AC-Ser(tbu)-OH

Chemical Property:

• PSA: 75.63000
• LogP: 0.78170
• Storage Temp.: -15°C
• XLogP3: 0
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 203.11575802
• Heavy Atom Count: 14
• Complexity: 219

Purity/Quality:

99% ^*data from raw suppliers

Ac-ser(tbu)-oh ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NC(COC(C)(C)C)C(=O)O
• Isomeric SMILES: CC(=O)N[C@@H](COC(C)(C)C)C(=O)O

Technology Process of AC-Ser(tbu)-OH

There total 2 articles about AC-Ser(tbu)-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: 88.0%

(S)-O-tert-butylserine (18822-58-7,29435-39-0) + acetic anhydride (108-24-7) → N-acetyl-L-serine tert-butyl ether (77285-09-7)

Guidance literature:

In tetrahydrofuran; water; at 20 ℃; for 24h;

DOI:10.1002/psc.2702

Reference yield:

D-serine methyl ester (2104-89-4,2788-84-3,24184-43-8) + diethoxyltriphenylphosphorane (86852-11-1,18509-25-6) + acetic anhydride (108-24-7) + tert-butyl alcohol (75-65-0) → (R)-2-acetamido-3-tert-butoxypropionic acid (125730-23-6,77285-09-7)

Guidance literature:

D-serine methyl ester; diethoxyltriphenylphosphorane; With Triphenylphosphine oxide; In acetonitrile; at 20 ℃; for 24h;

acetic anhydride; With dmap; triethylamine; In dichloromethane; at 20 ℃; for 0.75h;

tert-butyl alcohol; Further stages;

DOI:10.1016/j.bmc.2008.08.055

Reference yield:

N-acetyl-L-serine tert-butyl ether (77285-09-7) → tert-butyl ((S)-2-(((S)-2-((S)-2-acetamido-3-(tert-butoxy)propanamido)-4-(tert-butoxy)-4-oxobutanamido)oxy)-6-(((benzyloxy)carbonyl)amino)hexanoyl)-L-prolinate

Guidance literature:

Multi-step reaction with 3 steps

1.1: thionyl chloride / dichloromethane / 0.17 h / 25 °C

1.2: 3 h

2.1: triethylamine / water; acetonitrile / 48 h / 25 °C

3.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 12 h / 25 °C

With thionyl chloride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; water; acetonitrile;

DOI:10.1002/psc.2702

upstream raw materials:

(S)-O-tert-butylserine

acetic anhydride

D-serine methyl ester

diethoxyltriphenylphosphorane

Refernces

• 1、 Li, Zhiliang,Lebedyeva, Iryna,Zhao, Deqian,Myers, Lauren,Pillai, Girinath G.,Hall, Charles Dennis,Katritzky, Alan R.. "Synthesis of l-lys-aminoxy-goralatide". . p. 923 - 927. Retrieved 2015/02/05.
• 2、 Morieux, Pierre,Stables, James P.,Kohn, Harold. "Synthesis and anticonvulsant activities of N-benzyl (2R)-2-acetamido-3-oxysubstituted propionamide derivatives". experimental part. p. 8968 - 8975. Retrieved 2009/04/06.