(2S,3R)-2-Acetamido-3-(tert-butoxy)butanoic acid

Base Information

• Chemical Name: (2S,3R)-2-Acetamido-3-(tert-butoxy)butanoic acid
• CAS No.: 163277-80-3
• Molecular Formula: C10H19 N O4
• Molecular Weight: 217.265
• DSSTox Substance ID: DTXSID70427144
• Wikidata: Q82239863
• ChEMBL ID: CHEMBL1221838
• Mol file: 163277-80-3.mol

Synonyms:163277-80-3;(2S,3R)-2-Acetamido-3-(tert-butoxy)butanoic acid;AC-THR(TBU)-OH;(2S,3R)-2-acetamido-3-[(2-methylpropan-2-yl)oxy]butanoic Acid;L-Threonine, N-acetyl-O-(1,1-dimethylethyl)-;N-Acetyl-O-tert-butyl-L-threonine;Acetyl-O-tert-butyl-L-threonine;(2S,3R)-2-Acetamido-3-(tert-butoxy)butanoicacid;Ac-Thr(tBu)-OH, AldrichCPR;CHEMBL1221838;DTXSID70427144;MFCD00236771;AKOS015910118;AKOS015999019;DS-17080;CS-0158245;C73147;L-Threonine,N-acetyl-O-(1,1-dimethylethyl)-;EN300-2291215;(2S,3R)-3-(TERT-BUTOXY)-2-ACETAMIDOBUTANOIC ACID

Chemical Property of (2S,3R)-2-Acetamido-3-(tert-butoxy)butanoic acid

Chemical Property:

• Melting Point: 137°C
• Boiling Point: 395.4±37.0 °C(Predicted)
• PKA: 3.31±0.10(Predicted)
• PSA: 75.63000
• Density: 1.079±0.06 g/cm3(Predicted)
• LogP: 1.17020
• Storage Temp.: 2-8°C
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 217.13140809
• Heavy Atom Count: 15
• Complexity: 244

Purity/Quality:

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

Ac-Thr(tBu)-OH ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of (2S,3R)-2-Acetamido-3-(tert-butoxy)butanoic acid

There total 2 articles about (2S,3R)-2-Acetamido-3-(tert-butoxy)butanoic 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: 90.0%

(O-tert-butyl)-L-threonine (4378-13-6,201353-89-1) + acetic anhydride (108-24-7) → N-acetyl-O-(tert-butyl)-L-threonine (163277-80-3)

Guidance literature:

With sodium hydroxide; at 0 ℃; for 1.5h;

DOI:10.1016/S0040-4020(97)00059-8

Reference yield:

(O-tert-butyl)-L-threonine (4378-13-6,201353-89-1) + acetic acid (64-19-7,77671-22-8) → N-acetyl-O-(tert-butyl)-L-threonine (163277-80-3)

Guidance literature:

acetic acid; With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; for 0.0833333h;

(O-tert-butyl)-L-threonine; With dmap; In dichloromethane; N,N-dimethyl-formamide; at 30 ℃; for 3h;

DOI:10.1002/ejoc.201901459

Reference yield:

L-Asn(Trt) (132388-59-1) + N-acetyl-O-(tert-butyl)-L-threonine (163277-80-3) → Ac-T(Tyr(C4F9))PN-NH2

Guidance literature:

Multi-step reaction with 2 steps

1.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / 24 h / 20 °C

2.1: tetrafluoroboric acid; sodium nitrite / methanol / 2 h

2.2: 18 h / 45 °C

With tetrafluoroboric acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; sodium nitrite; In methanol;

DOI:10.1021/acs.orglett.6b02858

upstream raw materials:

(O-tert-butyl)-L-threonine

acetic anhydride

acetic acid

Refernces

• 1、 Lloyd-Williams, Paul,Sanchez, Agusti,Carulla, Natalia,Ochoa, Teresa,Giralt, Ernest. "Synthetic studies on threonines. The preparation of protected derivatives of D-allo- and L-allo-threonine for peptide synthesis". . p. 3369 - 3382. Retrieved 2007/10/03.