(2S)-4-[[(Tert-butoxy)carbonyl]amino]-2-hydroxybutanoic acid

Base Information

• Chemical Name: (2S)-4-[[(Tert-butoxy)carbonyl]amino]-2-hydroxybutanoic acid
• CAS No.: 207305-60-0
• Molecular Formula: C9H17 N O5
• Molecular Weight: 219.238
• European Community (EC) Number: 692-101-7
• Nikkaji Number: J2.910.844G
• Mol file: 207305-60-0.mol

Synonyms:207305-60-0;(2S)-4-[[(TERT-BUTOXY)CARBONYL]AMINO]-2-HYDROXYBUTANOIC ACID;Butanoic acid, 4-[[(1,1-dimethylethoxy)carbonyl]amino]-2-hydroxy-, (2S)- (9CI);(2S)-2-hydroxy-4-[(2-methylpropan-2-yl)oxycarbonylamino]butanoic Acid;(S)-4-((tert-butoxycarbonyl)amino)-2-hydroxybutanoic acid;(2S)-4-{[(tert-butoxy)carbonyl]amino}-2-hydroxybutanoic acid;(S)-4-(Boc-amino)-2-hydroxybutanoic Acid;SCHEMBL570909;(S)-4-(tert-butoxycarbonylamino)-2-hydroxybutanoic acid;POASMXSJVKADPM-LURJTMIESA-N;AC9724;AKOS025149651;N-Boc-(S)-4-amino-2-hydroxybutanoic acid;CS-0518699;EN300-1589650;(S)-4-(tert-Butoxycarbonylamino)-2-hydroxybutyric Acid;(2S)-4-[(tert-butoxycarbonyl)amino]-2-hydroxybutanoic acid

Chemical Property of (2S)-4-[[(Tert-butoxy)carbonyl]amino]-2-hydroxybutanoic acid

Chemical Property:

• Boiling Point: 422.8±35.0 °C(Predicted)
• PKA: 3.74±0.10(Predicted)
• PSA: 95.86000
• Density: 1.204±0.06 g/cm3(Predicted)
• LogP: 0.73760
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 219.11067264
• Heavy Atom Count: 15
• Complexity: 233

Purity/Quality:

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

(2S)-4-[[(tert-Butoxy)carbonyl]amino]-2-hydroxybutanoicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NCCC(C(=O)O)O
• Isomeric SMILES: CC(C)(C)OC(=O)NCC[C@@H](C(=O)O)O
• Uses: (S)-4-(tert-Butoxycarbonylamino)-2-hydroxybutyric Acid is an intermediate in the synthesis of Plazomicin Sulfate (P579505), the acidic salt of Plazomicin (P579500). Plazomicin is a neoglycoside antibiotic with activity against a broad range of Gram-positive and Gram-negive pathogens. Plazomicin showed potent in vitro activity against multidrug-resistant Klebsiella pneumoniae and Escherichia coli.

Technology Process of (2S)-4-[[(Tert-butoxy)carbonyl]amino]-2-hydroxybutanoic acid

There total 2 articles about (2S)-4-[[(Tert-butoxy)carbonyl]amino]-2-hydroxybutanoic 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: 98.0%

(S)-4-amino-2-hydroxybutanoic acid (3938-83-8,13477-53-7,31771-40-1,40371-51-5) + di-tert-butyl dicarbonate (24424-99-5) → (S)-4-[(tert-butoxycarbonyl)amino]-2-hydroxybutanoic acid (207305-60-0)

Guidance literature:

With potassium carbonate; In 1,4-dioxane; water; at 20 ℃; for 24h;

DOI:10.1002/ejoc.201001077

Reference yield:

→ (S)-4-[(tert-butoxycarbonyl)amino]-2-hydroxybutanoic acid (207305-60-0)

Guidance literature:

Reference yield: 89.0%

C35H60F3N5O16 + (S)-4-[(tert-butoxycarbonyl)amino]-2-hydroxybutanoic acid (207305-60-0) → C44H75F3N6O20

Guidance literature:

(S)-4-[(tert-butoxycarbonyl)amino]-2-hydroxybutanoic acid; With triethylamine; In N,N-dimethyl-formamide; at 21 ℃; for 0.166667h;

C₃₅H₆₀F₃N₅O₁₆; With N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 21 ℃;

upstream raw materials:

(S)-4-amino-2-hydroxybutanoic acid

di-tert-butyl dicarbonate

Downstream raw materials:

2-benzyloxy-4-tert-butoxycarbonylamino-butyric acid

[3-benzyloxy-3-(methoxy-methyl-carbamoyl)-propyl]-carbamic acid tert-butyl ester

6',2'-diPNZ-3-Boc-1-(N-Boc-4-amino-2(S)-hydroxy-butyryl)-sisomicin

tert-butyl ((2R,3R,4R,5R)-2-(((1S,2S,3R,4S,6R)-4-((tert-butoxycarbonyl)amino)-6-((S)-4-((tert-butoxycarbonyl)amino)-2-hydroxybutanamido)-3-(((2S,3R)-3-((tert-butoxycarbonyl)amino)-6-(((((4-nitrobenzyl)oxy)carbonyl)amino)methyl)-3,4-dihydro-2H-pyran-2-yl)oxy)-2-hydroxycyclohexyl)oxy)-3,5-dihydroxy-5-methyltetrahydro-2H-pyran-4-yl)(methyl)carbamate

Refernces

• 1、 -. "NOVEL ANTIBACTERIAL 3"-DERIVATIVES OF 4,6-DISUBSTITUTED 2,5-DIDEOXYSTREPTAMINE AMINOGLYCOSIDE ANTIBIOTICS". Page/Page column 198; 229. . Retrieved 2020/07/05.
• 2、 -. "STIMULUS-RESPONSIVE POLY(LACTIC-CO-GLYCOLIC)-BASED POLYMERS AND NANOPARTICLES FORMED THEREFROM". Page/Page column 21. . Retrieved 2016/12/12.