(R)-4-((tert-Butoxycarbonyl)amino)-3-hydroxybutanoic acid

Base Information

• Chemical Name: (R)-4-((tert-Butoxycarbonyl)amino)-3-hydroxybutanoic acid
• CAS No.: 120021-39-8
• Molecular Formula: C₉H₁₇NO₅
• Molecular Weight: 219.238
• Hs Code.: 2924199090
• DSSTox Substance ID: DTXSID70515994
• Nikkaji Number: J2.143.801D
• Wikidata: Q82377182
• Mol file: 120021-39-8.mol

Synonyms:120021-39-8;(R)-4-((tert-Butoxycarbonyl)amino)-3-hydroxybutanoic acid;(R)-4-(BOC-AMINO)-3-HYDROXYBUTANOIC ACID;(R)-(-)-4-N-Boc-Amino-3-Hydroxybutanoic Acid;Butanoic acid, 4-[[(1,1-dimethylethoxy)carbonyl]amino]-3-hydroxy-, (3R)- (9CI);(3R)-3-hydroxy-4-[(2-methylpropan-2-yl)oxycarbonylamino]butanoic acid;Butanoic acid, 4-[[(1,1-dimethylethoxy)carbonyl]amino]-3-hydroxy-, (3R)-;SCHEMBL5708383;AMY6620;DTXSID70515994;VEA02139;MFCD18831554;AKOS022173374;AS-35996;CS-0043480;pound R)-4-Boc-Amino-3-Hydroxybutanoic Acid;EN300-1706652;(R)-4-((tert-Butoxycarbonyl)amino)-3-hydroxybutanoicacid;(3R)-4-{[(tert-butoxy)carbonyl]amino}-3-hydroxybutanoic acid;(3R)-4-[(TERT-BUTOXYCARBONYL)AMINO]-3-HYDROXYBUTANOIC ACID

Chemical Property of (R)-4-((tert-Butoxycarbonyl)amino)-3-hydroxybutanoic acid

Chemical Property:

• PSA: 95.86000
• LogP: 0.73760
• Storage Temp.: 2-8°C
• 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:

99% ^*data from raw suppliers

(R)-4-(Boc-amino)-3-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)NCC(CC(=O)O)O
• Isomeric SMILES: CC(C)(C)OC(=O)NC[C@@H](CC(=O)O)O

Technology Process of (R)-4-((tert-Butoxycarbonyl)amino)-3-hydroxybutanoic acid

There total 5 articles about (R)-4-((tert-Butoxycarbonyl)amino)-3-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: 99.0%

ethyl (3R)-4-(tert-butyloxycarbonyl)amino-3-hydroxybutanoate (181772-51-0) → (R)-4-(tert-butyloxycarbonyl)amino-3-hydroxybutanoic acid (120021-39-8,127852-78-2,69489-07-2)

Guidance literature:

With potassium hydroxide; In ethanol; water; at 20 ℃; for 2h;

DOI:10.1016/j.tet.2009.10.097

Reference yield: 96.0%

(R)-(-)-methyl N-t-butyloxycarbonyl-3-hydroxy-4-aminobutanoate (87554-49-2) → (R)-4-(tert-butyloxycarbonyl)amino-3-hydroxybutanoic acid (120021-39-8,127852-78-2,69489-07-2)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; water; for 1h; Ambient temperature;

DOI:10.1055/s-1992-26123

Reference yield:

tert-butyldicarbonate (34619-03-9) → (R)-4-(tert-butyloxycarbonyl)amino-3-hydroxybutanoic acid (120021-39-8,127852-78-2,69489-07-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 87 percent / H₂ / Pd/C / ethyl acetate / 15 h / Ambient temperature

2: NaOH / methanol

With sodium hydroxide; hydrogen; palladium on activated charcoal; In methanol; ethyl acetate;

DOI:10.1055/s-1999-2651

upstream raw materials:

(R)-(-)-methyl N-t-butyloxycarbonyl-3-hydroxy-4-aminobutanoate

tert-butyldicarbonate

BOC-glycine

methyl 4-[(tert-butoxycarbonyl)amino]-3-oxobutanoate

Downstream raw materials:

(R)-4-<(Benzyloxycarbonyl)amino>-3-hydroxybutanoic acid

methyl (3R,5R)-3-benzyloxycarbonylamino-6-<(E,E)-2,4-hexadienoylamino>-5-hydroxyhexanoate

Sperabillin C

[(2R,4S)-2-(tert-Butoxycarbonylamino-methyl)-6-oxo-tetrahydro-pyran-4-yl]-carbamic acid benzyl ester