tert-butyl 5-benzyloxycarbonylamino-2(S)-tert-butoxycarbonylamino-4(R)-hydroxypentanoate

Base Information

• Chemical Name: tert-butyl 5-benzyloxycarbonylamino-2(S)-tert-butoxycarbonylamino-4(R)-hydroxypentanoate
• CAS No.: 371972-14-4
• Molecular Formula: C25H32N2O7
• Molecular Weight: 438.521
• DSSTox Substance ID: DTXSID80464606
• Nikkaji Number: J1.682.380E
• Wikidata: Q82290000
• Mol file: 371972-14-4.mol

Synonyms:371972-14-4;tert-butyl 5-benzyloxycarbonylamino-2(S)-tert-butoxycarbonylamino-4(R)-hydroxypentanoate;tert-butyl (2S,4R)-4-hydroxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]-5-(phenylmethoxycarbonylamino)pentanoate;LMUZBCCYFRMNHR-SJORKVTESA-N;SCHEMBL1023911;DTXSID80464606;tert-Butyl-(2S,4R)-N?-(benzyloxycarbonyl)-N?-benzyloxycarbonyl)-4-hydroxyornithinate;tert-butyl (4R)-N5-[(benzyloxy)carbonyl]-N2-(tert-butoxycarbonyl)-4-hydroxy-L-ornithinate;tert-Butyl-(2S,4R)-N partial differential-(benzyloxycarbonyl)-N partial differential-benzyloxycarbonyl)-4-hydroxyornithinate

Chemical Property of tert-butyl 5-benzyloxycarbonylamino-2(S)-tert-butoxycarbonylamino-4(R)-hydroxypentanoate

Chemical Property:

• Melting Point: 79-81°C
• Boiling Point: 593.7±50.0 °C(Predicted)
• PKA: 10.98±0.46(Predicted)
• PSA: 130.17000
• Density: 1.154±0.06 g/cm3(Predicted)
• LogP: 3.30760
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 13
• Exact Mass: 438.23660143
• Heavy Atom Count: 31
• Complexity: 590

Purity/Quality:

98% ^*data from raw suppliers

tert-Butyl-(2S,4R)-N?-(benzyloxycarbonyl)-N?-benzyloxycarbonyl)-4-hydroxyornithinate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)C(CC(CNC(=O)OCC1=CC=CC=C1)O)NC(=O)OC(C)(C)C
• Isomeric SMILES: CC(C)(C)OC(=O)[C@H](C[C@H](CNC(=O)OCC1=CC=CC=C1)O)NC(=O)OC(C)(C)C
• Uses: Protected (2S,4R)-4-Hydroxyornithine, which is a nonproteinogenic amino acid that is widely found in nature

Technology Process of tert-butyl 5-benzyloxycarbonylamino-2(S)-tert-butoxycarbonylamino-4(R)-hydroxypentanoate

There total 9 articles about tert-butyl 5-benzyloxycarbonylamino-2(S)-tert-butoxycarbonylamino-4(R)-hydroxypentanoate 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: 83.0%

dibenzyl dicarbonate (31139-36-3) + tert-butyl (2S,4R)-5-amino-2-((tert-butoxycarbonyl)amino)-4-hydroxypentanoate (371972-12-2) → tert-butyl-(2S,4R)-Nα-(tert-butoxycarbonyl)-Nδ-(benzyloxycarbonyl)-4-hydroxy-ornithinate (371972-14-4)

Guidance literature:

In tetrahydrofuran; dichloromethane; at 0 ℃; for 1h;

Reference yield:

N-tert-butoxycarbonyl aspartic acid tert-butyl ester (34582-32-6) → tert-butyl-(2S,4R)-Nα-(tert-butoxycarbonyl)-Nδ-(benzyloxycarbonyl)-4-hydroxy-ornithinate (371972-14-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: N-methylmorpholine; ClCOOEt / tetrahydrofuran / 0.25 h / -5 °C

1.2: NaBH₄ / H₂O / 3.5 h / 20 °C

1.3: 92 percent / aq. HCl / 5 °C / pH 2

2.1: 95 percent / polymer-bound-NMe₃⁽¹⁺⁾*Br(OAc)2^-; TEMPO / CH₂Cl₂ / 16 h / 20 °C

3.1: 15 percent / NaOEt / ethanol / 12 h / 20 °C

4.1: ammonium formate / Pd/C / methanol / 2 h / -10 °C

5.1: 3.3 g / N,N-diisopropylamine / dimethylformamide / 16 h / 20 °C

With 4-methyl-morpholine; 2,2,6,6-tetramethyl-piperidine-N-oxyl; polymer-bound-NMe₃⁽¹⁺⁾*Br(OAc)2^-; sodium ethanolate; ammonium formate; chloroformic acid ethyl ester; diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; 3.1: Henri reaction;

DOI:10.1021/ol016445p

Reference yield:

tert-butyl (2S)-2-[(tert-butoxycarbonyl)amino]-4-oxobutanoate (81323-59-3) → tert-butyl-(2S,4R)-Nα-(tert-butoxycarbonyl)-Nδ-(benzyloxycarbonyl)-4-hydroxy-ornithinate (371972-14-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 15 percent / NaOEt / ethanol / 12 h / 20 °C

2: ammonium formate / Pd/C / methanol / 2 h / -10 °C

3: 3.3 g / N,N-diisopropylamine / dimethylformamide / 16 h / 20 °C

With sodium ethanolate; ammonium formate; diisopropylamine; palladium on activated charcoal; In methanol; ethanol; N,N-dimethyl-formamide; 1: Henri reaction;

DOI:10.1021/ol016445p

upstream raw materials:

N-(Benzyloxycarbonyloxy)succinimide

tert-butyl (2S,4R)-5-amino-2-((tert-butoxycarbonyl)amino)-4-hydroxypentanoate

di-tert-butyl dicarbonate

(R)-5-((S)-2-Amino-2-tert-butoxycarbonyl-ethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester

Downstream raw materials:

tert-butyl (4R)-N₅-[(benzyloxy)carbonyl]-N₂-(tert-butoxycarbonyl)-4-[(methylsulfonyl)oxy]-L-ornithinate

tert-butyl (4R)-N₅-[(benzyloxy)carbonyl]-N₂-(tert-butoxycarbonyl)-4-{[(4-methylphenyl)sulfonyl]oxy}-L-ornithinate

(3S,5R)-[5-(benzyloxycarbonylaminomethyl)-2-oxotetrahydrofuran-3-yl]carbamic acid tert-butyl ester

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