(S)-Isopropyl 2-(((benzyloxy)carbonyl)amino)-5-hydroxypentanoate

Base Information

• Chemical Name: (S)-Isopropyl 2-(((benzyloxy)carbonyl)amino)-5-hydroxypentanoate
• CAS No.: 176237-44-8
• Molecular Formula: C16H23NO5
• Molecular Weight: 309.3575
• Hs Code.: 2924299090
• DSSTox Substance ID: DTXSID70452315
• Wikidata: Q72481067
• Mol file: 176237-44-8.mol

Synonyms:176237-44-8;(S)-Isopropyl 2-(((benzyloxy)carbonyl)amino)-5-hydroxypentanoate;propan-2-yl (2S)-5-hydroxy-2-(phenylmethoxycarbonylamino)pentanoate;L-Norvaline, 5-hydroxy-N-[(phenylmethoxy)carbonyl]-, 1-methylethyl ester;(S)isopropyl 2-(((benzyloxy)carbonyl)amino)-5-hydroxypentanoate;isopropyl (S)-2-(((benzyloxy)carbonyl)amino)-5-hydroxypentanoate;AC-7895;DTXSID70452315;SPCNGEWBZXQKHY-AWEZNQCLSA-N;AKOS015902319;N-benzoxycarbonyl-5-hydroxy-L-norvaline isoproryl ester;N-benzoxycarbonyl-5-hydroxy-L-norvaline,isoproryl ester;Propan-2-yl N-[(benzyloxy)carbonyl]-5-hydroxy-L-norvalinate;(S)-Isopropyl2-(((benzyloxy)carbonyl)amino)-5-hydroxypentanoate;propan-2-yl (2S)-2-{[(benzyloxy)carbonyl]amino}-5-hydroxypentanoate

Chemical Property of (S)-Isopropyl 2-(((benzyloxy)carbonyl)amino)-5-hydroxypentanoate

Chemical Property:

• Vapor Pressure: 1.21E-09mmHg at 25°C
• Refractive Index: 1.519
• Boiling Point: 470.2 °C at 760 mmHg
• PKA: 11.00±0.46(Predicted)
• Flash Point: 238.1 °C
• PSA: 88.35000
• Density: 1.152 g/cm³
• LogP: 2.20990
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 10
• Exact Mass: 309.15762283
• Heavy Atom Count: 22
• Complexity: 339

Purity/Quality:

99% ^*data from raw suppliers

(S)-Isopropyl2-(((benzyloxy)carbonyl)amino)-5-hydroxypentanoate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)OC(=O)C(CCCO)NC(=O)OCC1=CC=CC=C1
• Isomeric SMILES: CC(C)OC(=O)[C@H](CCCO)NC(=O)OCC1=CC=CC=C1

Technology Process of (S)-Isopropyl 2-(((benzyloxy)carbonyl)amino)-5-hydroxypentanoate

There total 2 articles about (S)-Isopropyl 2-(((benzyloxy)carbonyl)amino)-5-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: 84.0%

N-benzyloxycarbonyl-L-pyroglutamic acid isopropyl ester (176237-43-7) → isopropyl (S)-2-(benzyloxycarbonylamino)-5-hydroxypentanoate (176237-44-8)

Guidance literature:

With sodium tetrahydroborate; potassium dihydrogenphosphate; In methanol; water; at 22 - 32 ℃;

DOI:10.1055/s-1996-4192

Reference yield:

(S)-N-Benzyloxycarbonylpyroglutamic acid chloride (61177-53-5) → isopropyl (S)-2-(benzyloxycarbonylamino)-5-hydroxypentanoate (176237-44-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / pyridine / CH₂Cl₂ / -30 - 20 °C

2: 84 percent / NaBH₄, KH₂PO₄ / methanol; H₂O / 22 - 32 °C

With pyridine; sodium tetrahydroborate; potassium dihydrogenphosphate; In methanol; dichloromethane; water;

DOI:10.1055/s-1996-4192

Reference yield: 100.0%

methanesulfonyl chloride (124-63-0) + isopropyl (S)-2-(benzyloxycarbonylamino)-5-hydroxypentanoate (176237-44-8) → isopropyl (S)-2-(benzyloxycarbonylamino)-5-(methanesulfonyloxy)pentanoate (176237-45-9)

Guidance literature:

With triethylamine; In dichloromethane; at 0 ℃; for 2h;

DOI:10.1055/s-1996-4192

upstream raw materials:

N-benzyloxycarbonyl-L-pyroglutamic acid isopropyl ester

(S)-N-Benzyloxycarbonylpyroglutamic acid chloride

Downstream raw materials:

isopropyl (S)-2-(benzyloxycarbonylamino)-5-(methanesulfonyloxy)pentanoate

isopropyl (S)-1-acetyl-2-benzyloxycarbonylhexahydropyridazine-3-carboxylate

isopropyl (S)-2-(2-acetyl-1-benzyloxycarbonylhydrazino)-5-(methanesulfonyloxy)pentanoate

Refernces