(S)-4-(Benzyloxy)-2-((tert-butoxycarbonyl)amino)butanoic acid

Base Information

• Chemical Name: (S)-4-(Benzyloxy)-2-((tert-butoxycarbonyl)amino)butanoic acid
• CAS No.: 59408-74-1
• Molecular Formula: C16H23 N O5
• Molecular Weight: 309.362
• Hs Code.: 2924299090
• DSSTox Substance ID: DTXSID80567661
• Nikkaji Number: J2.512.938E
• Wikidata: Q72510066
• Mol file: 59408-74-1.mol

Synonyms:59408-74-1;boc-hse(bzl)-oh;Boc-HomoSer(Bzl)-OH;Boc-Hoser(Bzl)-OH;Boc-O-benzyl-L-homoserine;(S)-4-(Benzyloxy)-2-((tert-butoxycarbonyl)amino)butanoic acid;O-Benzyl-N-(tert-butoxycarbonyl)-L-homoserine;Homoserine, N-[(1,1-dimethylethoxy)carbonyl]-O-(phenylmethyl)-;(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-4-phenylmethoxybutanoic acid;Boc-L-Hse(Bzl)-OH;N-Boc-O-benzyl-L-homoserine;SCHEMBL955526;DTXSID80567661;RFDXPGUBDAKLDM-ZDUSSCGKSA-N;MFCD00270497;AKOS015911587;AM82565;DS-18583;O-benzyl-N-(tert-butoxycarbonyl)homoserine;n-tert-butoxycarbonyl-o-benzyl-l-homoserine;CS-0127682;C16046;N-alpha-t-Butyloxycarbonyl-O-benzyl-L-homoserine;(S)-4-benzyloxy-2-tertbutoxycarbonylaminobutyric acid;(S)-4-benzyloxy-2-tert butoxycarbonylamino butyric acid;(S)-4-Benzyloxy-2-tert-butoxycarbonylamino-butyric acid;(S)-4-(benzyloxy)-2-(tert-butoxycarbonylamino)butanoic acid

Chemical Property of (S)-4-(Benzyloxy)-2-((tert-butoxycarbonyl)amino)butanoic acid

Chemical Property:

• Vapor Pressure: 4.82E-10mmHg at 25°C
• Boiling Point: 480.5°C at 760 mmHg
• Flash Point: 244.4°C
• PSA: 84.86000
• Density: 1.154
• LogP: 2.96210
• Storage Temp.: Store at 0-5°C
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 9
• Exact Mass: 309.15762283
• Heavy Atom Count: 22
• Complexity: 358

Purity/Quality:

98%Min ^*data from raw suppliers

Boc-O-benzyl-L-homoserine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CCOCC1=CC=CC=C1)C(=O)O
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@@H](CCOCC1=CC=CC=C1)C(=O)O

Technology Process of (S)-4-(Benzyloxy)-2-((tert-butoxycarbonyl)amino)butanoic acid

There total 4 articles about (S)-4-(Benzyloxy)-2-((tert-butoxycarbonyl)amino)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: 96.0%

4-benzyloxy-(2S)-tert-butoxycarbonylaminobutanoic acid benzyl ester → (S)-2-((tert-butoxy)carbonylamino)-4-(phenylmethoxy)butyric acid (59408-74-1,150009-60-2)

Guidance literature:

With ammonium acetate; hydrogen; palladium on activated charcoal; In methanol; for 20h; Ambient temperature;

DOI:10.1016/0040-4039(95)00527-J

Reference yield:

N-(tert-butyloxycarbonyl) azide (1070-19-5) → (S)-2-((tert-butoxy)carbonylamino)-4-(phenylmethoxy)butyric acid (59408-74-1,150009-60-2)

Guidance literature:

Multi-step reaction with 2 steps

1: MgO / H₂O; dioxane

2: (i) Na, liq. NH₃, (ii) /BRN= 385801/

With magnesium oxide; In 1,4-dioxane; water;

Reference yield:

L-2-(tert-butyloxycarbonylamino)-4-hydroxybutyric acid (41088-86-2) + benzyl bromide (100-39-0) → (S)-2-((tert-butoxy)carbonylamino)-4-(phenylmethoxy)butyric acid (59408-74-1,150009-60-2)

Guidance literature:

Multistep reaction; (i) Na, liq. NH₃, (ii) /BRN= 385801/;

upstream raw materials:

L-2-(tert-butyloxycarbonylamino)-4-hydroxybutyric acid

benzyl bromide

N-(tert-butyloxycarbonyl) azide

Downstream raw materials:

methyl O-benzyl-N-(tert-butoxycarbonyl)-L-homoserinate

N-Methoxy-N-methyl 4-benzyloxy-2(S)-(tert-butoxycarbonylamino)butanamide

Refernces

• 1、 Sajiki, Hironao. "Selective Inhibition of Benzyl Ether Hydrogenolysis with Pd/C Due to the Presence of Ammonia, Pyridine or Ammonium Acetate". . p. 3465 - 3468. Retrieved 2007/10/02.