(2S,3S,5S)-1,6-Diphenyl-2-(tert-butoxycarbonylamino)-5-amino-3-hexanol

Base Information

• Chemical Name: (2S,3S,5S)-1,6-Diphenyl-2-(tert-butoxycarbonylamino)-5-amino-3-hexanol
• CAS No.: 144163-88-2
• Molecular Formula: C23H32N2O3
• Molecular Weight: 384.519
• DSSTox Substance ID: DTXSID801120776
• Nikkaji Number: J1.490.909E
• Mol file: 144163-88-2.mol

Synonyms:SCHEMBL5371202;SDSHSQZUSKPIDM-ACRUOGEOSA-N;DTXSID801120776;(2S,3S,5S)-1,6-Diphenyl-2-(tert-butoxycarbonylamino)-5-amino-3-hexanol;(2S, 3S, 5S)-2-tert-butoxycarbonylamino-3-hydroxy-5-amino-1,6-diphenylhexane;(2S,3S,5S)-2-tert-butoxycarbonylamino-3-hydroxy-5-amino-1,6-diphenylhexane;1,1-Dimethylethyl N-[(1S,2S,4S)-4-amino-2-hydroxy-5-phenyl-1-(phenylmethyl)pentyl]carbamate;144163-88-2

Chemical Property of (2S,3S,5S)-1,6-Diphenyl-2-(tert-butoxycarbonylamino)-5-amino-3-hexanol

Chemical Property:

• XLogP3: 3.8
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 10
• Exact Mass: 384.24129289
• Heavy Atom Count: 28
• Complexity: 451

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CC1=CC=CC=C1)C(CC(CC2=CC=CC=C2)N)O
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@@H](CC1=CC=CC=C1)[C@H](C[C@H](CC2=CC=CC=C2)N)O

Technology Process of (2S,3S,5S)-1,6-Diphenyl-2-(tert-butoxycarbonylamino)-5-amino-3-hexanol

There total 33 articles about (2S,3S,5S)-1,6-Diphenyl-2-(tert-butoxycarbonylamino)-5-amino-3-hexanol 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: 100.0%

tert-butyl (1S,2S,4S)-4-azido-1-benzyl-2-hydroxy-5-phenylpentylcarbamate (482648-05-5) → ((1S,2S,4S)-4-amino-1-benzyl-2-hydroxy-5-phenyl-pentyl)-carbamic acid tert-butyl ester (144163-88-2)

Guidance literature:

With hydrogen; 10percent Pd/C; In methanol; under 760.051 Torr;

DOI:10.1039/b005804l

Reference yield: 33.0%

di-tert-butyl dicarbonate (24424-99-5) + (2S,3S,5S)-3-hydroxy-2,5-bisamino-1,6-diphenylhexane (144163-44-0) → ((1S,2S,4S)-4-amino-1-benzyl-2-hydroxy-5-phenyl-pentyl)-carbamic acid tert-butyl ester (144163-88-2)

Guidance literature:

(2S,3S,5S)-3-hydroxy-2,5-bisamino-1,6-diphenylhexane; With phenylboronic acid; In toluene; Heating / reflux;

di-tert-butyl dicarbonate; In dichloromethane; at 25 ℃; for 18h;

With sodium hydroxide; In dichloromethane; water; for 0.166667h;

Reference yield:

(2R,3R,4S,5S)-5-[N-(tert-butyloxycarbonyl)amino]-2,3-epoxy-4-hydroxy-1,6-diphenylhexane (198208-15-0) → ((1S,2S,4S)-4-amino-1-benzyl-2-hydroxy-5-phenyl-pentyl)-carbamic acid tert-butyl ester (144163-88-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 65 percent / RedAl / tetrahydrofuran

2: MsCl; DIPEA / 1,2-dichloro-ethane / 80 °C

3: NaN₃; 18-crown-6 / dimethylsulfoxide

4: NaH / tetrahydrofuran

5: Cs₂CO₃ / methanol; H₂O

6: H₂ / Pd/C

With sodium azide; 18-crown-6 ether; hydrogen; sodium hydride; caesium carbonate; methanesulfonyl chloride; N-ethyl-N,N-diisopropylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; palladium on activated charcoal; In tetrahydrofuran; methanol; water; dimethyl sulfoxide; 1,2-dichloro-ethane;

DOI:10.1016/j.bmc.2003.08.004

upstream raw materials:

(2S,4S,5S)-2-<<(phenylmethoxy)carbonyl>amino>-5-<<(1,1-dimethylethoxy)carbonyl>amino>-1,6-diphenyl-4-hydroxyhexane

tert-butyl (1S,2S,4S)-4-azido-1-benzyl-2-hydroxy-5-phenylpentylcarbamate

[1-benzyl-2-hydroxy-4-(4-methoxy-phenylamino)-5-phenyl-pentyl]-carbamic acid tert-butyl ester

tert-butyl (2S,3S)-3-hydroxy-5-oxo-1,6-diphenylhexan-2-ylcarbamate

Downstream raw materials:

(2S,3S,5S)-3-hydroxy-2,5-bisamino-1,6-diphenylhexane