tert-Butyl ((2S,4S,5S)-5-amino-4-hydroxy-1,6-diphenylhexan-2-yl)carbamate

Base Information

• Chemical Name: tert-Butyl ((2S,4S,5S)-5-amino-4-hydroxy-1,6-diphenylhexan-2-yl)carbamate
• CAS No.: 144163-85-9
• Molecular Formula: C23H32N2O3
• Molecular Weight: 384.519
• European Community (EC) Number: 685-103-4
• UNII: 0N59F56PQ6
• DSSTox Substance ID: DTXSID10932247
• Nikkaji Number: J1.631.162F
• Wikidata: Q72437979
• Mol file: 144163-85-9.mol

Synonyms:144163-85-9;tert-Butyl ((2S,4S,5S)-5-amino-4-hydroxy-1,6-diphenylhexan-2-yl)carbamate;[(1S,3S,4S)-4-Amino-3-hydroxy-5-phenyl-1-(phenylmethyl)pentyl]-carbamic acid 1,1-dimethylethyl ester;(2S,3S,5S)-2-AMINO-3-HYDROXY-5-(TERT-BUTYLOXYCARBONYLAMINO)-1,6-DIPHENYLHEXANE;tert-butyl N-[(2S,4S,5S)-5-amino-4-hydroxy-1,6-diphenylhexan-2-yl]carbamate;0N59F56PQ6;A-88820;[(1S,3S,4S)-4-Amino-3-hydroxy-5-phenyl-1-(phenylmethyl)pentyl]carbamic acid 1,1-dimethyl ethyl ester;Carbamic acid, N-[(1S,3S,4S)-4-amino-3-hydroxy-5-phenyl-1-(phenylmethyl)pentyl]-, 1,1-dimethylethyl ester;Carbamic acid,[(1s,2s,4s)-4-amino-3-Hydroxy-5-phenyl-1-phenylmethyl]pentyl-1,1-dimethylethyl ester;5-tert-Butyloxycarbonylamino-2-amino-3-hydroxy-1,6-diphenylhexane, (2S,3S,5S)-;tert-Butyl (2S,4S,5S)-N-(4-amino-1-benzyl-3-hydroxy-5-phenylpentyl)carbamate;Carbamic acid, N-((1S,3S,4S)-4-amino-3-hydroxy-5-phenyl-1-(phenylmethyl)pentyl)-, 1,1-dimethylethyl ester;UKFHOTNATOJBKZ-ACRUOGEOSA-N;C23H32N2O3;UNII-0N59F56PQ6;SCHEMBL2059435;DTXSID10932247;(2S,4S,5S)-5-Amino-2-(Boc-amino)-4-hydroxy-1,6-diphenylhexane;MFCD09833420;AKOS015841346;AKOS015896454;DS-0823;CS-0130712;A808183;[2S,3S,5S]-2-Amino-3-hydroxy-5-t-butyloxycarbonylamino-1,6-diphenylhexane;tert-butyl (1S,3S,4S)-1-benzyl-3-hydroxy-5-phenyl-4-amino-pentylcarbamate;tert-butyl (1s,3s,4s)-4-amino-1-benzyl-3-hydroxy-5-phenylpentylcarbamate;tert-Butyl((2S,4S,5S)-5-amino-4-hydroxy-1,6-diphenylhexan-2-yl)carbamate;tert-butyl(1S,3S,4S)-1-benzyl-3-hydroxy-5-phenyl-4-amino-pentylcarbamate;tert-butyl(1s,3s,4s)-4-amino-1-benzyl-3-hydroxy-5-phenylpentylcarbamate;(2S, 3S, 5S)-2-Amino-3-hydroxy-5-(t-butyloxycarbonylamino)-1,6-diphenylhexane;(2S,3S,5S)-2-amino-3-hydroxy-5-(t-butyloxycarbonylamino)-1,6-diphenylhexane;(2S,3S,5S)-2-amino-3-hydroxy-5-(t-butyloxycarbonylamino)-1.6-diphenylhexane;(2S,3S,5S)-2-amino-5-[N-(tert-butyloxycarbonyl)amino]-1,6-diphenyl-3-hydroxy hexane;tert-Butyl hydrogen (5-amino-4-hydroxy-1,6-diphenylhexan-2-yl)carbonimidate;[(1S,3S,4S)-4-Amino-3-hydroxy-5-phenyl-1-(phenyl-methyl)pentyl]carbamic acid 1,1-dimethyl ethyl ester;[(1S,3S,4S)-4-amino-3-hydroxy-5-phenyl-1-(phenylmethyl)pentyl]-carbamic acid 1,1-dimethylethyl ester, AldrichCPR

Chemical Property of tert-Butyl ((2S,4S,5S)-5-amino-4-hydroxy-1,6-diphenylhexan-2-yl)carbamate

Chemical Property:

• Appearance/Colour: Powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 71-74°C
• Refractive Index: 1.562
• Boiling Point: 569.182 °C at 760 mmHg
• PKA: 12.35±0.46(Predicted)
• Flash Point: 298.03 °C
• PSA: 84.58000
• Density: 1.111 g/cm³
• LogP: 4.53460
• Storage Temp.: Refrigerator
• 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:

99.9% ^*data from raw suppliers

(2S,3S,5S)-2-Amino-3-hydroxy-5-(tert-butyloxycarbonylamino)-1,6-diphenylhexane ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CC1=CC=CC=C1)CC(C(CC2=CC=CC=C2)N)O
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@@H](CC1=CC=CC=C1)C[C@@H]([C@H](CC2=CC=CC=C2)N)O
• Uses: An Intermediate in the synthesis of lopinavir and ritonavir.

Technology Process of tert-Butyl ((2S,4S,5S)-5-amino-4-hydroxy-1,6-diphenylhexan-2-yl)carbamate

There total 10 articles about tert-Butyl ((2S,4S,5S)-5-amino-4-hydroxy-1,6-diphenylhexan-2-yl)carbamate 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: 92.0%

(2S,3S,5S)-2-(N,N-dibenzylamino)-3-hydroxy-5-(t-butyloxycarbonylamino)-1,6-diphenylhexane (162849-93-6) → (2S,3S,5S)-2-amino-3-hydroxy-5-(t-butyloxycarbonylamino)-1,6-diphenylhexane (144163-85-9)

Guidance literature:

With palladium on activated charcoal; ammonium formate; at 66 ℃; for 2.5h; under 3750.38 Torr; Autoclave;

Reference yield: 72.0%

→ (2S,3S,5S)-2-amino-3-hydroxy-5-(t-butyloxycarbonylamino)-1,6-diphenylhexane (144163-85-9)

Guidance literature:

Reference yield:

(2S,3S,5S)-2-amino-3-hydroxy-5-tert-butoxycarbonylamino-1,6-diphenylhexane succinate (256328-84-4,183388-64-9) → (2S,3S,5S)-2-amino-3-hydroxy-5-(t-butyloxycarbonylamino)-1,6-diphenylhexane (144163-85-9)

Guidance literature:

With sodium hydrogencarbonate; In water; ethyl acetate; for 0.5h;

upstream raw materials:

(2S,3S,5S)-2-(N,N-dibenzylamino)-3-hydroxy-5-(t-butyloxycarbonylamino)-1,6-diphenylhexane

di-tert-butyl dicarbonate

(2S,3S,5S)-2-(N,N-dibenzylamino)-3-hydroxy-5-amino-1,6-diphenylhexane

(2S,3S,5S)-2-amino-3-hydroxy-5-tert-butoxycarbonylamino-1,6-diphenylhexane succinate

Downstream raw materials:

(2S,3S,5S)-2-(2,6-dimethylphenoxyacetyl)amino-3-hydroxy-5-(t-butyloxycarbonylamino)-1,6-diphenylhexane

(2S,3S,5S)-5-(t-butyloxycarbonylamino)-2-(N-((5-thiazolyl)methoxycarbonyl)amino)-3-hydroxy-1,6-diphenylhexane

methyl (1S)-1-[({(1S,2S,4S)-1-benzyl-4-[(tert-butoxycarbonyl)amino]-2-hydroxy-5-phenylpentyl}amino)carbonyl]-2,2-dimethylpropylcarbamate

(2S,3S,5S)-5-Amino-2-(N-((5-thiazolyl)-methoxycarbonyl)amino)-3-hydroxy-1,6-diphenylhexane

Refernces

• 1、 -. "Sulfonamide compound and preparation method and application thereof (by machine translation)". Paragraph 0071; 0080. . Retrieved 2020/12/29.
• 2、 DeGoey, David A.,Grampovnik, David J.,Flentge, Charles A.,Flosi, William J.,Chen,Yeung, Clinton M.,Randolph, John T.,Klein, Larry L.,Dekhtyar, Tatyana,Colletti, Lynn,Marsh, Kennan C.,Stoll, Vincent,Mamo, Mulugeta,Morfitt, David C.,Nguyen, Bach,Schmidt, James M.,Swanson, Sue J.,Mo, Hongmei,Kati, Warren M.,Molla, Akhteruzzaman,Kempf, Dale J.. "2-pyridyl P1'-substituted symmetry-based human immunodeficiency virus protease inhibitors (A-792611 and A-790742) with potential for convenient dosing and reduced side effects". supporting information; experimental part. p. 2571 - 2586. Retrieved 2010/02/28.