[(1S,2R)-3-[[(4-Nitrophenyl)sulfonyl](2-methylpropyl)amino]-2-hydroxy-1-phenylmethyl)propyl]carbamic Acid, (3S)-Tetrahydro-3-furanyl Ester

Base Information

• Chemical Name: [(1S,2R)-3-[[(4-Nitrophenyl)sulfonyl](2-methylpropyl)amino]-2-hydroxy-1-phenylmethyl)propyl]carbamic Acid, (3S)-Tetrahydro-3-furanyl Ester
• CAS No.: 160231-69-6
• Molecular Formula: C25H33N3O8S
• Molecular Weight: 535.618
• European Community (EC) Number: 605-202-8
• DSSTox Substance ID: DTXSID20430966
• Nikkaji Number: J2.018.762J
• Wikidata: Q76411497
• Mol file: 160231-69-6.mol

Synonyms:160231-69-6;[(1S,2R)-3-[[(4-Nitrophenyl)sulfonyl](2-methylpropyl)amino]-2-hydroxy-1-phenylmethyl)propyl]carbamic Acid, (3S)-Tetrahydro-3-furanyl Ester;[(3S)-oxolan-3-yl] N-[(2S,3R)-3-hydroxy-4-[2-methylpropyl-(4-nitrophenyl)sulfonylamino]-1-phenylbutan-2-yl]carbamate;(S)-Tetrahydrofuran-3-yl ((2S,3R)-3-hydroxy-4-(N-isobutyl-4-nitrophenylsulfonamido)-1-phenylbutan-2-yl)carbamate;[(1S,2R)-3-[[(4-Nitrophenyl)sulfonyl](2-methylpropyl)amino]-2-hydroxy-1-phenylmethyl)propyl]carbamic;Carbamic acid, N-[(1S,2R)-2-hydroxy-3-[(2-methylpropyl)[(4-nitrophenyl)sulfonyl]amino]-1-(phenylmethyl)propyl]-, (3S)-tetrahydro-3-furanyl ester;[(1S,2R)-3-[[(4-Nitrophenyl)sulfonyl](2-methylpropyl)amino]-2-hydroxy-1-phenylmethyl)propyl]carbamic Acid, (3S)-Tetrahydro-3-furan-d4-yl Ester;SCHEMBL469815;AMY4342;DTXSID20430966;AKOS015901545;CID 9807180;J-502673;(1S, 2R)-2-hydroxy-3-[(2-methylpropyl) (4-nitrophenylsulfonyl) amino]-1-(phenylmethyl) propylcarbamic acid (S) Ctetrahydro-3-furanyl ester;(3S)-Tetrahydro-3-furanyl N-((1S,2R)-2-hydroxy-3-((2-methylpropyl)((4-nitrophenyl)sulfonyl)amino)-1-(phenylmethyl)propyl)carbamate;(3S)-tetrahydro-3-furyl N-[(1S,2R)-1-benzyl-2-hydroxy-3-(N-isobutyl-4-nitrobenzene sulphonamido)propyl]carbamate;(S)-tetrahydrofuran-3-yl ((2S,3R)-3-hydroxy-4-((N-isobutyl-4-nitrophenyl)sulfonamido)-1-phenylbutan-2-yl)carbamate;[(1S,2R)-3-[[(4-Nitrophenyl)sulfonyl](2-methylpropyl)amino]-2-hydroxy-1-phenylmethyl)propyl]carbamic Acid, (3S)-Tetrahydro-3-furanyl Ester;[(1S,2R)-3-[[(4-Nitrophenyl)sulfonyl](2-methylpropyl)amino]-2-hydroxy-1-phenylmethyl)propyl]carbamic acid,(3S)-tetrahydro-3-furanyl ester;N-Isobutyl-N-[(2R,3S)-2-hydroxy-3-[[(3S)-3beta-oxolanyl]oxycarbonylamino]-4-phenylbutyl]-4-nitrobenzenesulfonamide

Chemical Property of [(1S,2R)-3-[[(4-Nitrophenyl)sulfonyl](2-methylpropyl)amino]-2-hydroxy-1-phenylmethyl)propyl]carbamic Acid, (3S)-Tetrahydro-3-furanyl Ester

Chemical Property:

• Melting Point: 161-162 °C
• PKA: 11.50±0.46(Predicted)
• PSA: 162.86000
• Density: 1.353g/cm³
• LogP: 4.53720
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 12
• Exact Mass: 535.19883619
• Heavy Atom Count: 37
• Complexity: 830

Purity/Quality:

98%,99%, ^*data from raw suppliers

[(1S,2R)-3-[[(4-Nitrophenyl)sulfonyl](2-methylpropyl)amino]-2-hydroxy-1-phenylmethyl)propyl]carbamicAcid,(3S)-Tetrahydro-3-furanylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CN(CC(C(CC1=CC=CC=C1)NC(=O)OC2CCOC2)O)S(=O)(=O)C3=CC=C(C=C3)[N+](=O)[O-]
• Isomeric SMILES: CC(C)CN(C[C@H]([C@H](CC1=CC=CC=C1)NC(=O)O[C@H]2CCOC2)O)S(=O)(=O)C3=CC=C(C=C3)[N+](=O)[O-]
• Uses: A intermediate in the synthesis of Amprenavir, a selective HIV protease inhibitor. An intermediate in the synthesis of Amprenavir, a selective HIV protease inhibitor.

Technology Process of [(1S,2R)-3-[[(4-Nitrophenyl)sulfonyl](2-methylpropyl)amino]-2-hydroxy-1-phenylmethyl)propyl]carbamic Acid, (3S)-Tetrahydro-3-furanyl Ester

There total 43 articles about [(1S,2R)-3-[[(4-Nitrophenyl)sulfonyl](2-methylpropyl)amino]-2-hydroxy-1-phenylmethyl)propyl]carbamic Acid, (3S)-Tetrahydro-3-furanyl Ester 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: 85.0%

1-({[(3S)-tetrahydro-3-furanyloxy]carbonyl}oxy)-2,5-pyrrolidinedione (138499-08-8) + [(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester (191226-98-9) → 4-nitro-N-((2R(syn),3S)-2-hydroxy-4-phenyl-3-((S)-tetrahydrofuran-3-yloxycarbonylamino)-butyl)-N-isobutylbenzenesulfonamide (160231-69-6)

Guidance literature:

[(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester; With hydrogenchloride; In dichloromethane; for 1.5h;

1-({[(3S)-tetrahydro-3-furanyloxy]carbonyl}oxy)-2,5-pyrrolidinedione; With triethylamine; In dichloromethane; at 20 ℃; for 4h; Further stages.;

DOI:10.1021/ol016147s

Reference yield: 80.0%

(S)-3-hydroxytetyrahydrofurane (86087-23-2,84921-89-1,864447-89-2) + 1,1'-carbonyldiimidazole (530-62-1) + N-(3S-amino-2R-hydroxy-4-phenylbutyl)-N-isobutyl-4-nitro-benzenesulfonamide hydrochloride (251105-80-3) → 4-nitro-N-((2R(syn),3S)-2-hydroxy-4-phenyl-3-((S)-tetrahydrofuran-3-yloxycarbonylamino)-butyl)-N-isobutylbenzenesulfonamide (160231-69-6)

Guidance literature:

In ethanol; ethyl acetate; for 17h; Heating;

DOI:10.1128/AAC.48.3.791-798.2004

Reference yield:

1-({[(3S)-tetrahydro-3-furanyloxy]carbonyl}oxy)-2,5-pyrrolidinedione (138499-08-8) + N-(3S-amino-2R-hydroxy-4-phenylbutyl)-N-isobutyl-4-nitro-benzenesulfonamide hydrochloride (251105-80-3) → 4-nitro-N-((2R(syn),3S)-2-hydroxy-4-phenyl-3-((S)-tetrahydrofuran-3-yloxycarbonylamino)-butyl)-N-isobutylbenzenesulfonamide (160231-69-6)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 4h;

upstream raw materials:

1-({[(3S)-tetrahydro-3-furanyloxy]carbonyl}oxy)-2,5-pyrrolidinedione

[(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester

(S)-3-hydroxytetyrahydrofurane

1,1'-carbonyldiimidazole

Downstream raw materials:

amprenavir