[(3aS,4R,6aR)-2,3,3a,4,5,6a-hexahydrofuro[2,3-b]furan-4-yl] N-[(2S,3R)-3-hydroxy-4-[2-methylpropyl-(4-nitrophenyl)sulfonylamino]-1-phenylbutan-2-yl]carbamate

Base Information

• Chemical Name: [(3aS,4R,6aR)-2,3,3a,4,5,6a-hexahydrofuro[2,3-b]furan-4-yl] N-[(2S,3R)-3-hydroxy-4-[2-methylpropyl-(4-nitrophenyl)sulfonylamino]-1-phenylbutan-2-yl]carbamate
• CAS No.: 799241-76-2
• Molecular Formula: C₂₇H₃₅N₃O₉S
• Molecular Weight: 577.656
• UNII: QM3AMB3LV5
• ChEMBL ID: CHEMBL175861
• Mol file: 799241-76-2.mol

Synonyms:Darunavir impurity 23;QM3AMB3LV5;799241-76-2;[(3aS,4R,6aR)-2,3,3a,4,5,6a-hexahydrofuro[2,3-b]furan-4-yl] N-[(2S,3R)-3-hydroxy-4-[2-methylpropyl-(4-nitrophenyl)sulfonylamino]-1-phenylbutan-2-yl]carbamate;(3R,3aS,6aR)-Hexahydrofuro(2,3-b)furan-3-yl ((2S,3R)-3-hydroxy-4-((N-isobutyl-4-nitrophenyl)sulfonamido)-1-phenylbutan-2-yl)carbamate;(3R,3aS,6aR)-Hexahydrofuro(2,3-b)furan-3-yl ((2S,3R)-3-hydroxy-4-(N-isobutyl-4-nitrophenylsulfonamido)-1-phenylbutan-2-yl)carbamate;(3R,3aS,6aR)-Hexahydrofuro(2,3-b)furan-3-yl N-((1S,2R)-2-hydroxy-3-((2-methylpropyl)((4-nitrophenyl)sulfonyl)amino)-1-(phenylmethyl)propyl)carbamate;Carbamic acid, N-((1S,2R)-2-hydroxy-3-((2-methylpropyl)((4-nitrophenyl)sulfonyl)amino)-1-(phenylmethyl)propyl)-, (3R,3aS,6aR)-hexahydrofuro(2,3-b)furan-3-yl ester;UNII-QM3AMB3LV5;CHEMBL175861;SCHEMBL1898455;YCZAREAHOZXNLL-HEXNFIEUSA-N;[(3aS,4R,6aR)-2,3,3a,4,5,6a-hexahydrofuro[2,3-b]furan-4-yl] N-[(1S,2R)-1-benzyl-2-hydroxy-3-[isobutyl-(4-nitrophenyl)sulfonyl-amino]propyl]carbamate;Carbamic acid, [(1S,2R)-2-hydroxy-3-[[(4-nitrophenyl)sulfonyl](2-methylpropyl)amino]-1-(phenylmethyl)propyl]-, (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl ester

Chemical Property of [(3aS,4R,6aR)-2,3,3a,4,5,6a-hexahydrofuro[2,3-b]furan-4-yl] N-[(2S,3R)-3-hydroxy-4-[2-methylpropyl-(4-nitrophenyl)sulfonylamino]-1-phenylbutan-2-yl]carbamate

Chemical Property:

• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform, Methanol
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 12
• Exact Mass: 577.20940088
• Heavy Atom Count: 40
• Complexity: 940

Purity/Quality:

99.9% ^*data from raw suppliers

N-[(1S,2R)-2-Hydroxy-3-[(2-methylpropyl)[(4-nitrophenyl)sulfonyl]amino]-1-(phenylmethyl)propyl]carbamicAcid(3R,3aS,6aR)-Hexahydrofuro[2,3-b]furan-3-ylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)CN(CC(C(CC1=CC=CC=C1)NC(=O)OC2COC3C2CCO3)O)S(=O)(=O)C4=CC=C(C=C4)[N+](=O)[O-]
• Isomeric SMILES: CC(C)CN(C[C@H]([C@H](CC1=CC=CC=C1)NC(=O)O[C@H]2CO[C@@H]3[C@H]2CCO3)O)S(=O)(=O)C4=CC=C(C=C4)[N+](=O)[O-]
• Uses: N-[(1S,2R)-2-hydroxy-3-[(2-methylpropyl)[(4-nitrophenyl)sulfonyl]amino]-1-(phenylmethyl)propyl]carbamic Acid (3R,3aS,6aR)-Hexahydrofuro[2,3-b]furan-3-yl Ester is an intermediate in the synthesis of 1-epi-Darvunavir (D193505), a second generation HIV-1-protease inhibitor.

Technology Process of [(3aS,4R,6aR)-2,3,3a,4,5,6a-hexahydrofuro[2,3-b]furan-4-yl] N-[(2S,3R)-3-hydroxy-4-[2-methylpropyl-(4-nitrophenyl)sulfonylamino]-1-phenylbutan-2-yl]carbamate

There total 13 articles about [(3aS,4R,6aR)-2,3,3a,4,5,6a-hexahydrofuro[2,3-b]furan-4-yl] N-[(2S,3R)-3-hydroxy-4-[2-methylpropyl-(4-nitrophenyl)sulfonylamino]-1-phenylbutan-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: 99.1%

C15H13NO7 + N-(3S-amino-2R-hydroxy-4-phenylbutyl)-N-isobutyl-4-nitro-benzenesulfonamide hydrochloride (251105-80-3) → (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl N-{(1S,2R)-2-hydroxy-3-[(2-methylpropyl)-4-nitrophenylsulfonylamino]-1-phenylmethylpropyl}carbamate (799241-76-2)

Guidance literature:

In tetrahydrofuran; at 30 ℃; for 6h;

Reference yield: 98.9%

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione (253265-97-3) + N-(3S-amino-2R-hydroxy-4-phenylbutyl)-N-isobutyl-4-nitro-benzenesulfonamide hydrochloride (251105-80-3) → (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl N-{(1S,2R)-2-hydroxy-3-[(2-methylpropyl)-4-nitrophenylsulfonylamino]-1-phenylmethylpropyl}carbamate (799241-76-2)

Guidance literature:

In tetrahydrofuran; at 30 ℃; for 6h;

Reference yield: 87.5%

C7H9ClO4 + N-(3S-amino-2R-hydroxy-4-phenylbutyl)-N-isobutyl-4-nitro-benzenesulfonamide hydrochloride (251105-80-3) → (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl N-{(1S,2R)-2-hydroxy-3-[(2-methylpropyl)-4-nitrophenylsulfonylamino]-1-phenylmethylpropyl}carbamate (799241-76-2)

Guidance literature:

In dichloromethane; at 45 ℃; for 10h;

upstream raw materials:

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

N-(3S-amino-2R-hydroxy-4-phenylbutyl)-N-isobutyl-4-nitro-benzenesulfonamide hydrochloride

(1-oxiranyl-2-phenylethyl)carbamic acid tert-butyl ester

(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol

Refernces

• 1、 Kanemitsu, Takuya,Inoue, Mizuho,Yoshimura, Nono,Yoneyama, Kazutoshi,Watarai, Rie,Miyazaki, Michiko,Odanaka, Yuki,Nagata, Kazuhiro,Itoh, Takashi. "A Concise One-Pot Organo- and Biocatalyzed Preparation of Enantiopure Hexahydrofuro[2,3-b]furan-3-ol: An Approach to the Synthesis of HIV Protease Inhibitors". . p. 1874 - 1880. Retrieved 2016/05/09.
• 2、 Surleraux, Dominique L. N. G.,Tahri, Abdellah,Verschueren, Wim G.,Pille, Geert M. E.,De Kock, Herman A.,Jonckers, Tim H. M.,Peeters, Anik,De Meyer, Sandra,Azijn, Hilde,Pauwels, Rudi,De Bethune, Marie-Pierre,King, Nancy M.,Prabu-Jeyabalan, Moses,Schiffer, Celia A.,Wigerinck, Piet B. T. P.. "Discovery and selection of TMC114, a next generation HIV-1 protease inhibitor". . p. 1813 - 1822. Retrieved 2007/10/03.