Benzenesulfonamide,N-[(2R,3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-(2-methylpropyl)-4-nitro-

Base Information

• Chemical Name: Benzenesulfonamide,N-[(2R,3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-(2-methylpropyl)-4-nitro-
• CAS No.: 251105-80-3
• Molecular Formula: C20H27N3O5S
• Molecular Weight: 421.517
• UNII: ZCS43QNB97
• Nikkaji Number: J3.620.613F
• Wikidata: Q76415143
• Mol file: 251105-80-3.mol

Synonyms:251105-80-3;ZCS43QNB97;Benzenesulfonamide,N-[(2R,3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-(2-methylpropyl)-4-nitro-;N-((2R,3S)-3-amino-2-hydroxy-4-phenylbutyl)-N-isobutyl-4-nitrobenzenesulfonamide;Benzenesulfonamide, N-((2R,3S)-3-amino-2-hydroxy-4-phenylbutyl)-N-(2-methylpropyl)-4-nitro-;N-((2R,3S)-3-Amino-2-hydroxy-4-phenylbutyl)-N-(2-methylpropyl)-4-nitrobenzenesulfonamide;UNII-ZCS43QNB97;SCHEMBL469706;AC-32463;J3.620.613F;J-519684;N-(2-Methylpropyl)-N-[(2R,3S)-2-hydroxy-3-amino-4-phenylbutyl]-4-nitrobenzenesulfonamide

Chemical Property of Benzenesulfonamide,N-[(2R,3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-(2-methylpropyl)-4-nitro-

Chemical Property:

• XLogP3: 2.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 9
• Exact Mass: 421.16714214
• Heavy Atom Count: 29
• Complexity: 603

Purity/Quality:

99% ^*data from raw 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)N)O)S(=O)(=O)C2=CC=C(C=C2)[N+](=O)[O-]
• Isomeric SMILES: CC(C)CN(C[C@H]([C@H](CC1=CC=CC=C1)N)O)S(=O)(=O)C2=CC=C(C=C2)[N+](=O)[O-]

Technology Process of Benzenesulfonamide,N-[(2R,3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-(2-methylpropyl)-4-nitro-

There total 23 articles about Benzenesulfonamide,N-[(2R,3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-(2-methylpropyl)-4-nitro- 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%

[(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester (191226-98-9) → N-(3S-amino-2R-hydroxy-4-phenylbutyl)-N-isobutyl-4-nitro-benzenesulfonamide hydrochloride (251105-80-3)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 0 - 20 ℃; for 3h;

DOI:10.1002/ejoc.201600062

Reference yield: 70.0%

isobutylamine (78-81-9) + (1-oxiranyl-2-phenylethyl)carbamic acid tert-butyl ester (98760-08-8,98818-34-9,98818-35-0,103127-56-6,98737-29-2) + 4-Nitrobenzenesulfonyl chloride (98-74-8) → N-(3S-amino-2R-hydroxy-4-phenylbutyl)-N-isobutyl-4-nitro-benzenesulfonamide hydrochloride (251105-80-3)

Guidance literature:

isobutylamine; (1-oxiranyl-2-phenylethyl)carbamic acid tert-butyl ester; In toluene; for 2.5h; Heating;

4-Nitrobenzenesulfonyl chloride; With triethylamine; In toluene; Heating;

With hydrogenchloride; In toluene; for 1.5h; Heating;

DOI:10.1128/AAC.48.3.791-798.2004

Reference yield:

(2R,3S)-N-isobutyl-N-(2-hydroxy-3-azido-4-phenylbutyl)-p-nitrobenzenesulfonylamide → N-(3S-amino-2R-hydroxy-4-phenylbutyl)-N-isobutyl-4-nitro-benzenesulfonamide hydrochloride (251105-80-3)

Guidance literature:

(2R,3S)-N-isobutyl-N-(2-hydroxy-3-azido-4-phenylbutyl)-p-nitrobenzenesulfonylamide; With triphenylphosphine; In tetrahydrofuran; at 25 ℃; for 0.5h;

With water; In tetrahydrofuran; for 29h;

DOI:10.1016/j.tetasy.2012.06.003

upstream raw materials:

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

4-nitro-N-((2R(syn),3S)-3-(N-benzyloxycarbonylamino)-2-hydroxy-4-phenylbutyl)-N-isobutyl-benzenesulfonamide

isobutylamine

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

Downstream raw materials:

2-oxo-3-phenyl-oxazolidine-5-carboxylic acid {1-benzyl-2-hydroxy-3-[isobutyl-(4-nitro-benzenesulfonyl)-amino]-propyl}-amide

2-oxo-3-phenyl-oxazolidine-5-carboxylic acid {1-benzyl-2-hydroxy-3-[isobutyl-(4-nitro-benzenesulfonyl)-amino]-propyl}-amide

3-(3-fluoro-phenyl)-2-oxo-oxazolidine-5-carboxylic acid {1-benzyl-2-hydroxy-3-[isobutyl-(4-nitro-benzenesulfonyl)-amino]-propyl}-amide

3-(4-acetyl-phenyl)-2-oxo-oxazolidine-5-carboxylic acid {1-benzyl-2-hydroxy-3-[isobutyl-(4-nitro-benzenesulfonyl)-amino]-propyl}-amide

Refernces

• 1、 Zhu, Mei,Shan, Qi,Ma, Ling,Wen, Jiajia,Dong, Biao,Zhang, Guoning,Wang, Minghua,Wang, Juxian,Zhou, Jinming,Cen, Shan,Wang, Yucheng. "Design and biological evaluation of cinnamic and phenylpropionic amide derivatives as novel dual inhibitors of HIV-1 protease and reverse transcriptase". . . Retrieved 2021/05/04.
• 2、 Zhu, Mei,Ma, Ling,Wen, Jiajia,Dong, Biao,Wang, Yujia,Wang, Zhen,Zhou, Jinming,Zhang, Guoning,Wang, Juxian,Guo, Ying,Liang, Chen,Cen, Shan,Wang, Yucheng. "Rational design and Structure?Activity relationship of coumarin derivatives effective on HIV-1 protease and partially on HIV-1 reverse transcriptase". . . Retrieved 2019/12/09.