162849-95-8

Basic information

• Product Name: (2S,3S,5S)-5-(tert-Butoxycarbonylamino)-2-(N-5-thiazolylmethoxycarbonyl)amino-1,6-diphenyl-3-hydroxyhexane
• Synonyms: (2S,3S,5S)-5-(tert-Butoxycarbonylamino)-2-(N-5-thiazolylmethoxycarbonyl)amino-1,6-diphenyl-3-hydroxyhexane;tert-Butyl (thiazol-5-ylmethyl) ((2S,3S,5S)-3-hydroxy-1,6-diphenylhexane-2,5-diyl)dicarbamate;N-[(1S,2S,4S)-4-[[(1,1-DiMethylethoxy)carbonyl]aMino]-2-hydroxy-5-phenyl-1-(phenylMethyl)pentyl]carbaMic Acid 5-ThiazolylMethyl Ester
• CAS NO: 162849-95-8
• Molecular Formula: C₂₈H₃₅N₃O₅S
• Molecular Weight: 526
• Mol File: 162849-95-8.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 722.3±60.0 °C(Predicted)
• Appearance: /
• Density: 1.219
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 11.48±0.46(Predicted)
• CAS DataBase Reference: (2S,3S,5S)-5-(tert-Butoxycarbonylamino)-2-(N-5-thiazolylmethoxycarbonyl)amino-1,6-diphenyl-3-hydroxyhexane(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3S,5S)-5-(tert-Butoxycarbonylamino)-2-(N-5-thiazolylmethoxycarbonyl)amino-1,6-diphenyl-3-hydroxyhexane(162849-95-8)
• EPA Substance Registry System: (2S,3S,5S)-5-(tert-Butoxycarbonylamino)-2-(N-5-thiazolylmethoxycarbonyl)amino-1,6-diphenyl-3-hydroxyhexane(162849-95-8)

Safety Data

• Hazardous Substances Data: 162849-95-8(Hazardous Substances Data)

Usage

Uses

N-[(1S,2S,4S)-4-[[(1,1-Dimethylethoxy)carbonyl]amino]-2-hydroxy-5-phenyl-1-(phenylmethyl)pentyl]carbamic Acid 5-Thiazolylmethyl Ester (Ritonavir EP Impurity J) is an intermediate in the synthesis of Ritonavir (R535000), a selective HIV protease inhibitor used for the treatment of HIV infections and AIDS.

Upstream product

• 144163-97-3 ((5-thiazolyl)methyl)-(4-nitrophenyl)carbonate 
• 256328-84-4 (2S,3S,5S)-2-amino-3-hydroxy-5-tert-butoxycarbonylamino-1,6-diphenylhexane succinate 
• 154212-59-6 5-(p-nitrophenyloxycarbonyloxymethyl)thiazole hydrochloride 
• 144163-85-9 (2S,3S,5S)-2-amino-3-hydroxy-5-(t-butyloxycarbonylamino)-1,6-diphenylhexane 

Downstream Products

• 566939-06-8 (2S,3S,5S)-3-[O-[N-[N-methyl-N-[(2-isopropyl-4-thiazolyl)methyl]amino]carbonyl]-L-valyloxy]-5-[N-[(tert-butyloxy)carbonyl]amino]-2-[N-[(5-thiazolyl)methoxycarbonyl]amino]-1,6-diphenyl-3-hydroxyhexane 
• 144164-11-4 (2S,3S,5S)-5-Amino-2-(N-((5-thiazolyl)-methoxycarbonyl)amino)-3-hydroxy-1,6-diphenylhexane 
• 155213-67-5 ritonavir 
• 1448312-70-6 1,6-diphenyl-5(S)-tert-butoxycarbonylamino-2(S)-(5-thiazolemethoxy)carbonylamino-hexane 
• 1448312-69-3 3(S)-imidazolecarbothioic acid 1,6-diphenyl-5(S)-tert-butoxycarbonylamino-2(S)-(5-thiazolemethoxycarbonylamino)hexane, ester 

Relevant articles and documents

Design and synthesis of selenazole-substituted ritonavir analogs

With the help of Surflex-Dock calculation, two ritonavir analogs in which one thioazole unit was replaced by selenazole have been designed and synthesized. The key selenazole structure was constructed from β-azido diselenide through a cascade diselenide cleavage/selenocarbonylation/Staudinger reduction/aza-Wittig reaction and a following MnO2 oxidation. The accordingly prepared compounds exhibited good anti-HIV-1 (IIIB) activities comparable to that of the original ritonavir, as well as the positive SI values.

METHODS AND INTERMEDIATES FOR PREPARING PHARMACEUTICAL AGENTS

Methods and intermediates useful for preparing a compound of formula I and salts thereof.

A PROCESS FOR THE SYNTHESIS OF 2-AMINO-5-PROTECTED AMINO-3-HYDROXY-1, 6-DIPHENYLHEXANE OR A SALT THEREOF - AN INTERMEDIATE FOR ANTIVIRAL DRUGS

The present invention relates to an improved process for preparing 2-amino-5-protected-amino-3-hydroxy-1,6-diphenylhexane compounds or acid addition salts thereof, which can be useful intermediates for preparing compounds with antiviral activity. The present invention further provides a process for preparing HIV protease inhibitors, lopinavir and ritonavir.