160231-69-6

Usage

Uses

Used in Pharmaceutical Industry:
[(1S,2R)-3-[[(4-Nitrophenyl)sulfonyl](2-methylpropyl)amino]-2-hydroxy-1-phenylmethyl)propyl]carbamic Acid, (3S)-Tetrahydro-3-furanyl Ester is used as an intermediate in the synthesis of Amprenavir for its role in inhibiting the replication of the HIV virus. This application is significant in the development of treatments for HIV and AIDS, contributing to the fight against these life-threatening diseases.

InChI:InChI=1/C25H33N3O8S/c1-18(2)15-27(37(33,34)22-10-8-20(9-11-22)28(31)32)16-24(29)23(14-19-6-4-3-5-7-19)26-25(30)36-21-12-13-35-17-21/h3-11,18,21,23-24,29H,12-17H2,1-2H3,(H,26,30)/t21-,23-,24+/m0/s1

Upstream product

• 178153-11-2 (S)-tetrahydrofuran-3-yl carbonochloridate 
• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 
• 326479-99-6 2(R)-((tert-butyloxycarbonyl)amino)-1,4-dichloro-3(S)-hydroxybutane 
• 206361-96-8 (2R,3R)-3-azido-4-phenylbutane-1,2-diol 
• 98-74-8 4-Nitrobenzenesulfonyl chloride 
• 136465-89-9 (2S)-2-[1'(S)-1-azido-2-phenylethyl]oxirane 
• 78571-81-0 (3-benzyloxiran-2-yl)methanol 
• 42238-15-3 (2E)-4-phenylbut-2-en-1-ol 
• 54966-42-6 ethyl 3-benzylacrylate 
• 138499-08-8 1-({[(3S)-tetrahydro-3-furanyloxy]carbonyl}oxy)-2,5-pyrrolidinedione 
• 251105-80-3 N-(3S-amino-2R-hydroxy-4-phenylbutyl)-N-isobutyl-4-nitro-benzenesulfonamide hydrochloride 
• 326480-02-8 2(S)-t-butyldimethylsilyloxy-3(S)-(t-butyloxycarbonyl)amino-1-chloro-4-phenylbutane 
• 357604-38-7 [(1S,2S)-1-Benzyl-3-chloro-2-(tetrahydro-pyran-2-yloxy)-propyl]-carbamic acid tert-butyl ester 
• 357604-36-5 [(1R,2S)-3-Chloro-1-chloromethyl-2-(tetrahydro-pyran-2-yloxy)-propyl]-carbamic acid tert-butyl ester 

Downstream Products

• 161814-49-9 amprenavir 

Relevant academic research and scientific papers

Preclinical Pharmacology and Pharmacokinetics of GW433908, a Water-Soluble Prodrug of the Human Immunodeficiency Virus Protease Inhibitor Amprenavir

GW433908 is the water-soluble, phosphate ester prodrug of the human immunodeficiency virus type 1 protease inhibitor amprenavir (APV). A high-yield synthesis of GW433908 is achieved by phosphorylation of the penultimate precursor of APV with phosphorous o

PROCESS FOR SYNTHESIS OF SYN AZIDO EPOXIDE AND ITS USE AS INTERMEDIATE FOR THE SYNTHESIS OF AMPRENAVIR and SAQUINAVIR

Disclosed herein is a novel route of synthesis of syn azide epoxide of formula 5, which is used as a common intermediate for asymmetric synthesis of HIV protease inhibitors such as Amprenavir, Fosamprenavir, Saquinavir and formal synthesis of Darunavir an

PROCESS FOR PREPARATION OF SUBSTANTIALLY PURE FOSAMPRENAVIR CALCIUM AND ITS INTERMEDIATES

The present invention relates to fosamprenavir calcium (Ia) substantially free of isomer impurity, (3R) tetrahydro -3 -furanyl(1S,2R)-3-[[(4-aminophenyl)sulfonyl](isobutyl)amino]-1-benzyl-2-(phosphonooxy)propyl carbamate (Ib), and its process for preparat

Enantioselective synthesis of HIV protease inhibitor amprenavir via Co-catalyzed HKR of 2-(1-azido-2-phenylethyl)oxirane

A short and efficient enantioselective synthesis of the HIV protease inhibitor amprenavir 1 (99% ee) as well as a formal synthesis of saquinavir 3 have been achieved in high enantiomeric purity starting from commercially available materials. Our strategy mainly comprises a Co-catalyzed two-stereocentred hydrolytic kinetic resolution (HKR) of racemic 2-(1-azido-2-phenylethyl)oxirane as the chirality inducing step. Also presented is a concise synthesis of (S)-3-hydroxytetrahydrofuran 4, the key structural feature, in high enantiomeric purity (98% ee).

PROCESS FOR PREPARATION OF SUBSTANTIALLY PURE FOSAMPRENAVIR CALCIUM AND ITS INTERMEDIATES

The present invention relates to fosamprenavir calcium (la) substantially free of isomer impurity, (3R) tetrahydro-3-furanyl(1S,2R)-3-[[(4-aminophenyl) sulfonyl] (isobutyl) amino]- 1-benzyl-2-(phosphonooxy)propyl carbamate (lb), and its process for prepar

New approaches to the industrial synthesis of HIV protease inhibitors

Efficient and industrially applicable synthetic processes for precursors of HIV protease inhibitors (Amprenavir, Fosamprenavir) are described. These involve a novel and economical method for the preparation of a key intermediate, (3S)-hydroxytetrahydrofuran, from L-malic acid. Three new approaches to the assembly of Amprenavir are also discussed. Of these, a synthetic route in which an (S)-tetrahydrofuranyloxy carbonyl is attached to L-phenylalanine appears to be the most promising manufacturing process, in that it offers satisfactory stereoselectivity in fewer steps.

Novel prodrug approach to amprenavir-based HIV-1 protease inhibitors via O→N acyloxy migration of P1 moiety

We have developed a new approach to prodrugs, which utilizes a pH-induced intramolecular O→N migration of an acyloxy group in carbonate moiety to a free amino moiety at neutral pH. This method is exemplified by facile rearrangement of highly water-soluble prodrug 3 to carbamate 4, a close analogue of HIV-1 protease inhibitor Amprenavir. The O→N acyloxy migration is unprecedented in the context of prodrugs and it enables a high atom economy due to recycling of the 'pro' moiety.

Synthesis of a chiral aziridine derivative as a versatile intermediate for HIV protease inhibitors.

[reaction: see text] Chiral aziridine derivative 1 was prepared from D-tartaric acid. This compound could be utilized as a common intermediate for the synthesis of hydroxyethylamine class HIV protease inhibitors such as saquinavir, amprenavir, or nelfinavir.