cas 160231-69-6, [(1S,2R)-3-[[(4-Nitrophenyl)sulfonyl](2-methylpropyl)amino]-2-hydroxy-1-phenylmethyl)propyl]carbamic Acid, (3S)-Tetrahydro-3-furanyl Ester

Articles about 160231-69-6Total 8 be found

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
Furfine, Eric S.,Baker, Christopher T.,Hale, Michael R.,Reynolds, David J.,Salisbury, Jo A.,Searle, Andy D.,Studenberg, Scott D.,Todd, Dan,Tung, Roger D.,Spaltenstein, Andrew
p. 791 - 798
(2004)
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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
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(2015/02/18)

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
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Paragraph 0051

(2013/07/19)

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).
Gadakh, Sunita K.,Santhosh Reddy,Sudalai, Arumugam
p. 898 - 903
(2012/09/22)

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
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Page/Page column 14

(2012/03/27)

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.
Honda, Yutaka,Katayama, Satoshi,Kojima, Mitsuhiko,Suzuki, Takayuki,Kishibata, Naomi,Izawa, Kunisuke
p. 2061 - 2070
(2007/10/03)

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.
Kazmierski, Wieslaw M.,Bevans, Patricia,Furfine, Eric,Spaltenstein, Andrew,Yang, Hanbiao
p. 2523 - 2526
(2007/10/03)

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.
Kim,Bae,So,Yoo,Chang,Lee,Kang
p. 2349 - 2351
(2007/10/03)