e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

Studies toward the large-scale synthesis of the HIV proteinase inhibitor Ro 31-8959

KEB Parkes, DJ Bushnell, PH Crackett…

Index: Journal of Organic Chemistry, , vol. 59, # 13 p. 3656 - 3664

Full Text: HTML

Citation Number: 124

Abstract

... (14) Maibaum, J.; Rich, DH J . Org. Chem. ... The tris- ((trimethylsily1)oxy)ethene chemistry developed by Wiss- ner for the preparation of a-hydroxymethyl ketones from acid chlorides offered a potentially attractive method of preparing a homophenylalanine synthon of the sort ...

(2S,3S)-2-azido-1-phenyl-butane-3,4-diol Structure

(2S,3S)-2-azido...

~%

(3S,4aS,8aS)-2-[(3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-tert-butyl-3,4,4a,5,6,7,8,8a-octahydro-1H-isoquinoline-3-carboxamide Structure

(3S,4aS,8aS)-2-...

N-Cbz-L-Phenylalanine Structure

N-Cbz-L-Phenyla...

~%

(3S,4aS,8aS)-2-[(3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-tert-butyl-3,4,4a,5,6,7,8,8a-octahydro-1H-isoquinoline-3-carboxamide Structure

(3S,4aS,8aS)-2-...

N/A Structure

~%

(3S,4aS,8aS)-2-[(3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-tert-butyl-3,4,4a,5,6,7,8,8a-octahydro-1H-isoquinoline-3-carboxamide Structure

(3S,4aS,8aS)-2-...

4(S)-(1(S)-Azido-2-phenylethyl)-1,3,2-dioxathiolane 2,2-dioxide Structure

4(S)-(1(S)-Azid...

~%

(3S,4aS,8aS)-2-[(3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-tert-butyl-3,4,4a,5,6,7,8,8a-octahydro-1H-isoquinoline-3-carboxamide Structure

(3S,4aS,8aS)-2-...

3(S)-(Benzyloxyformamido)-1-bromo-4-phenyl-2(S)-butanol Structure

3(S)-(Benzyloxy...

~%

(3S,4aS,8aS)-2-[(3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-tert-butyl-3,4,4a,5,6,7,8,8a-octahydro-1H-isoquinoline-3-carboxamide Structure

(3S,4aS,8aS)-2-...

ethyl (S)-4-benzyloxycarbonylamino-3-oxo-5-phenylpentanoate Structure

ethyl (S)-4-ben...

~%

(3S,4aS,8aS)-2-[(3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-tert-butyl-3,4,4a,5,6,7,8,8a-octahydro-1H-isoquinoline-3-carboxamide Structure

(3S,4aS,8aS)-2-...

4(S)-Benzyl-3-(benzyloxycarbonyl)-2,2-dimethyl-5(R)-oxazolidineacetic acid Structure

4(S)-Benzyl-3-(...

~%

(3S,4aS,8aS)-2-[(3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-tert-butyl-3,4,4a,5,6,7,8,8a-octahydro-1H-isoquinoline-3-carboxamide Structure

(3S,4aS,8aS)-2-...

N/A Structure

~%

(3S,4aS,8aS)-2-[(3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-tert-butyl-3,4,4a,5,6,7,8,8a-octahydro-1H-isoquinoline-3-carboxamide Structure

(3S,4aS,8aS)-2-...

Ethyl 4(S)-benzyl-3-(benzyloxycarbonyl)-2,2-dimethyl-5(R)-oxazolidineacetate Structure

Ethyl 4(S)-benz...

~%

(3S,4aS,8aS)-2-[(3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-tert-butyl-3,4,4a,5,6,7,8,8a-octahydro-1H-isoquinoline-3-carboxamide Structure

(3S,4aS,8aS)-2-...

N/A Structure

~%

(3S,4aS,8aS)-2-[(3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-tert-butyl-3,4,4a,5,6,7,8,8a-octahydro-1H-isoquinoline-3-carboxamide Structure

(3S,4aS,8aS)-2-...

Boc-L-phenylalanine Structure

Boc-L-phenylalanine

~%

(3S,4aS,8aS)-2-[(3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-tert-butyl-3,4,4a,5,6,7,8,8a-octahydro-1H-isoquinoline-3-carboxamide Structure

(3S,4aS,8aS)-2-...

N-Boc-L-phenylalaninal Structure

N-Boc-L-phenyla...

~%

(3S,4aS,8aS)-2-[(3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-tert-butyl-3,4,4a,5,6,7,8,8a-octahydro-1H-isoquinoline-3-carboxamide Structure

(3S,4aS,8aS)-2-...

2-(2(S)-(tert-Butoxyformamido)-1-hydroxy-3-phenylpropyl)thiazole Structure

2-(2(S)-(tert-B...

~%

(3S,4aS,8aS)-2-[(3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-tert-butyl-3,4,4a,5,6,7,8,8a-octahydro-1H-isoquinoline-3-carboxamide Structure

(3S,4aS,8aS)-2-...

(S,S)-2-(2-(N-(tert-Butoxycarbonyl)amino)-1-hydroxy-3-phenylpropyl)-1,3-thiazole Structure

(S,S)-2-(2-(N-(...

~%

(3S,4aS,8aS)-2-[(3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-tert-butyl-3,4,4a,5,6,7,8,8a-octahydro-1H-isoquinoline-3-carboxamide Structure

(3S,4aS,8aS)-2-...

N-Boc-β-keto-γ-phenylalanine Structure

N-Boc-β-keto-γ-...

~%

(3S,4aS,8aS)-2-[(3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-tert-butyl-3,4,4a,5,6,7,8,8a-octahydro-1H-isoquinoline-3-carboxamide Structure

(3S,4aS,8aS)-2-...

Boc-gF(b-OH)-OEt Structure

Boc-gF(b-OH)-OEt

~%

(3S,4aS,8aS)-2-[(3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-tert-butyl-3,4,4a,5,6,7,8,8a-octahydro-1H-isoquinoline-3-carboxamide Structure

(3S,4aS,8aS)-2-...

(2S,3S)-1-bromo-3-((tert-butoxycarbonyl)amino)-4-phenyl-2-butanol Structure

(2S,3S)-1-bromo...

~%

(3S,4aS,8aS)-2-[(3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-tert-butyl-3,4,4a,5,6,7,8,8a-octahydro-1H-isoquinoline-3-carboxamide Structure

(3S,4aS,8aS)-2-...

(4S,5S)-4-benzyl-5-(bromomethyl)-3-(tert-butoxycarbonyl)-2,2-dimethyloxazolidine Structure

(4S,5S)-4-benzy...

~%

(3S,4aS,8aS)-2-[(3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-tert-butyl-3,4,4a,5,6,7,8,8a-octahydro-1H-isoquinoline-3-carboxamide Structure

(3S,4aS,8aS)-2-...

3(S)-(tert-Butoxyformamido)-2(S)-hydroxy-4-phenyl-1-butanal Structure

3(S)-(tert-Buto...

~%

(3S,4aS,8aS)-2-[(3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-tert-butyl-3,4,4a,5,6,7,8,8a-octahydro-1H-isoquinoline-3-carboxamide Structure

(3S,4aS,8aS)-2-...

4(S)-Benzyl-3-(tert-butoxycarbonyl)-2,2-dimethyl-5(R)-oxazolidineacetic acid chloride Structure

4(S)-Benzyl-3-(...

~%

(3S,4aS,8aS)-2-[(3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-tert-butyl-3,4,4a,5,6,7,8,8a-octahydro-1H-isoquinoline-3-carboxamide Structure

(3S,4aS,8aS)-2-...

4(S)-Benzyl-3-(tert-butoxycarbonyl)-2,2-dimethyl-5(R)-oxazolidineacetic acid Structure

4(S)-Benzyl-3-(...

~%

(3S,4aS,8aS)-2-[(3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-tert-butyl-3,4,4a,5,6,7,8,8a-octahydro-1H-isoquinoline-3-carboxamide Structure

(3S,4aS,8aS)-2-...

Ethyl 4(S)-benzyl-3-(tert-butoxycarbonyl)-2,2-dimethyl-5(R)-oxazolidineacetate Structure

Ethyl 4(S)-benz...

~%

(3S,4aS,8aS)-2-[(3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-tert-butyl-3,4,4a,5,6,7,8,8a-octahydro-1H-isoquinoline-3-carboxamide Structure

(3S,4aS,8aS)-2-...

2(R)-(Methanesulfonyloxy)-4-phenyl-3(S)-phthalimido-1-butanol Structure

2(R)-(Methanesu...

~%

(3S,4aS,8aS)-2-[(3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-tert-butyl-3,4,4a,5,6,7,8,8a-octahydro-1H-isoquinoline-3-carboxamide Structure

(3S,4aS,8aS)-2-...

N/A Structure

~%

(3S,4aS,8aS)-2-[(3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-tert-butyl-3,4,4a,5,6,7,8,8a-octahydro-1H-isoquinoline-3-carboxamide Structure

(3S,4aS,8aS)-2-...

N/A Structure

~%

(3S,4aS,8aS)-2-[(3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-tert-butyl-3,4,4a,5,6,7,8,8a-octahydro-1H-isoquinoline-3-carboxamide Structure

(3S,4aS,8aS)-2-...

N/A Structure

~%

(3S,4aS,8aS)-2-[(3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-tert-butyl-3,4,4a,5,6,7,8,8a-octahydro-1H-isoquinoline-3-carboxamide Structure

(3S,4aS,8aS)-2-...

(1S,2S)-2-((tert-butoxycarbonyl)amino)-3-phenyl-1-(thiazol-2-yl)propyl acetate Structure

(1S,2S)-2-((ter...

~%

(3S,4aS,8aS)-2-[(3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-tert-butyl-3,4,4a,5,6,7,8,8a-octahydro-1H-isoquinoline-3-carboxamide Structure

(3S,4aS,8aS)-2-...

N-tert-Butyldecahydro-2-(2(R)-hydroxy-4-phenyl-3(S)phthalimidobutyl)-(4aS,8aS)-isoquinoline-3(S)-carboxamide Structure

N-tert-Butyldec...

~%

(3S,4aS,8aS)-2-[(3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-tert-butyl-3,4,4a,5,6,7,8,8a-octahydro-1H-isoquinoline-3-carboxamide Structure

(3S,4aS,8aS)-2-...

N-Cbz-L-Phenylalanine Structure

N-Cbz-L-Phenyla...

~%

Saquinavir Structure

2-(2(S)-(tert-Butoxyformamido)-1-hydroxy-3-phenylpropyl)thiazole Structure

2-(2(S)-(tert-B...

~%

Saquinavir Structure

(S,S)-2-(2-(N-(tert-Butoxycarbonyl)amino)-1-hydroxy-3-phenylpropyl)-1,3-thiazole Structure

(S,S)-2-(2-(N-(...

~%

Saquinavir Structure

N-Boc-β-keto-γ-phenylalanine Structure

N-Boc-β-keto-γ-...

~%

Saquinavir Structure

(2R,3S)-3-(tert-Butoxycarbonyl)aMino-1,2-epoxy-4-phenylbutane Structure

(2R,3S)-3-(tert...

~%

Saquinavir Structure

Boc-gF(b-OH)-OEt Structure

Boc-gF(b-OH)-OEt

~%

Saquinavir Structure

(2S,3S)-1-bromo-3-((tert-butoxycarbonyl)amino)-4-phenyl-2-butanol Structure

(2S,3S)-1-bromo...

~%

Saquinavir Structure

(4S,5S)-4-benzyl-5-(bromomethyl)-3-(tert-butoxycarbonyl)-2,2-dimethyloxazolidine Structure

(4S,5S)-4-benzy...

~%

Saquinavir Structure

(2S,3S)-2-azido-1-phenyl-butane-3,4-diol Structure

(2S,3S)-2-azido...

~%

Saquinavir Structure

tert-butyl N-[(2S,3R)-4-[(3S,4aS,8aS)-3-(tert-butylcarbamoyl)-3,4,4a,5,6,7,8,8a-octahydro-1H-isoquinolin-2-yl]-3-hydroxy-1-phenylbutan-2-yl]carbamate Structure

tert-butyl N-[(...

~%

Saquinavir Structure

N/A Structure

~%

Saquinavir Structure

3(S)-(tert-Butoxyformamido)-2(S)-hydroxy-4-phenyl-1-butanal Structure

3(S)-(tert-Buto...

~%

Saquinavir Structure

4(S)-(1(S)-Azido-2-phenylethyl)-1,3,2-dioxathiolane 2,2-dioxide Structure

4(S)-(1(S)-Azid...

~%

Saquinavir Structure

3(S)-(Benzyloxyformamido)-1-bromo-4-phenyl-2(S)-butanol Structure

3(S)-(Benzyloxy...

~%

Saquinavir Structure

4(S)-Benzyl-3-(tert-butoxycarbonyl)-2,2-dimethyl-5(R)-oxazolidineacetic acid chloride Structure

4(S)-Benzyl-3-(...

~%

Saquinavir Structure

Boc-L-phenylalanine Structure

Boc-L-phenylalanine

~%

Saquinavir Structure

N-Boc-L-phenylalaninal Structure

N-Boc-L-phenyla...

~%

Saquinavir Structure

N-tert-butyl-2-[2(R)-hydroxy-4-phenyl-3(S)-azidobutyl]decahydro(4aS,8aS)-isoquinoline-3(S)-carboxamide Structure

N-tert-butyl-2-...

~%

Saquinavir Structure

4(S)-Benzyl-3-(tert-butoxycarbonyl)-2,2-dimethyl-5(R)-oxazolidineacetic acid Structure

4(S)-Benzyl-3-(...

~%

Saquinavir Structure

ethyl (S)-4-benzyloxycarbonylamino-3-oxo-5-phenylpentanoate Structure

ethyl (S)-4-ben...

~%

Saquinavir Structure

4(S)-Benzyl-3-(benzyloxycarbonyl)-2,2-dimethyl-5(R)-oxazolidineacetic acid Structure

4(S)-Benzyl-3-(...

~%

Saquinavir Structure

N/A Structure

~%

Saquinavir Structure

Ethyl 4(S)-benzyl-3-(tert-butoxycarbonyl)-2,2-dimethyl-5(R)-oxazolidineacetate Structure

Ethyl 4(S)-benz...

~%

Saquinavir Structure

2(R)-(Methanesulfonyloxy)-4-phenyl-3(S)-phthalimido-1-butanol Structure

2(R)-(Methanesu...

~%

Saquinavir Structure

N/A Structure

~%

Saquinavir Structure

N/A Structure

~%

Saquinavir Structure

Ethyl 4(S)-benzyl-3-(benzyloxycarbonyl)-2,2-dimethyl-5(R)-oxazolidineacetate Structure

Ethyl 4(S)-benz...

~%

Saquinavir Structure

N/A Structure

~%

Saquinavir Structure

2-[2(R)-hydroxy-4-phenyl-3(S)-[[N-(phenylmethoxy)carbonyl]amino]butyl]-N-tert-butyldecahydro-(4aS,8aS)-isoquinoline-3(S)-carboxamide Structure

2-[2(R)-hydroxy...

~%

Saquinavir Structure

N/A Structure

~%

Saquinavir Structure

(1S,2S)-2-((tert-butoxycarbonyl)amino)-3-phenyl-1-(thiazol-2-yl)propyl acetate Structure

(1S,2S)-2-((ter...

~%

Saquinavir Structure

Quinoline-2-carboxylic acid Structure

Quinoline-2-car...

2-[3(S)-[(L-asparaginyl)-amino]-2(R)-hydroxy-4-phenylbutyl]-N-tert-butyl-decahydro(4aS,8aS)-isoquinoline-3(S)-carboxamide Structure

2-[3(S)-[(L-asp...

~%

Saquinavir Structure

Studies toward the large-scale synthesis of the HIV proteina...

[Parkes, Kevin E. B.; Bushnell, David J.; Crackett, Peter H.; Dunsdon, Stephen J.; Freeman, Andrew C.; et al. Journal of Organic Chemistry, 1994 , vol. 59, # 13 p. 3656 - 3664]

Reduction of peptide character of HIV protease inhibitors th...

[Journal of Medicinal Chemistry, , vol. 46, # 9 p. 1764 - 1768]

Studies toward the large-scale synthesis of the HIV proteina...

[Parkes, Kevin E. B.; Bushnell, David J.; Crackett, Peter H.; Dunsdon, Stephen J.; Freeman, Andrew C.; et al. Journal of Organic Chemistry, 1994 , vol. 59, # 13 p. 3656 - 3664]

The development of cyclic sulfolanes as novel and high-affin...

[Journal of Medicinal Chemistry, , vol. 37, # 8 p. 1177 - 1188]

Studies toward the large-scale synthesis of the HIV proteina...

[Parkes, Kevin E. B.; Bushnell, David J.; Crackett, Peter H.; Dunsdon, Stephen J.; Freeman, Andrew C.; et al. Journal of Organic Chemistry, 1994 , vol. 59, # 13 p. 3656 - 3664]