HIV-RT inhibitor 1

Base Information

• Chemical Name: HIV-RT inhibitor 1
• CAS No.: 1443460-91-0
• Molecular Formula: C₄₈H₇₃ClN₂O₆
• Molecular Weight: 809.57
• Mol file: 1443460-91-0.mol

Synonyms:4-(((3aR,5aR,5bR,7aR,9S,11aR,11bR,13aS)-3a-((R)-2-((4-chlorobenzyl)(2-(dimethylamino)ethyl)amino)-1-hydroxyethyl)-1-isopropyl-5a,5b,8,8,11a-pentamethyl-2-oxo-3,3a,4,5,5a,5b,6,7,7a,8,9,10,11,11a,11b,12,13,13a-octadecahydro-2H-cyclopenta[a]chrysen-9-yl)oxy)-2,2-dimethyl-4-oxobutanoic acid

Chemical Property of HIV-RT inhibitor 1

Chemical Property:

• Boiling Point: 817.1±65.0 °C(Predicted)
• PKA: 4.48±0.28(Predicted)
• Density: 1.17±0.1 g/cm3(Predicted)

Purity/Quality:

99%, ^*data from raw suppliers

GSK2838232 98+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Description: GSK2838232 is a second generation inhibitor of HIV-1 maturation (IC90 = 6.4 nM). It is active against a variety of HIV isolates resistant to bevirimat (PA-457; ).

Technology Process of HIV-RT inhibitor 1

There total 16 articles about HIV-RT inhibitor 1 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:

1-tert-butyl 4-((3aR,5aR,5bR,9S,11aR)-3a-formyl-1-isopropyl-5a,5b,8,8,11a-pentamethyl-2-oxo-3,3a,4,5,5a,5b,6,7,7a,8,9,10,11,11a,11b,12,13,13a-octadecahydro-2H-cyclopenta[a]chrysen-9-yl) 2,2-dimethylsuccinate → 4-(((3aR,5aR,5bR,7aR,9S,11aR,11bR,13aS)-3a-((R)-2-((4-chlorobenzyl)(2-(dimethylamino)ethyl)amino)-1-hydroxyethyl)-1-isopropyl-5a,5b,8,8,11a-pentamethyl-2-oxo-3,3a,4,5,5a,5b,6,7,7a,8,9,10,11,11a,11b,12,13,13a-octadecahydro-2H-cyclopenta[a]chrysen-9-yl)oxy)-2,2-dimethyl-4-oxobutanoic acid (1443460-91-0)

Guidance literature:

Multi-step reaction with 5 steps

1: N-[(1S,2S,4S)-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl]-2-pyridinemethanamine; copper(II) acetate monohydrate; N-ethyl-N,N-diisopropylamine / toluene; tert-butyl alcohol / 2 h / 30 °C

2: hydrogen; 1% platinum on charcoal / ethanol / 10 h / 50 °C / 3000.3 - 3750.38 Torr

3: triethylamine; magnesium sulfate / methanol

4: toluene-4-sulfonic acid / acetonitrile / 2 h / 65 °C

5: sodium cyanoborohydride; sodium acetate / methanol

With N-[(1S,2S,4S)-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl]-2-pyridinemethanamine; 1% platinum on charcoal; hydrogen; sodium acetate; copper(II) acetate monohydrate; sodium cyanoborohydride; magnesium sulfate; toluene-4-sulfonic acid; triethylamine; N-ethyl-N,N-diisopropylamine; In methanol; ethanol; toluene; acetonitrile; tert-butyl alcohol;

DOI:10.1021/acs.oprd.1c00374

Reference yield:

C36H57NO3 → 4-(((3aR,5aR,5bR,7aR,9S,11aR,11bR,13aS)-3a-((R)-2-((4-chlorobenzyl)(2-(dimethylamino)ethyl)amino)-1-hydroxyethyl)-1-isopropyl-5a,5b,8,8,11a-pentamethyl-2-oxo-3,3a,4,5,5a,5b,6,7,7a,8,9,10,11,11a,11b,12,13,13a-octadecahydro-2H-cyclopenta[a]chrysen-9-yl)oxy)-2,2-dimethyl-4-oxobutanoic acid (1443460-91-0)

Guidance literature:

Multi-step reaction with 7 steps

1.1: potassium hydroxide / methanol; tetrahydrofuran

2.1: triethylamine / tetrahydrofuran / 1 h / 0 °C

2.2: 1.5 h

3.1: copper(II) acetate monohydrate; N-ethyl-N,N-diisopropylamine; C₂₆H₃₂N₂O₂ / toluene; tert-butyl alcohol / 40 h

4.1: hydrogen; 1% platinum on charcoal / ethanol / 10 h / 50 °C / 3000.3 - 3750.38 Torr

5.1: triethylamine; magnesium sulfate / methanol

6.1: toluene-4-sulfonic acid / acetonitrile / 2 h / 65 °C

7.1: sodium cyanoborohydride; sodium acetate / methanol

With 1% platinum on charcoal; hydrogen; sodium acetate; copper(II) acetate monohydrate; C₂₆H₃₂N₂O₂; sodium cyanoborohydride; magnesium sulfate; toluene-4-sulfonic acid; triethylamine; N-ethyl-N,N-diisopropylamine; potassium hydroxide; In tetrahydrofuran; methanol; ethanol; toluene; acetonitrile; tert-butyl alcohol;

DOI:10.1021/acs.oprd.1c00374

Reference yield:

(3aR,5aR,5bR,7aR,9S,11aR,11bR,13aS)-9-Hydroxy-3a-(hydroxymethyl)-1-isopropyl-5a,5b,8,8,11a-pentamethyl-3,3a,4,5,5a,5b,6,7,7a,8,9,10,11,11a,11b,12,13,13a-octadecahydro-2H-cyclopenta[a]chrysene-2-one (154955-52-9) → 4-(((3aR,5aR,5bR,7aR,9S,11aR,11bR,13aS)-3a-((R)-2-((4-chlorobenzyl)(2-(dimethylamino)ethyl)amino)-1-hydroxyethyl)-1-isopropyl-5a,5b,8,8,11a-pentamethyl-2-oxo-3,3a,4,5,5a,5b,6,7,7a,8,9,10,11,11a,11b,12,13,13a-octadecahydro-2H-cyclopenta[a]chrysen-9-yl)oxy)-2,2-dimethyl-4-oxobutanoic acid (1443460-91-0)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; water; tetrabutyl-ammonium chloride; N-chloro-succinimide / tetrahydrofuran

2.1: triethylamine / tetrahydrofuran / 1 h / 0 °C

2.2: 1.5 h

3.1: copper(II) acetate monohydrate; N-ethyl-N,N-diisopropylamine; C₂₆H₃₂N₂O₂ / toluene; tert-butyl alcohol / 40 h

4.1: hydrogen; 1% platinum on charcoal / ethanol / 10 h / 50 °C / 3000.3 - 3750.38 Torr

5.1: triethylamine; magnesium sulfate / methanol

6.1: toluene-4-sulfonic acid / acetonitrile / 2 h / 65 °C

7.1: sodium cyanoborohydride; sodium acetate / methanol

With N-chloro-succinimide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; 1% platinum on charcoal; tetrabutyl-ammonium chloride; water; hydrogen; sodium acetate; copper(II) acetate monohydrate; C₂₆H₃₂N₂O₂; sodium cyanoborohydride; magnesium sulfate; toluene-4-sulfonic acid; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; ethanol; toluene; acetonitrile; tert-butyl alcohol;

DOI:10.1021/acs.oprd.1c00374

upstream raw materials:

(3aR,5aR,5bR,7aR,9S,11aR,11bR,13aS)-9-Hydroxy-3a-(hydroxymethyl)-1-isopropyl-5a,5b,8,8,11a-pentamethyl-3,3a,4,5,5a,5b,6,7,7a,8,9,10,11,11a,11b,12,13,13a-octadecahydro-2H-cyclopenta[a]chrysene-2-one

(3aR,5aR,5bR,7aR,9S,11aR,11bR,13aS)-3a-(hydroxymethyl)-1-isopropyl-5a,5b,8, 8,11a-pentamethyl-2-oxo-3,3a,4,5,5a,5b,6,7,7a,8,9,10,11,11a,11b,12,13,13a-octadecahydro-2H-cyclopenta[a]chrysen-9-yl acetate

(3aR,5aR,5bR,7aR,9S,11aR,11bR,13aS)-3a-formyl-1-isopropyl-5a,5b,8,8,11a-pentamethyl-2-oxo-3,3a,4,5,5a,5b,6,7,7a,8,9,10,11,11a,11b,12,13,13a-octadecahydro-2H-cyclopenta[a]chrysen-9-yl acetate

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