[(1S,2R)-1-Benzyl-3-((3S,4aS,7aS)-3-tert-butylcarbamoyl-octahydro-[2]pyrindin-2-yl)-2-hydroxy-propyl]-carbamic acid (2S,3S)-2-methyl-tetrahydro-thiophen-3-yl ester

Base Information

• Chemical Name: [(1S,2R)-1-Benzyl-3-((3S,4aS,7aS)-3-tert-butylcarbamoyl-octahydro-[2]pyrindin-2-yl)-2-hydroxy-propyl]-carbamic acid (2S,3S)-2-methyl-tetrahydro-thiophen-3-yl ester
• CAS No.: 1053616-98-0
• Molecular Formula: C₂₉H₄₅N₃O₄S
• Molecular Weight: 531.76

Synonyms:[(1S,2R)-1-Benzyl-3-((3S,4aS,7aS)-3-tert-butylcarbamoyl-octahydro-[2]pyrindin-2-yl)-2-hydroxy-propyl]-carbamic acid (2S,3S)-2-methyl-tetrahydro-thiophen-3-yl ester

Chemical Property of [(1S,2R)-1-Benzyl-3-((3S,4aS,7aS)-3-tert-butylcarbamoyl-octahydro-[2]pyrindin-2-yl)-2-hydroxy-propyl]-carbamic acid (2S,3S)-2-methyl-tetrahydro-thiophen-3-yl ester

Chemical Property:

Purity/Quality:

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Technology Process of [(1S,2R)-1-Benzyl-3-((3S,4aS,7aS)-3-tert-butylcarbamoyl-octahydro-[2]pyrindin-2-yl)-2-hydroxy-propyl]-carbamic acid (2S,3S)-2-methyl-tetrahydro-thiophen-3-yl ester

There total 16 articles about [(1S,2R)-1-Benzyl-3-((3S,4aS,7aS)-3-tert-butylcarbamoyl-octahydro-[2]pyrindin-2-yl)-2-hydroxy-propyl]-carbamic acid (2S,3S)-2-methyl-tetrahydro-thiophen-3-yl ester 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:

cyclopentane-cis-1,2-dicarboxylic acid anhydride (35878-28-5,743438-34-8) → [(1S,2R)-1-Benzyl-3-((3S,4aS,7aS)-3-tert-butylcarbamoyl-octahydro-[2]pyrindin-2-yl)-2-hydroxy-propyl]-carbamic acid (2S,3S)-2-methyl-tetrahydro-thiophen-3-yl ester (1053616-98-0)

Guidance literature:

Multi-step reaction with 10 steps

1: 3 h / Heating

3: 23 g / oxalyl chloride / toluene / 28 h

4: 20 g / H₂, 2,6-lutidine / 10percent Pd/C / tetrahydrofuran / 18 h / 2585.7 Torr

5: 1.) lithium bis(trimethylsilyl)amide, 3.) AcOH

6: 12 g / H₂ / 5percent Pd/C / tetrahydrofuran / 2585.7 Torr

7: 68 percent / BH₃*Me₂S / tetrahydrofuran / 3 h / 25 °C

8: trimethylaluminum / tetrahydrofuran; toluene / 24 h / 25 °C

9: 39 percent / propan-2-ol / 80 °C

10: H₂, Et₃N / 10percent Pd/C / tetrahydrofuran / 48 h

With 2,6-dimethylpyridine; oxalyl dichloride; dimethylsulfide borane complex; hydrogen; trimethylaluminum; acetic acid; triethylamine; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; isopropyl alcohol; toluene;

DOI:10.1021/jm00034a016

Reference yield:

2(S)-methyl-3(R)-hydroxytetrahydrothiophene (121153-33-1) → [(1S,2R)-1-Benzyl-3-((3S,4aS,7aS)-3-tert-butylcarbamoyl-octahydro-[2]pyrindin-2-yl)-2-hydroxy-propyl]-carbamic acid (2S,3S)-2-methyl-tetrahydro-thiophen-3-yl ester (1053616-98-0)

Guidance literature:

Multi-step reaction with 2 steps

1: Et₃N / CH₂Cl₂ / 12 h / 24 °C

2: H₂, Et₃N / 10percent Pd/C / tetrahydrofuran / 48 h

With hydrogen; triethylamine; palladium on activated charcoal; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jm00034a016

Reference yield:

3-hydroxy-4-pentanolide of (3S,4R)-3,4-dihydroxypentanoic acid (88400-20-8) → [(1S,2R)-1-Benzyl-3-((3S,4aS,7aS)-3-tert-butylcarbamoyl-octahydro-[2]pyrindin-2-yl)-2-hydroxy-propyl]-carbamic acid (2S,3S)-2-methyl-tetrahydro-thiophen-3-yl ester (1053616-98-0)

Guidance literature:

Multi-step reaction with 7 steps

1: diisopropylethylamine, 4-(dimethylamino)pyridine / CH₂Cl₂ / 12 h

2: LiAlH₄ / diethyl ether / 2 h / Heating

3: Et₃N / CH₂Cl₂ / 12 h / -40 - 24 °C

4: Li₂S / dimethylformamide / 6 h / 60 °C

5: thiophenol, BF₃*OEt₂ / CH₂Cl₂ / 1.5 h / 0 - 24 °C

6: Et₃N / CH₂Cl₂ / 12 h / 24 °C

7: H₂, Et₃N / 10percent Pd/C / tetrahydrofuran / 48 h

With dmap; lithium aluminium tetrahydride; lithium sulfide; boron trifluoride diethyl etherate; hydrogen; thiophenol; triethylamine; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm00034a016

upstream raw materials:

N-tert-butyl-2-<2(R)-hydroxy-4-phenyl-3(S)-azidobutyl>octahydro-(3S,4aS,7aS)-1H-pyrindene-3(S)-carboxamide

cyclopentane-cis-1,2-dicarboxylic acid anhydride

2(S)-methyl-3(R)-hydroxytetrahydrothiophene

3-hydroxy-4-pentanolide of (3S,4R)-3,4-dihydroxypentanoic acid

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