N-benzyl-N-{(1R)-1-(Z)-[(1S)-2-((3aR,8aS)-2,2-dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-1-hydroxy-2-oxoethyl]but-2-enyl}-4-methylbenzenesulfonamide

Base Information

• Chemical Name: N-benzyl-N-{(1R)-1-(Z)-[(1S)-2-((3aR,8aS)-2,2-dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-1-hydroxy-2-oxoethyl]but-2-enyl}-4-methylbenzenesulfonamide
• CAS No.: 1300117-27-4
• Molecular Formula: C₃₂H₃₆N₂O₅S
• Molecular Weight: 560.714
• Mol file: 1300117-27-4.mol

Synonyms:

Chemical Property of N-benzyl-N-{(1R)-1-(Z)-[(1S)-2-((3aR,8aS)-2,2-dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-1-hydroxy-2-oxoethyl]but-2-enyl}-4-methylbenzenesulfonamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-benzyl-N-{(1R)-1-(Z)-[(1S)-2-((3aR,8aS)-2,2-dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-1-hydroxy-2-oxoethyl]but-2-enyl}-4-methylbenzenesulfonamide

There total 4 articles about N-benzyl-N-{(1R)-1-(Z)-[(1S)-2-((3aR,8aS)-2,2-dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-1-hydroxy-2-oxoethyl]but-2-enyl}-4-methylbenzenesulfonamide 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: 19.0%

N-benzyl-N-{(E)-(3R)-[2-((3aR,8aS)-2,2-dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]-oxazol-3-yl)-2-oxoethoxy]but-1-enyl}-4-methylbenzenesulfonamide (1300117-26-3) → N-benzyl-N-{(1R)-1-[(1S)-2-((3aR,8aS)-2,2-dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-1-hydroxy-2-oxoethyl]but-2-enyl}-4-methylbenzenesulfonamide + N-benzyl-N-{(1R)-1-(E)-[(1S)-2-((3aR,8aS)-2,2-dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-1-hydroxy-2-oxoethyl]but-2-enyl}-4-methylbenzenesulfonamide (1300117-28-5) + N-benzyl-N-{(1R)-1-(Z)-[(1S)-2-((3aR,8aS)-2,2-dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-1-hydroxy-2-oxoethyl]but-2-enyl}-4-methylbenzenesulfonamide (1300117-27-4)

Guidance literature:

With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 1h; optical yield given as %de; stereoselective reaction;

DOI:10.1002/chem.201003265

Reference yield:

(R)-N-benzyl-N-(3-hydroxybut-1-yn-1-yl)-4-methylbenzenesulfonamide (1300116-93-1) → N-benzyl-N-{(1R)-1-(Z)-[(1S)-2-((3aR,8aS)-2,2-dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-1-hydroxy-2-oxoethyl]but-2-enyl}-4-methylbenzenesulfonamide (1300117-27-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium bis(2-methoxyethoxy)aluminium dihydride / tetrahydrofuran; toluene / 0.5 h / 20 °C

2.1: tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide / water; toluene / 3 h / 20 °C

2.2: 0.5 h / 20 °C

3.1: N,N,N,N,N,N-hexamethylphosphoric triamide; lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; tetra(n-butyl)ammonium hydrogensulfate; sodium bis(2-methoxyethoxy)aluminium dihydride; sodium hydroxide; lithium hexamethyldisilazane; In tetrahydrofuran; water; toluene; 3.1: Wittig rearrangement;

DOI:10.1002/chem.201003265

Reference yield:

N-benzyl-N-[(3R)-3-(tert-butyldiphenylsilyloxy)but-1-ynyl]-4-methylbenzenesulfonamide (1300116-89-5) → N-benzyl-N-{(1R)-1-(Z)-[(1S)-2-((3aR,8aS)-2,2-dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-1-hydroxy-2-oxoethyl]but-2-enyl}-4-methylbenzenesulfonamide (1300117-27-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 - 20 °C

2.1: sodium bis(2-methoxyethoxy)aluminium dihydride / tetrahydrofuran; toluene / 0.5 h / 20 °C

3.1: tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide / water; toluene / 3 h / 20 °C

3.2: 0.5 h / 20 °C

4.1: N,N,N,N,N,N-hexamethylphosphoric triamide; lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; tetrabutyl ammonium fluoride; tetra(n-butyl)ammonium hydrogensulfate; sodium bis(2-methoxyethoxy)aluminium dihydride; sodium hydroxide; lithium hexamethyldisilazane; In tetrahydrofuran; water; toluene; 4.1: Wittig rearrangement;

DOI:10.1002/chem.201003265

upstream raw materials:

N-benzyl-N-{(E)-(3R)-[2-((3aR,8aS)-2,2-dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]-oxazol-3-yl)-2-oxoethoxy]but-1-enyl}-4-methylbenzenesulfonamide

(R)-N-benzyl-N-(3-hydroxybut-1-yn-1-yl)-4-methylbenzenesulfonamide

N-benzyl-N-[(3R)-3-(tert-butyldiphenylsilyloxy)but-1-ynyl]-4-methylbenzenesulfonamide

N-benzyl-N-((E)-(3R)-3-hydroxybut-1-enyl)-4-methylbenzenesulfonamide

Downstream raw materials:

N-benzyl-N-[(3R)-((4S)-4-hydroxy-5-oxo-tetrahydrofuran-3-yl)]-4-methylbenzenesulfonamide

methyl (Z)-(2S,3R)-3-[benzyl(4-methylbenzenesulfonyl)amino]-2-hydroxy-hex-4-enoate