(S)-1-(4-bromo-1-tosyl-1H-indol-3-yl)-4-[(2R,5S)-2-phenyl-3-tosyl-1,3-oxazinan-5-yl]but-3-yn-2-ol

Base Information

• Chemical Name: (S)-1-(4-bromo-1-tosyl-1H-indol-3-yl)-4-[(2R,5S)-2-phenyl-3-tosyl-1,3-oxazinan-5-yl]but-3-yn-2-ol
• CAS No.: 1273006-13-5
• Molecular Formula: C₃₆H₃₃BrN₂O₆S₂
• Molecular Weight: 733.704
• Mol file: 1273006-13-5.mol

Synonyms:(S)-1-(4-bromo-1-tosyl-1H-indol-3-yl)-4-[(2R,5S)-2-phenyl-3-tosyl-1,3-oxazinan-5-yl]but-3-yn-2-ol

Chemical Property of (S)-1-(4-bromo-1-tosyl-1H-indol-3-yl)-4-[(2R,5S)-2-phenyl-3-tosyl-1,3-oxazinan-5-yl]but-3-yn-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-1-(4-bromo-1-tosyl-1H-indol-3-yl)-4-[(2R,5S)-2-phenyl-3-tosyl-1,3-oxazinan-5-yl]but-3-yn-2-ol

There total 15 articles about (S)-1-(4-bromo-1-tosyl-1H-indol-3-yl)-4-[(2R,5S)-2-phenyl-3-tosyl-1,3-oxazinan-5-yl]but-3-yn-2-ol 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: 69.0%

1-(4-bromo-1-tosyl-1H-indol-3-yl)-4-[(2R,5S)-2-phenyl-3-tosyl-1,3-oxazinan-5-yl]but-3-yn-2-one (1273005-95-0) → (S)-1-(4-bromo-1-tosyl-1H-indol-3-yl)-4-[(2R,5S)-2-phenyl-3-tosyl-1,3-oxazinan-5-yl]but-3-yn-2-ol (1273006-13-5)

Guidance literature:

With S-(+)-Alpine-borane; In tetrahydrofuran; at 0 - 20 ℃; optical yield given as %de; diastereoselective reaction; Inert atmosphere;

DOI:10.1021/jo102388e

Reference yield:

(2R)-2-ethynyl-N-(4-methylphenylsulfonyl)aziridine (742078-20-2) → (S)-1-(4-bromo-1-tosyl-1H-indol-3-yl)-4-[(2R,5S)-2-phenyl-3-tosyl-1,3-oxazinan-5-yl]but-3-yn-2-ol (1273006-13-5)

Guidance literature:

Multi-step reaction with 4 steps

1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; indium iodide / tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; water / 2.5 h / 20 °C / Inert atmosphere

2: 10-camphorsufonic acid / 1,2-dichloro-ethane / 14 h / 70 °C

3: copper(l) iodide; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; trifuran-2-yl-phosphane; triethylamine / N,N-dimethyl-formamide / 50 °C

4: S-(+)-Alpine-borane / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; indium iodide; trifuran-2-yl-phosphane; S-(+)-Alpine-borane; 10-camphorsufonic acid; triethylamine; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1021/jo102388e

Reference yield:

2-(4-bromo-1-tosyl-1H-indol-3-yl)acetaldehyde (1273005-83-6) + (2R,5S)-5-ethynyl-2-phenyl-3-tosyl-1,3-oxazinane (1273005-88-1) → (S)-1-(4-bromo-1-tosyl-1H-indol-3-yl)-4-[(2R,5S)-2-phenyl-3-tosyl-1,3-oxazinan-5-yl]but-3-yn-2-ol (1273006-13-5) + (R)-1-(4-bromo-1-tosyl-1H-indol-3-yl)-4-[(2R,5S)-2-phenyl-3-tosyl-1,3-oxazinan-5-yl]but-3-yn-2-ol (1273006-07-7)

Guidance literature:

With n-butyllithium; cerium(III) chloride; In tetrahydrofuran; at -78 ℃; Inert atmosphere;

DOI:10.1021/jo102388e

upstream raw materials:

4-bromo-1H-indole

S-ethyl 2-(4-bromo-1-tosyl-1H-indol-3-yl)ethanethioate

2-(4-bromo-1-tosyl-1H-indol-3-yl)acetaldehyde

(2R,5S)-5-ethynyl-2-phenyl-3-tosyl-1,3-oxazinane

Downstream raw materials:

[(6aS,9S)-4,7-ditosyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinolin-9-yl]methanol

[(6aR,9S)-4,7-ditosyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinolin-9-yl]methanol