(S)-2-(tert-butoxycarbonylamino)-3-((R)-tetrahydro-2H-pyran-3-yl)propyl 4-methylbenzenesulfonate

Base Information

• Chemical Name: (S)-2-(tert-butoxycarbonylamino)-3-((R)-tetrahydro-2H-pyran-3-yl)propyl 4-methylbenzenesulfonate
• CAS No.: 942145-23-5
• Molecular Formula: C₂₀H₃₁NO₆S
• Molecular Weight: 413.535
• Mol file: 942145-23-5.mol

Synonyms:(S)-2-(tert-butoxycarbonylamino)-3-((R)-tetrahydro-2H-pyran-3-yl)propyl 4-methylbenzenesulfonate

Chemical Property of (S)-2-(tert-butoxycarbonylamino)-3-((R)-tetrahydro-2H-pyran-3-yl)propyl 4-methylbenzenesulfonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-(tert-butoxycarbonylamino)-3-((R)-tetrahydro-2H-pyran-3-yl)propyl 4-methylbenzenesulfonate

There total 10 articles about (S)-2-(tert-butoxycarbonylamino)-3-((R)-tetrahydro-2H-pyran-3-yl)propyl 4-methylbenzenesulfonate 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:

tert-butyl (S)-1-hydroxy-3-((R)-tetrahydro-2H-pyran-3-yl)propan-2-ylcarbamate (942144-43-6,942144-42-5) + p-toluenesulfonyl chloride (98-59-9) → (S)-2-(tert-butoxycarbonylamino)-3-((R)-tetrahydro-2H-pyran-3-yl)propyl 4-methylbenzenesulfonate (942145-23-5)

Guidance literature:

With pyridine; In dichloromethane; at 20 ℃; for 16h;

DOI:10.1021/ml200137x

Reference yield:

tert-butyl (2S,4R)-1-hydroxy-4-(hydroxymethyl)hept-6-en-2-ylcarbamate (942144-12-9) → (S)-2-(tert-butoxycarbonylamino)-3-((R)-tetrahydro-2H-pyran-3-yl)propyl 4-methylbenzenesulfonate (942145-23-5)

Guidance literature:

Multi-step reaction with 7 steps

1.1: toluene-4-sulfonic acid / acetone / 1 h / -20 - 20 °C

2.1: 1H-imidazole; dmap / dichloromethane / 16 h / 20 °C

3.1: dimethylsulfide borane complex / tetrahydrofuran / 5 h / Cooling with ice

3.2: 16 h / 20 °C

4.1: triethylamine / dichloromethane / 1 h / 0 - 20 °C

5.1: tetraethylammonium fluoride / tetrahydrofuran / 16 h / Reflux

6.1: water; acetic acid / 1.5 h / Heating

7.1: pyridine / dichloromethane / 16 h / 20 °C

With pyridine; 1H-imidazole; dmap; dimethylsulfide borane complex; water; tetraethylammonium fluoride; toluene-4-sulfonic acid; acetic acid; triethylamine; In tetrahydrofuran; dichloromethane; acetone;

DOI:10.1021/ml200137x

Reference yield:

(S)-tert-butyl 4-((R)-2-(hydroxymethyl)pent-4-enyl)-2,2-dimethyloxazolidine-3-carboxylate (942144-13-0) → (S)-2-(tert-butoxycarbonylamino)-3-((R)-tetrahydro-2H-pyran-3-yl)propyl 4-methylbenzenesulfonate (942145-23-5)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 1H-imidazole; dmap / dichloromethane / 16 h / 20 °C

2.1: dimethylsulfide borane complex / tetrahydrofuran / 5 h / Cooling with ice

2.2: 16 h / 20 °C

3.1: triethylamine / dichloromethane / 1 h / 0 - 20 °C

4.1: tetraethylammonium fluoride / tetrahydrofuran / 16 h / Reflux

5.1: water; acetic acid / 1.5 h / Heating

6.1: pyridine / dichloromethane / 16 h / 20 °C

With pyridine; 1H-imidazole; dmap; dimethylsulfide borane complex; water; tetraethylammonium fluoride; acetic acid; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ml200137x

upstream raw materials:

tert-butyl (S)-1-hydroxy-3-((R)-tetrahydro-2H-pyran-3-yl)propan-2-ylcarbamate

p-toluenesulfonyl chloride

tert-butyl (2S,4R)-1-hydroxy-4-(hydroxymethyl)hept-6-en-2-ylcarbamate

(S)-tert-butyl 4-((R)-2-(hydroxymethyl)pent-4-enyl)-2,2-dimethyloxazolidine-3-carboxylate

Downstream raw materials:

methyl 2-((R)-(3-chlorophenyl)((R)-1-((S)-2-(methylamino)-3-((R)-tetrahydro-2H-pyran-3-yl)propylcarbamoyl)piperidin-3-yl)methoxy)ethylcarbamate trifluoroacetate

tert-butyl (S)-1-azido-3-((R)-tetrahydro-2H-pyran-3-yl)propan-2-yl(methyl)carbamate

tert-butyl (S)-1-amino-3-((R)-tetrahydro-2H-pyran-3-yl)propan-2-yl(methyl)carbamate

[2-{3-[(3-chloro-5-fluoro-phenyl)-((S)-2-methoxycarbonylamino-ethoxy)-methyl]-benzoylamino}-1-((R)-tetrahydro-pyran-3-ylmethyl)-ethyl]-methyl-carbamic acid tert-butyl ester