(2R)-1-(tert-butyldimethylsilyl)oxo-N-[(4-methylphenyl)sulfonyl]-2-amino-4-pentene

Base Information

• Chemical Name: (2R)-1-(tert-butyldimethylsilyl)oxo-N-[(4-methylphenyl)sulfonyl]-2-amino-4-pentene
• CAS No.: 486413-02-9
• Molecular Formula: C₁₈H₃₁NO₃SSi
• Molecular Weight: 369.601
• Mol file: 486413-02-9.mol

Synonyms:(2R)-1-(tert-butyldimethylsilyl)oxo-N-[(4-methylphenyl)sulfonyl]-2-amino-4-pentene

Chemical Property of (2R)-1-(tert-butyldimethylsilyl)oxo-N-[(4-methylphenyl)sulfonyl]-2-amino-4-pentene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R)-1-(tert-butyldimethylsilyl)oxo-N-[(4-methylphenyl)sulfonyl]-2-amino-4-pentene

There total 1 articles about (2R)-1-(tert-butyldimethylsilyl)oxo-N-[(4-methylphenyl)sulfonyl]-2-amino-4-pentene 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: 89.0%

vinyl magnesium bromide (1826-67-1) + (R)-2-(tert-butyldimethylsiloxy)methyl-1-(4-methylphenylsulfonyl)aziridine (188816-35-5) → (2R)-1-(tert-butyldimethylsilyl)oxo-N-[(4-methylphenyl)sulfonyl]-2-amino-4-pentene (486413-02-9)

Guidance literature:

vinyl magnesium bromide; With CuCN; In tetrahydrofuran; diethyl ether; at -78 ℃; for 0.333333h;

(R)-2-(tert-butyldimethylsiloxy)methyl-1-(4-methylphenylsulfonyl)aziridine; In tetrahydrofuran; diethyl ether; at 0 ℃; for 96h;

DOI:10.1016/S0040-4020(02)00725-1

Reference yield: 77.0%

(2R)-1-(tert-butyldimethylsilyl)oxo-N-[(4-methylphenyl)sulfonyl]-2-amino-4-pentene (486413-02-9) → (2R)-N-[(4-methylphenyl)sulfonyl]-2-amino-4-pentenol (486413-03-0)

Guidance literature:

With n-Bu₄F; In tetrahydrofuran; at 0 ℃; for 2h;

DOI:10.1016/S0040-4020(02)00725-1

Reference yield:

(2R)-1-(tert-butyldimethylsilyl)oxo-N-[(4-methylphenyl)sulfonyl]-2-amino-4-pentene (486413-02-9) → (3R)-3-(N-[(4-methylphenyl)sulfonyl]aminomethyl)-1-methylenecyclohexane (486413-09-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 77 percent / n-Bu₄F / tetrahydrofuran / 2 h / 0 °C

2.1: 90 percent / PPh₃; diethyl azodicarboxylate / tetrahydrofuran / 0 - 20 °C

3.1: 9-BBN / tetrahydrofuran / 0 - 20 °C

3.2: 58 percent / aq. K₃PO₄; PdCl₂(dppf)*CH₂Cl₂ / tetrahydrofuran; dimethylformamide / 18.5 h / 20 °C

4.1: 97 percent / BF₃*Et₂O / CH₂Cl₂ / 23 h / -78 - -25 °C

With 9-borabicyclo[3.3.1]nonane dimer; boron trifluoride diethyl etherate; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; 2.1: Mitsunobu reaction;

DOI:10.1016/S0040-4020(02)00725-1

upstream raw materials:

vinyl magnesium bromide

(R)-2-(tert-butyldimethylsiloxy)methyl-1-(4-methylphenylsulfonyl)aziridine

Downstream raw materials:

(2R)-N-[(4-methylphenyl)sulfonyl]-2-amino-4-pentenol

(2R)-2-[2-propenyl]-N-[(4-methylphenyl)sulfonyl]aziridine

(3R)-3-(N-[(4-methylphenyl)sulfonyl]aminomethyl)-1-methylenecyclohexane

N-(3-hydroxymethyl-cyclohexylmethyl)-4-methyl-benzenesulfonamide