(R)-1-Azido-4-(Methylsulfinyl)-butane

Base Information

• Chemical Name: (R)-1-Azido-4-(Methylsulfinyl)-butane
• CAS No.: 155185-01-6
• Molecular Formula: C₅H₁₁N₃OS
• Molecular Weight: 161.228
• Mol file: 155185-01-6.mol

Synonyms:(R)-1-Azido-4-(Methylsulfinyl)-butane

Chemical Property of (R)-1-Azido-4-(Methylsulfinyl)-butane

Chemical Property:

• PSA: 86.03000
• LogP: 1.77386
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Slightly), Methanol (Slightly)

Purity/Quality:

98% ^*data from raw suppliers

(R)-1-Azido-4-(methylsulfinyl)-butane ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: (R)-1-Azido-4-(Methylsulfinyl)-butane can be used in the preparation of (R)-Sulforaphane (S699105).

Technology Process of (R)-1-Azido-4-(Methylsulfinyl)-butane

There total 4 articles about (R)-1-Azido-4-(Methylsulfinyl)-butane 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: 93.0%

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 3-O-((S)-4-azidobutanesulfinate) (1176244-24-8) + methylmagnesium chloride (676-58-4) → (R)-4-Azidobutyl methyl sulfoxide (155185-01-6)

Guidance literature:

In toluene; at 0 ℃; for 1h; Inert atmosphere;

DOI:10.1021/jo9007749

Reference yield:

Methanesulfonic acid 4-((R)-methanesulfinyl)-butyl ester → (R)-4-Azidobutyl methyl sulfoxide (155185-01-6)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; for 12h; Yield given; Ambient temperature;

DOI:10.1021/jo00082a016

Reference yield:

(R)-4-Hydroxybutyl methyl sulfoxide (155184-99-9) → (R)-4-Azidobutyl methyl sulfoxide (155185-01-6)

Guidance literature:

Multi-step reaction with 2 steps

1: Et₃N / CH₂Cl₂ / 2 h / 0 °C

2: NaN₃ / dimethylformamide / 12 h / Ambient temperature

With sodium azide; triethylamine; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00082a016

upstream raw materials:

(R)-4-Hydroxybutyl methyl sulfoxide

(R)-4-(tert-Butyldimethylsiloxy)butyl methyl sulfoxide

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 3-O-((S)-4-azidobutanesulfinate)

methylmagnesium chloride

Refernces

• 1、 Whitesell, James K.,Wong, Man-Shing. "Asymmetric Synthesis of Chiral Sulfinate Esters and Sulfoxides. Synthesis of Sulforaphane". . p. 597 - 601. Retrieved 2007/10/02.