2-Methyl-propane-2-sulfinic acid (1R,2S)-1-(2,4,6-trimethyl-benzenesulfonylamino)-indan-2-yl ester

Base Information

• Chemical Name: 2-Methyl-propane-2-sulfinic acid (1R,2S)-1-(2,4,6-trimethyl-benzenesulfonylamino)-indan-2-yl ester
• CAS No.: 446021-65-4
• Molecular Formula: C₂₂H₂₉NO₄S₂
• Molecular Weight: 435.609
• Mol file: 446021-65-4.mol

Synonyms:2-Methyl-propane-2-sulfinic acid (1R,2S)-1-(2,4,6-trimethyl-benzenesulfonylamino)-indan-2-yl ester

Chemical Property of 2-Methyl-propane-2-sulfinic acid (1R,2S)-1-(2,4,6-trimethyl-benzenesulfonylamino)-indan-2-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-Methyl-propane-2-sulfinic acid (1R,2S)-1-(2,4,6-trimethyl-benzenesulfonylamino)-indan-2-yl ester

There total 7 articles about 2-Methyl-propane-2-sulfinic acid (1R,2S)-1-(2,4,6-trimethyl-benzenesulfonylamino)-indan-2-yl ester 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: 97.0%

tert-butylmagnesium chloride (677-22-5) + (2S,3aR,8aS)-3-(mesitylsulfonyl)-3,3a,8,8a-tetrahydroindeno[1,2-d][1,2,3]oxathiazole-2-oxide (446021-62-1) → 2-Methyl-propane-2-sulfinic acid (1R,2S)-1-(2,4,6-trimethyl-benzenesulfonylamino)-indan-2-yl ester (446021-65-4)

Guidance literature:

In tetrahydrofuran; at -45 - -15 ℃;

DOI:10.1016/j.tet.2005.03.122

Reference yield:

N-((1R,2S)-2-Hydroxy-indan-1-yl)-2,4,6-trimethyl-benzenesulfonamide (175848-32-5) → 2-Methyl-propane-2-sulfinic acid (1R,2S)-1-(2,4,6-trimethyl-benzenesulfonylamino)-indan-2-yl ester (446021-65-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / thionyl chloride; 3,5-lutidine / tetrahydrofuran / -45 °C

2: 97 percent / tetrahydrofuran / -45 - -15 °C

With 3,5-Lutidine; thionyl chloride; In tetrahydrofuran;

DOI:10.1016/j.tet.2005.03.122

Reference yield:

2-mesitylenesulphonyl chloride (773-64-8) → 2-Methyl-propane-2-sulfinic acid (1R,2S)-1-(2,4,6-trimethyl-benzenesulfonylamino)-indan-2-yl ester (446021-65-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 94 percent / Na₂CO₃ / H₂O; ethyl acetate; tetrahydrofuran / 20 °C

2: 8 percent / thionyl chloride; triethylamine / tetrahydrofuran / -45 °C

3: tetrahydrofuran / -78 - -10 °C

With thionyl chloride; sodium carbonate; triethylamine; In tetrahydrofuran; water; ethyl acetate;

DOI:10.1021/ja0200692

upstream raw materials:

tert-butylmagnesium bromide

(2S,3aR,8aS)-3-(2,4,6-Trimethyl-benzenesulfonyl)-3,3a,8,8a-tetrahydro-1-oxa-2-thia-3-aza-cyclopenta[a]indene 2-oxide

tert-butylmagnesium chloride

(2S,3aR,8aS)-3-(mesitylsulfonyl)-3,3a,8,8a-tetrahydroindeno[1,2-d][1,2,3]oxathiazole-2-oxide

Downstream raw materials:

(2S,3aR,8aS)-3-(2,4,6-Trimethyl-benzenesulfonyl)-3,3a,8,8a-tetrahydro-1-oxa-2-thia-3-aza-cyclopenta[a]indene 2-oxide

(R)-2-methylpropane-2-sulfinamide

(R)-(tert-butylsulfinyl)benzene

N-((1R,2S)-2-Hydroxy-indan-1-yl)-2,4,6-trimethyl-benzenesulfonamide

Refernces

• 1、 Han, Zhengxu,Krishnamurthy, Dhileepkumar,Grover, Paul,Wilkinson, H. Scott,Fang, Q. Kevin,Su, Xiping,Lu, Zhi-Hui,Magiera, Daniel,Senanayake, Chris H.. "A highly selective and practical method for enantiopure sulfoxides utilizing activated and functionally differentiated N-sulfonyl-1,2,3-oxathiazolidine-2-oxide derivatives". . p. 2032 - 2035. Retrieved 2007/10/03.