Adamantane-1-sulfinic acid (1R,2S)-1-phenyl-2-(toluene-4-sulfonylamino)-propyl ester

Base Information

• Chemical Name: Adamantane-1-sulfinic acid (1R,2S)-1-phenyl-2-(toluene-4-sulfonylamino)-propyl ester
• CAS No.: 594836-48-3
• Molecular Formula: C₂₆H₃₃NO₄S₂
• Molecular Weight: 487.684
• Mol file: 594836-48-3.mol

Synonyms:Adamantane-1-sulfinic acid (1R,2S)-1-phenyl-2-(toluene-4-sulfonylamino)-propyl ester

Chemical Property of Adamantane-1-sulfinic acid (1R,2S)-1-phenyl-2-(toluene-4-sulfonylamino)-propyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Adamantane-1-sulfinic acid (1R,2S)-1-phenyl-2-(toluene-4-sulfonylamino)-propyl ester

There total 2 articles about Adamantane-1-sulfinic acid (1R,2S)-1-phenyl-2-(toluene-4-sulfonylamino)-propyl 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: 85.0%

1-adamantylzinc bromide + (2R,4S,5R)-4-methyl-5-phenyl-3-(toluene-4-sulfonyl)oxathiazolidine-2-oxide (473554-15-3) → Adamantane-1-sulfinic acid (1R,2S)-1-phenyl-2-(toluene-4-sulfonylamino)-propyl ester (594836-48-3)

Guidance literature:

In tetrahydrofuran; at -78 - -10 ℃;

DOI:10.1016/j.tet.2005.03.122

Reference yield:

N-((1R,2S)-1-hydroxy-1-phenylpropan-2-yl)-4-methylbenzene sulfonamide (108591-33-9) → Adamantane-1-sulfinic acid (1R,2S)-1-phenyl-2-(toluene-4-sulfonylamino)-propyl ester (594836-48-3)

Guidance literature:

Multi-step reaction with 2 steps

1: thionyl chloride; pyridine / tetrahydrofuran / -78 - -45 °C

2: 85 percent / tetrahydrofuran / -78 - -10 °C

With pyridine; thionyl chloride; In tetrahydrofuran;

DOI:10.1016/j.tet.2005.03.122

Reference yield: 91.0%

Adamantane-1-sulfinic acid (1R,2S)-1-phenyl-2-(toluene-4-sulfonylamino)-propyl ester (594836-48-3) + n-butyl magnesium bromide (693-03-8) → (R)-1-adamantyl n-butyl sulfoxide + N-((1R,2S)-1-hydroxy-1-phenylpropan-2-yl)-4-methylbenzene sulfonamide (108591-33-9)

Guidance literature:

In tetrahydrofuran; at -78 - -10 ℃;

DOI:10.1016/j.tet.2005.03.122

upstream raw materials:

(2R,4S,5R)-4-methyl-5-phenyl-3-(toluene-4-sulfonyl)oxathiazolidine-2-oxide

N-((1R,2S)-1-hydroxy-1-phenylpropan-2-yl)-4-methylbenzene sulfonamide

Downstream raw materials:

N-((1R,2S)-1-hydroxy-1-phenylpropan-2-yl)-4-methylbenzene sulfonamide