(2S,3R)-3-(benzyloxy)methyl-1-(4-methylphenyl)sulfonyl-2-aziridinemethanol

Base Information

• Chemical Name: (2S,3R)-3-(benzyloxy)methyl-1-(4-methylphenyl)sulfonyl-2-aziridinemethanol
• CAS No.: 167254-91-3
• Molecular Formula: C₁₈H₂₁NO₄S
• Molecular Weight: 347.435
• Mol file: 167254-91-3.mol

Synonyms:(2S,3R)-3-(benzyloxy)methyl-1-(4-methylphenyl)sulfonyl-2-aziridinemethanol

Chemical Property of (2S,3R)-3-(benzyloxy)methyl-1-(4-methylphenyl)sulfonyl-2-aziridinemethanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R)-3-(benzyloxy)methyl-1-(4-methylphenyl)sulfonyl-2-aziridinemethanol

There total 3 articles about (2S,3R)-3-(benzyloxy)methyl-1-(4-methylphenyl)sulfonyl-2-aziridinemethanol 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: 88.0%

C19H20BrNO5S (1433956-44-5) → (2S,3R)-3-(benzyloxy)methyl-1-(4-methylphenyl)sulfonyl-2-aziridinemethanol (167254-91-3)

Guidance literature:

C₁₉H₂₀BrNO₅S; With potassium carbonate; In methanol; at 20 ℃;

With hydrogenchloride; In methanol; water; at 20 ℃;

DOI:10.1021/ja4010877

Reference yield: 74.4%

(2S,3R)-3-(benzyloxy)methyl-2-(tert-butyldimethylsiloxy)methyl-1-<(4-methylphenyl)sulfonyl>aziridine (167613-41-4) → (2S,3R)-3-(benzyloxy)methyl-1-(4-methylphenyl)sulfonyl-2-aziridinemethanol (167254-91-3)

Guidance literature:

With n-BuNF; In tetrahydrofuran; at 0 ℃; for 0.5h;

DOI:10.1248/cpb.42.2241

Reference yield:

C19H21NO5S (1433956-63-8) → (2S,3R)-3-(benzyloxy)methyl-1-(4-methylphenyl)sulfonyl-2-aziridinemethanol (167254-91-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: N-Bromosuccinimide; scandium tris(trifluoromethanesulfonate); (1R,2R)-1,2-bis[(2-diphenylphosphanyl)benzoylamino]cyclohexane / dichloromethane; toluene / 72 h / -50 °C

2.1: potassium carbonate / methanol / 20 °C

2.2: 20 °C

With N-Bromosuccinimide; potassium carbonate; (1R,2R)-1,2-bis[(2-diphenylphosphanyl)benzoylamino]cyclohexane; scandium tris(trifluoromethanesulfonate); In methanol; dichloromethane; toluene;

DOI:10.1021/ja4010877

upstream raw materials:

(2S,3R)-3-(benzyloxy)methyl-2-(tert-butyldimethylsiloxy)methyl-1-<(4-methylphenyl)sulfonyl>aziridine

C₁₉H₂₁NO₅S

C₁₉H₂₀BrNO₅S

Downstream raw materials:

N-((S)-3-Benzyloxy-1-hydroxymethyl-propyl)-4-methyl-benzenesulfonamide

(2S)-N-(1-benzyloxymethyl-3-hydroxypropyl)-4-methylbenzenesulfonamide

(2S,3S)-1-benzyloxy-2-(4-methylphenyl)sulfonylamino-3-octadecanol