mesylate of (+)-(2S,3S,S_S)-(4E)-2-[(tert-butyldimethylsilyl)oxy]-6-methyl-4-(p-tolylsulfinyl)hept-4-en-3-ol

Base Information

• Chemical Name: mesylate of (+)-(2S,3S,S_S)-(4E)-2-[(tert-butyldimethylsilyl)oxy]-6-methyl-4-(p-tolylsulfinyl)hept-4-en-3-ol
• CAS No.: 304881-60-5
• Molecular Formula: C₂₂H₃₈O₅S₂Si
• Molecular Weight: 474.758
• Mol file: 304881-60-5.mol

Synonyms:mesylate of (+)-(2S,3S,S_S)-(4E)-2-[(tert-butyldimethylsilyl)oxy]-6-methyl-4-(p-tolylsulfinyl)hept-4-en-3-ol

Chemical Property of mesylate of (+)-(2S,3S,S_S)-(4E)-2-[(tert-butyldimethylsilyl)oxy]-6-methyl-4-(p-tolylsulfinyl)hept-4-en-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of mesylate of (+)-(2S,3S,S_S)-(4E)-2-[(tert-butyldimethylsilyl)oxy]-6-methyl-4-(p-tolylsulfinyl)hept-4-en-3-ol

There total 3 articles about mesylate of (+)-(2S,3S,S_S)-(4E)-2-[(tert-butyldimethylsilyl)oxy]-6-methyl-4-(p-tolylsulfinyl)hept-4-en-3-ol 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: 75.0%

(+)-(2S,3S,SS)-(4E)-2-[(tert-butyldimethylsilyl)oxy]-6-methyl-4-(p-tolylsulfinyl)hept-4-en-3-ol (184673-47-0) + Methanesulfonic anhydride (7143-01-3) → mesylate of (+)-(2S,3S,SS)-(4E)-2-[(tert-butyldimethylsilyl)oxy]-6-methyl-4-(p-tolylsulfinyl)hept-4-en-3-ol (304881-60-5)

Guidance literature:

With pyridine; at 0 - 20 ℃; for 3h;

DOI:10.1021/jo000468k

Reference yield:

(S)-2-tert-butyl-dimethyl-silanyloxy propanal (87727-28-4) → mesylate of (+)-(2S,3S,SS)-(4E)-2-[(tert-butyldimethylsilyl)oxy]-6-methyl-4-(p-tolylsulfinyl)hept-4-en-3-ol (304881-60-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 70 percent / LDA / tetrahydrofuran / 0.5 h / -78 °C

2: 75 percent / pyridine / 3 h / 0 - 20 °C

With pyridine; lithium diisopropyl amide; In tetrahydrofuran; 1: Addition / 2: Condensation;

DOI:10.1021/jo000468k

Reference yield:

1-Methyl-4-((S)-(E)-3-methyl-but-1-ene-1-sulfinyl)-benzene → mesylate of (+)-(2S,3S,SS)-(4E)-2-[(tert-butyldimethylsilyl)oxy]-6-methyl-4-(p-tolylsulfinyl)hept-4-en-3-ol (304881-60-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 70 percent / LDA / tetrahydrofuran / 0.5 h / -78 °C

2: 75 percent / pyridine / 3 h / 0 - 20 °C

With pyridine; lithium diisopropyl amide; In tetrahydrofuran; 1: Addition / 2: Condensation;

DOI:10.1021/jo000468k

upstream raw materials:

(+)-(2S,3S,S_S)-(4E)-2-[(tert-butyldimethylsilyl)oxy]-6-methyl-4-(p-tolylsulfinyl)hept-4-en-3-ol

Methanesulfonic anhydride

(S)-2-tert-butyl-dimethyl-silanyloxy propanal

Downstream raw materials:

(+)-(2S,3R,S_S)-(4E)-2,3-epoxy-6-methyl-4-(p-tolylsulfinyl)hept-4-ene