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

Base Information

• Chemical Name: mesylate of (+)-(2S,3S,S_S)-(4E)-3-[(tert-butyldimethylsilyl)oxy]-6-methyl-4-(p-tolylsulfinyl)hept-4-en-2-ol
• CAS No.: 304881-64-9
• Molecular Formula: C₂₂H₃₈O₅S₂Si
• Molecular Weight: 474.758

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

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

Chemical Property:

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

There total 1 articles about mesylate of (+)-(2S,3S,S_S)-(4E)-3-[(tert-butyldimethylsilyl)oxy]-6-methyl-4-(p-tolylsulfinyl)hept-4-en-2-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:

(+)-(2S,3S,SS)-(4E)-3-[(tert-butyldimethylsilyl)oxy]-6-methyl-4-(p-tolylsulfinyl)hept-4-en-2-ol (304881-44-5) + Methanesulfonic anhydride (7143-01-3) → mesylate of (+)-(2S,3S,SS)-(4E)-3-[(tert-butyldimethylsilyl)oxy]-6-methyl-4-(p-tolylsulfinyl)hept-4-en-2-ol (304881-64-9)

Guidance literature:

With pyridine; at 0 - 20 ℃; for 3h;

DOI:10.1021/jo000468k

Reference yield:

mesylate of (+)-(2S,3S,SS)-(4E)-3-[(tert-butyldimethylsilyl)oxy]-6-methyl-4-(p-tolylsulfinyl)hept-4-en-2-ol (304881-64-9) → (+)-(2R,3S,SS)-(4E)-2,3-epoxy-6-methyl-4-(p-tolylsulfinyl)hept-4-ene (304881-65-0)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 0.0833333h;

DOI:10.1021/jo000468k

Reference yield:

mesylate of (+)-(2S,3S,SS)-(4E)-3-[(tert-butyldimethylsilyl)oxy]-6-methyl-4-(p-tolylsulfinyl)hept-4-en-2-ol (304881-64-9) → (2R,5R,SS)-(3Z)-5-ethyl-6-methyl-4-(p-tolylsulfinyl)hept-3-en-2-ol

Guidance literature:

Multi-step reaction with 2 steps

1: 77 mg / n-Bu₄NF / tetrahydrofuran / 0.08 h / 20 °C

2: 38 percent / diethyl ether / -78 - 20 °C

With tetrabutyl ammonium fluoride; In tetrahydrofuran; diethyl ether; 1: Elimination / 2: Addition;

DOI:10.1021/jo000468k

upstream raw materials:

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

Methanesulfonic anhydride

Downstream raw materials:

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

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

(-)-(2R,5R,S_S)-(3Z)-5-isopropyl-4-(p-tolylsulfinyl)non-3-en-2-ol

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