2-(p-Tolylsulfonyl)ethyl 5-<(tert-Butyldimethylsilyl)oxy>-3-methyl-2(S),3(R)-epoxypentanoate

Base Information

Chemical Name:2-(p-Tolylsulfonyl)ethyl 5-<(tert-Butyldimethylsilyl)oxy>-3-methyl-2(S),3(R)-epoxypentanoate
CAS No.:92220-09-2
Molecular Formula:C₂₁H₃₄O₆SSi
Molecular Weight:442.649
Hs Code.:

Synonyms:2-(p-Tolylsulfonyl)ethyl 5-<(tert-Butyldimethylsilyl)oxy>-3-methyl-2(S),3(R)-epoxypentanoate

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Chemical Property of 2-(p-Tolylsulfonyl)ethyl 5-<(tert-Butyldimethylsilyl)oxy>-3-methyl-2(S),3(R)-epoxypentanoate

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Technology Process of 2-(p-Tolylsulfonyl)ethyl 5-<(tert-Butyldimethylsilyl)oxy>-3-methyl-2(S),3(R)-epoxypentanoate

There total 6 articles about 2-(p-Tolylsulfonyl)ethyl 5-<(tert-Butyldimethylsilyl)oxy>-3-methyl-2(S),3(R)-epoxypentanoate 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: 56.0%

: 22381-54-0
2-(p-tolylsulfonyl)ethanol

: 92220-19-4
(2S,3R)-3-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-methyl-oxirane-2-carboxylic acid

: 92220-09-2
2-(p-Tolylsulfonyl)ethyl 5-<(tert-Butyldimethylsilyl)oxy>-3-methyl-2(S),3(R)-epoxypentanoate

Guidance literature:: With dmap; N,N-bis[2-oxo-3-oxazolidinyl]phosphorodiamidic chloride; triethylamine; In dichloromethane; at 25 ℃; for 16h;
DOI:10.1021/jo00197a002

Reference yield:

: 35066-36-5
5-hydroxy-3-methyl-2-(E)-pentenoic acid methyl ester

: 92220-09-2
2-(p-Tolylsulfonyl)ethyl 5-<(tert-Butyldimethylsilyl)oxy>-3-methyl-2(S),3(R)-epoxypentanoate

Guidance literature:: Multi-step reaction with 5 steps

1: imidazole / dimethylformamide / 13 h / 25 °C

2: Dibal-H (1 M hexane solution) / diethyl ether / 1) -78 deg C, 10 min, 2) 25 deg C, 1.5 h

3: 81 percent / (-)-diethyl tartrate, titanium(IV)isopropoxide, tert-butyl hydroperoxide (3.98 M toluene solution) / CH₂Cl₂ / 17 h / -20 °C

4: KMnO₄, Bu₄NBr / H₂O; benzene / 28 h / 25 °C

5: 56 percent / triethylamine, N,N-bis<2-oxo-3-oxazolidinyl>phosphorodiamidic chloride, 4-(dimethylamino)pyridine / CH₂Cl₂ / 16 h / 25 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; potassium permanganate; N,N-bis[2-oxo-3-oxazolidinyl]phosphorodiamidic chloride; tetrabutylammomium bromide; diisobutylaluminium hydride; (-)-diethyl tartrate; triethylamine; In diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; benzene;
DOI:10.1021/jo00197a002

Reference yield:

: 90708-82-0
5-<(tert-Butyldimethylsilyl)oxy>-3-methyl-2(E)-penten-1-ol

: 92220-09-2
2-(p-Tolylsulfonyl)ethyl 5-<(tert-Butyldimethylsilyl)oxy>-3-methyl-2(S),3(R)-epoxypentanoate

Guidance literature:: Multi-step reaction with 3 steps

1: 81 percent / (-)-diethyl tartrate, titanium(IV)isopropoxide, tert-butyl hydroperoxide (3.98 M toluene solution) / CH₂Cl₂ / 17 h / -20 °C

2: KMnO₄, Bu₄NBr / H₂O; benzene / 28 h / 25 °C

3: 56 percent / triethylamine, N,N-bis<2-oxo-3-oxazolidinyl>phosphorodiamidic chloride, 4-(dimethylamino)pyridine / CH₂Cl₂ / 16 h / 25 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; potassium permanganate; N,N-bis[2-oxo-3-oxazolidinyl]phosphorodiamidic chloride; tetrabutylammomium bromide; (-)-diethyl tartrate; triethylamine; In dichloromethane; water; benzene;
DOI:10.1021/jo00197a002