(3S,4R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-4-ethyl-3-hydroxy-1-(toluene-4-sulfonyl)-pyrrolidin-2-one

Base Information

Chemical Name:(3S,4R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-4-ethyl-3-hydroxy-1-(toluene-4-sulfonyl)-pyrrolidin-2-one
CAS No.:132974-87-9
Molecular Formula:C₃₀H₃₇NO₅SSi
Molecular Weight:551.779
Hs Code.:

Synonyms:(3S,4R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-4-ethyl-3-hydroxy-1-(toluene-4-sulfonyl)-pyrrolidin-2-one

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Chemical Property of (3S,4R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-4-ethyl-3-hydroxy-1-(toluene-4-sulfonyl)-pyrrolidin-2-one

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Technology Process of (3S,4R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-4-ethyl-3-hydroxy-1-(toluene-4-sulfonyl)-pyrrolidin-2-one

There total 8 articles about (3S,4R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-4-ethyl-3-hydroxy-1-(toluene-4-sulfonyl)-pyrrolidin-2-one 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:

: 17342-08-4
(S)-Pyroglutaminol

: 132974-87-9
(3S,4R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-4-ethyl-3-hydroxy-1-(toluene-4-sulfonyl)-pyrrolidin-2-one

Guidance literature:: Multi-step reaction with 6 steps

1: 81 percent / Et₃N, DMAP / CH₂Cl₂

2: 1) LiHMDS / 1) THF, -20 deg C, 10 min

3: 1) LiHMDS / 1) THF, -20 deg C, 20 min

4: H₂O₂ / tetrahydrofuran; H₂O

5: 75 percent / diethyl ether / -78 °C

6: 1) NaHMDS 2) trans-2-(phenylsulfonyl)-3-phenyloxaziridine / 1) THF, -78 deg C, 15 min

With dmap; dihydrogen peroxide; sodium hexamethyldisilazane; N-(benzenesulfonyl)-3-phenyloxaziridine; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; dichloromethane; water;
DOI:10.1016/0040-4039(91)80876-8

Reference yield:

: 132974-83-5
(5S)-5-[[(tert-butyldiphenylsilyl)oxy]methyl]pyrrolidin-2-one

: 132974-87-9
(3S,4R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-4-ethyl-3-hydroxy-1-(toluene-4-sulfonyl)-pyrrolidin-2-one

Guidance literature:: Multi-step reaction with 5 steps

1: 1) LiHMDS / 1) THF, -20 deg C, 10 min

2: 1) LiHMDS / 1) THF, -20 deg C, 20 min

3: H₂O₂ / tetrahydrofuran; H₂O

4: 75 percent / diethyl ether / -78 °C

5: 1) NaHMDS 2) trans-2-(phenylsulfonyl)-3-phenyloxaziridine / 1) THF, -78 deg C, 15 min

With dihydrogen peroxide; sodium hexamethyldisilazane; N-(benzenesulfonyl)-3-phenyloxaziridine; lithium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; water;
DOI:10.1016/0040-4039(91)80876-8

Reference yield:

: 132974-85-7
(-)-(5S)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-1-tosyl-1,5-dihydro-2H-pyrrol-2-one

: 132974-87-9
(3S,4R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-4-ethyl-3-hydroxy-1-(toluene-4-sulfonyl)-pyrrolidin-2-one

Guidance literature:: Multi-step reaction with 2 steps

1: 75 percent / diethyl ether / -78 °C

2: 1) NaHMDS 2) trans-2-(phenylsulfonyl)-3-phenyloxaziridine / 1) THF, -78 deg C, 15 min

With sodium hexamethyldisilazane; N-(benzenesulfonyl)-3-phenyloxaziridine; In diethyl ether;
DOI:10.1016/0040-4039(91)80876-8