(2S,3S,4R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-4-ethyl-1-(toluene-4-sulfonyl)-pyrrolidine-2,3-diol

Base Information

Chemical Name:(2S,3S,4R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-4-ethyl-1-(toluene-4-sulfonyl)-pyrrolidine-2,3-diol
CAS No.:132974-92-6
Molecular Formula:C₃₀H₃₉NO₅SSi
Molecular Weight:553.795
Hs Code.:

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

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

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

There total 9 articles about (2S,3S,4R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-4-ethyl-1-(toluene-4-sulfonyl)-pyrrolidine-2,3-diol 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: 90.0%

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

: 132974-92-6
(2S,3S,4R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-4-ethyl-1-(toluene-4-sulfonyl)-pyrrolidine-2,3-diol

Guidance literature:: With diisobutylaluminium hydride; In dichloromethane; -78 deg C to r.t.; or LiAlH₄, THF, 0 deg C to reflux;
DOI:10.1016/0040-4039(91)80876-8

Reference yield:

: 17342-08-4
(S)-Pyroglutaminol

: 132974-92-6
(2S,3S,4R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-4-ethyl-1-(toluene-4-sulfonyl)-pyrrolidine-2,3-diol

Guidance literature:: Multi-step reaction with 7 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

7: 90 percent / DIBAL / CH₂Cl₂ / -78 deg C to r.t.; or LiAlH₄, THF, 0 deg C to reflux

With dmap; dihydrogen peroxide; sodium hexamethyldisilazane; diisobutylaluminium hydride; 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

: 132974-92-6
(2S,3S,4R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-4-ethyl-1-(toluene-4-sulfonyl)-pyrrolidine-2,3-diol

Guidance literature:: Multi-step reaction with 6 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

6: 90 percent / DIBAL / CH₂Cl₂ / -78 deg C to r.t.; or LiAlH₄, THF, 0 deg C to reflux

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