(2S,3R,4S)-5-(tert-Butyl-diphenyl-silanyloxy)-3-ethyl-2-hydroxy-4-(toluene-4-sulfonylamino)-pentanoic acid

Base Information

Chemical Name:(2S,3R,4S)-5-(tert-Butyl-diphenyl-silanyloxy)-3-ethyl-2-hydroxy-4-(toluene-4-sulfonylamino)-pentanoic acid
CAS No.:132974-88-0
Molecular Formula:C₃₀H₃₉NO₆SSi
Molecular Weight:569.794
Hs Code.:

Synonyms:(2S,3R,4S)-5-(tert-Butyl-diphenyl-silanyloxy)-3-ethyl-2-hydroxy-4-(toluene-4-sulfonylamino)-pentanoic acid

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Chemical Property of (2S,3R,4S)-5-(tert-Butyl-diphenyl-silanyloxy)-3-ethyl-2-hydroxy-4-(toluene-4-sulfonylamino)-pentanoic acid

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Technology Process of (2S,3R,4S)-5-(tert-Butyl-diphenyl-silanyloxy)-3-ethyl-2-hydroxy-4-(toluene-4-sulfonylamino)-pentanoic acid

There total 9 articles about (2S,3R,4S)-5-(tert-Butyl-diphenyl-silanyloxy)-3-ethyl-2-hydroxy-4-(toluene-4-sulfonylamino)-pentanoic acid 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

: 132974-88-0
(2S,3R,4S)-5-(tert-Butyl-diphenyl-silanyloxy)-3-ethyl-2-hydroxy-4-(toluene-4-sulfonylamino)-pentanoic acid

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: LiOH / tetrahydrofuran; H₂O / 0 deg C to r.t.

With dmap; lithium hydroxide; 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:

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

: 132974-88-0
(2S,3R,4S)-5-(tert-Butyl-diphenyl-silanyloxy)-3-ethyl-2-hydroxy-4-(toluene-4-sulfonylamino)-pentanoic acid

Guidance literature:: With lithium hydroxide; In tetrahydrofuran; water; 0 deg C to r.t.;
DOI:10.1016/0040-4039(91)80876-8

Reference yield:

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

: 132974-88-0
(2S,3R,4S)-5-(tert-Butyl-diphenyl-silanyloxy)-3-ethyl-2-hydroxy-4-(toluene-4-sulfonylamino)-pentanoic acid

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: LiOH / tetrahydrofuran; H₂O / 0 deg C to r.t.

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