(2S,3R)-3-Hydroxy-2-hydroxymethyl-4-[1-trimethylsilanyl-meth-(E)-ylidene]-pyrrolidine-1-carboxylic acid phenyl ester

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Chemical Name:(2S,3R)-3-Hydroxy-2-hydroxymethyl-4-[1-trimethylsilanyl-meth-(E)-ylidene]-pyrrolidine-1-carboxylic acid phenyl ester
CAS No.:158470-04-3
Molecular Formula:C₁₆H₂₃NO₄Si
Molecular Weight:321.448
Hs Code.:

Synonyms:(2S,3R)-3-Hydroxy-2-hydroxymethyl-4-[1-trimethylsilanyl-meth-(E)-ylidene]-pyrrolidine-1-carboxylic acid phenyl ester

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Chemical Property of (2S,3R)-3-Hydroxy-2-hydroxymethyl-4-[1-trimethylsilanyl-meth-(E)-ylidene]-pyrrolidine-1-carboxylic acid phenyl ester

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Technology Process of (2S,3R)-3-Hydroxy-2-hydroxymethyl-4-[1-trimethylsilanyl-meth-(E)-ylidene]-pyrrolidine-1-carboxylic acid phenyl ester

There total 6 articles about (2S,3R)-3-Hydroxy-2-hydroxymethyl-4-[1-trimethylsilanyl-meth-(E)-ylidene]-pyrrolidine-1-carboxylic acid phenyl ester 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%

: 158469-98-8
(2S,3R)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-3-hydroxy-4-[1-trimethylsilanyl-meth-(E)-ylidene]-pyrrolidine-1-carboxylic acid phenyl ester

: 158470-04-3
(2S,3R)-3-Hydroxy-2-hydroxymethyl-4-[1-trimethylsilanyl-meth-(E)-ylidene]-pyrrolidine-1-carboxylic acid phenyl ester

Guidance literature:: With toluene-4-sulfonic acid; In methanol; for 0.5h; Ambient temperature;
DOI:10.1016/S0040-4020(01)85517-4

Reference yield:

: 5272-36-6
3-trimethylsilyl-2-propyn-1-ol

: 158470-04-3
(2S,3R)-3-Hydroxy-2-hydroxymethyl-4-[1-trimethylsilanyl-meth-(E)-ylidene]-pyrrolidine-1-carboxylic acid phenyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 43 percent / triphenylphosphine, bromine / dimethylformamide / 18 h / Ambient temperature

2: 20 percent / Et₃N / toluene / 70 deg C, 2 h, then --> room temp., 3 h

3: 96 percent / sat. sodium bicarbonate / ethyl acetate; H₂O / 2 h / 0 °C

4: diisobutylaluminium hydride / toluene / 5 h / -78 °C

5: samarium(II) iodide, tert-butanol / tetrahydrofuran; hexamethylphosphoric acid triamide / 0.25 h / -70 °C

6: 90 percent / p-toluenesulfonic acid / methanol / 0.5 h / Ambient temperature

With samarium diiodide; bromine; diisobutylaluminium hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; triethylamine; triphenylphosphine; tert-butyl alcohol; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; water; ethyl acetate; N,N-dimethyl-formamide; toluene;
DOI:10.1016/S0040-4020(01)85517-4

Reference yield:

: 38002-45-8
3-bromo-1-(trimethylsilyl)-1-propyne

: 158470-04-3
(2S,3R)-3-Hydroxy-2-hydroxymethyl-4-[1-trimethylsilanyl-meth-(E)-ylidene]-pyrrolidine-1-carboxylic acid phenyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 20 percent / Et₃N / toluene / 70 deg C, 2 h, then --> room temp., 3 h

2: 96 percent / sat. sodium bicarbonate / ethyl acetate; H₂O / 2 h / 0 °C

3: diisobutylaluminium hydride / toluene / 5 h / -78 °C

4: samarium(II) iodide, tert-butanol / tetrahydrofuran; hexamethylphosphoric acid triamide / 0.25 h / -70 °C

5: 90 percent / p-toluenesulfonic acid / methanol / 0.5 h / Ambient temperature

With samarium diiodide; diisobutylaluminium hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; triethylamine; tert-butyl alcohol; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; water; ethyl acetate; toluene;
DOI:10.1016/S0040-4020(01)85517-4