t-butyl (2S,3S,4RS)-1-t-butoxycarbonyl-3-methyl-4-phenylselenopyroglutamate

Base Information

Chemical Name:t-butyl (2S,3S,4RS)-1-t-butoxycarbonyl-3-methyl-4-phenylselenopyroglutamate
CAS No.:331747-59-2
Molecular Formula:C₂₁H₂₉NO₅Se
Molecular Weight:454.425
Hs Code.:

Synonyms:t-butyl (2S,3S,4RS)-1-t-butoxycarbonyl-3-methyl-4-phenylselenopyroglutamate

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Chemical Property of t-butyl (2S,3S,4RS)-1-t-butoxycarbonyl-3-methyl-4-phenylselenopyroglutamate

Chemical Property:

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Technology Process of t-butyl (2S,3S,4RS)-1-t-butoxycarbonyl-3-methyl-4-phenylselenopyroglutamate

There total 5 articles about t-butyl (2S,3S,4RS)-1-t-butoxycarbonyl-3-methyl-4-phenylselenopyroglutamate 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: 93.0%

: 5707-04-0
Phenylselenyl chloride

: 331747-58-1
t-butyl (2S,3S)-1-t-butoxycarbonyl-3-methylpyroglutamate

: 331747-59-2
t-butyl (2S,3S,4RS)-1-t-butoxycarbonyl-3-methyl-4-phenylselenopyroglutamate

Guidance literature:: t-butyl (2S,3S)-1-t-butoxycarbonyl-3-methylpyroglutamate; With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; sodium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 0.5h;

Phenylselenyl chloride; In tetrahydrofuran; at -78 ℃; for 2h;
DOI:10.1002/jlcr.439

Reference yield:

: 81658-27-7
(S)-tert-butyl 2-(((tert-butyldimethylsilyl)oxy)methyl)-5-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate

: 331747-59-2
t-butyl (2S,3S,4RS)-1-t-butoxycarbonyl-3-methyl-4-phenylselenopyroglutamate

Guidance literature:: Multi-step reaction with 5 steps

1.1: CuI / diethyl ether / 0.17 h / -15 °C

1.2: 1.60 g / diethyl ether / 4 h / -78 °C

2.1: 90 percent / p-toluenesulfonic acid / methanol / 20 °C

3.1: 953 mg / NaIO₄; RuCl₃*nH₂O / H₂O; acetone / 1 h / 20 °C

4.1: 51 percent / N,N-dimethylformamide dineopentyl acetal / benzene / 0.5 h / Heating

5.1: NaHMDS; DMPU / tetrahydrofuran / 0.5 h / -78 °C

5.2: 93 percent / tetrahydrofuran / 2 h / -78 °C

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; ruthenium trichloride; sodium periodate; copper(l) iodide; sodium hexamethyldisilazane; toluene-4-sulfonic acid; N,N-dimethylformamide dineopentyl acetal; In tetrahydrofuran; methanol; diethyl ether; water; acetone; benzene;
DOI:10.1002/jlcr.439

Reference yield:

: 149053-03-2
(4S,5S)-1-t-butoxycarbonyl-5-t-butyldimethylsiloxymethyl-4-methyl-2-pyrrolidone

: 331747-59-2
t-butyl (2S,3S,4RS)-1-t-butoxycarbonyl-3-methyl-4-phenylselenopyroglutamate

Guidance literature:: Multi-step reaction with 4 steps

1.1: 90 percent / p-toluenesulfonic acid / methanol / 20 °C

2.1: 953 mg / NaIO₄; RuCl₃*nH₂O / H₂O; acetone / 1 h / 20 °C

3.1: 51 percent / N,N-dimethylformamide dineopentyl acetal / benzene / 0.5 h / Heating

4.1: NaHMDS; DMPU / tetrahydrofuran / 0.5 h / -78 °C

4.2: 93 percent / tetrahydrofuran / 2 h / -78 °C

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; ruthenium trichloride; sodium periodate; sodium hexamethyldisilazane; toluene-4-sulfonic acid; N,N-dimethylformamide dineopentyl acetal; In tetrahydrofuran; methanol; water; acetone; benzene;
DOI:10.1002/jlcr.439