5(S),3(S)-3-benzyl-4-tert-butoxycarbonyl-1-(2,4-dimethoxybenzyl)-5-[2-(phenylsulfonyloxy)ethyl]-2-piperazinone

Base Information

Chemical Name:5(S),3(S)-3-benzyl-4-tert-butoxycarbonyl-1-(2,4-dimethoxybenzyl)-5-[2-(phenylsulfonyloxy)ethyl]-2-piperazinone
CAS No.:335160-81-1
Molecular Formula:C₃₃H₄₀N₂O₈S
Molecular Weight:624.755
Hs Code.:

Synonyms:5(S),3(S)-3-benzyl-4-tert-butoxycarbonyl-1-(2,4-dimethoxybenzyl)-5-[2-(phenylsulfonyloxy)ethyl]-2-piperazinone

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Chemical Property of 5(S),3(S)-3-benzyl-4-tert-butoxycarbonyl-1-(2,4-dimethoxybenzyl)-5-[2-(phenylsulfonyloxy)ethyl]-2-piperazinone

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Technology Process of 5(S),3(S)-3-benzyl-4-tert-butoxycarbonyl-1-(2,4-dimethoxybenzyl)-5-[2-(phenylsulfonyloxy)ethyl]-2-piperazinone

There total 10 articles about 5(S),3(S)-3-benzyl-4-tert-butoxycarbonyl-1-(2,4-dimethoxybenzyl)-5-[2-(phenylsulfonyloxy)ethyl]-2-piperazinone 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%

: 98-09-9
benzenesulfonyl chloride

: 335160-79-7
5(S),3(S)-3-benzyl-4-tert-butoxycarbonyl-1-(2,4-dimethoxybenzyl)-5-(2-hydroxyethyl)-2-piperazinone

: 335160-81-1
5(S),3(S)-3-benzyl-4-tert-butoxycarbonyl-1-(2,4-dimethoxybenzyl)-5-[2-(phenylsulfonyloxy)ethyl]-2-piperazinone

Guidance literature:: With triethylamine; In dichloromethane; at 20 ℃; for 1h;
DOI:10.1021/ol015504w

Reference yield:

: 5(S)-5-allyl-3-benzyl-4-tert-butoxycarbonyl-1-(2,4-dimethoxybenzyl)-2-piperazinone

: 335160-81-1
5(S),3(S)-3-benzyl-4-tert-butoxycarbonyl-1-(2,4-dimethoxybenzyl)-5-[2-(phenylsulfonyloxy)ethyl]-2-piperazinone

Guidance literature:: Multi-step reaction with 3 steps

1.1: OsO₄; NMO / 2-methyl-propan-2-ol; tetrahydrofuran; H₂O / 2.5 h

1.2: NaIO₄; NaHCO₃ / H₂O; 2-methyl-propan-2-ol; tetrahydrofuran / 2 h

2.1: 70 percent / NaBH₄ / ethanol / 0.33 h / 0 °C

3.1: 90 percent / Et₃N / CH₂Cl₂ / 1 h / 20 °C

With sodium tetrahydroborate; osmium(VIII) oxide; N-methyl-2-indolinone; triethylamine; In tetrahydrofuran; ethanol; dichloromethane; water; tert-butyl alcohol;
DOI:10.1021/ol015504w

Reference yield:

: 20781-21-9
2,4-dimethoxybenzylamine hydrochloride

: 335160-81-1
5(S),3(S)-3-benzyl-4-tert-butoxycarbonyl-1-(2,4-dimethoxybenzyl)-5-[2-(phenylsulfonyloxy)ethyl]-2-piperazinone

Guidance literature:: Multi-step reaction with 7 steps

1.1: 90 percent / Na(AcO)3BH; 4 Angstroem molecular sieves / 1,2-dichloro-ethane / 14 h / 20 °C

2.1: 93 percent / NaHCO₃ / ethyl acetate; H₂O / 0.33 h / 0 °C

3.1: 75 percent / Cs₂CO₃ / dimethylformamide / 2 h / 65 °C

4.1: LiHMDS / tetrahydrofuran / 3.5 h / -78 °C

5.1: OsO₄; NMO / 2-methyl-propan-2-ol; tetrahydrofuran; H₂O / 2.5 h

5.2: NaIO₄; NaHCO₃ / H₂O; 2-methyl-propan-2-ol; tetrahydrofuran / 2 h

6.1: 70 percent / NaBH₄ / ethanol / 0.33 h / 0 °C

7.1: 90 percent / Et₃N / CH₂Cl₂ / 1 h / 20 °C

With sodium tetrahydroborate; osmium(VIII) oxide; N-methyl-2-indolinone; 4 A molecular sieve; sodium tris(acetoxy)borohydride; sodium hydrogencarbonate; caesium carbonate; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; ethanol; dichloromethane; water; ethyl acetate; 1,2-dichloro-ethane; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1021/ol015504w