1(S),5(S)-1-benzyl-8-tert-butoxycarbonyl-3-(2,4-dimethoxybenzyl)-3,8-diaza-2-oxobicyclo[3.2.1]octane

Base Information

Chemical Name:1(S),5(S)-1-benzyl-8-tert-butoxycarbonyl-3-(2,4-dimethoxybenzyl)-3,8-diaza-2-oxobicyclo[3.2.1]octane
CAS No.:335160-83-3
Molecular Formula:C₂₇H₃₄N₂O₅
Molecular Weight:466.577
Hs Code.:

Synonyms:1(S),5(S)-1-benzyl-8-tert-butoxycarbonyl-3-(2,4-dimethoxybenzyl)-3,8-diaza-2-oxobicyclo[3.2.1]octane

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Chemical Property of 1(S),5(S)-1-benzyl-8-tert-butoxycarbonyl-3-(2,4-dimethoxybenzyl)-3,8-diaza-2-oxobicyclo[3.2.1]octane

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Technology Process of 1(S),5(S)-1-benzyl-8-tert-butoxycarbonyl-3-(2,4-dimethoxybenzyl)-3,8-diaza-2-oxobicyclo[3.2.1]octane

There total 11 articles about 1(S),5(S)-1-benzyl-8-tert-butoxycarbonyl-3-(2,4-dimethoxybenzyl)-3,8-diaza-2-oxobicyclo[3.2.1]octane 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: 63.0%

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

: 335160-83-3
1(S),5(S)-1-benzyl-8-tert-butoxycarbonyl-3-(2,4-dimethoxybenzyl)-3,8-diaza-2-oxobicyclo[3.2.1]octane

Guidance literature:: With lithium diisopropyl amide; In tetrahydrofuran; at -78 - 0 ℃;
DOI:10.1021/ol015504w

Reference yield:

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

: 335160-83-3
1(S),5(S)-1-benzyl-8-tert-butoxycarbonyl-3-(2,4-dimethoxybenzyl)-3,8-diaza-2-oxobicyclo[3.2.1]octane

Guidance literature:: Multi-step reaction with 4 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

4.1: 63 percent / LDA / tetrahydrofuran / -78 - 0 °C

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

Reference yield:

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

: 335160-83-3
1(S),5(S)-1-benzyl-8-tert-butoxycarbonyl-3-(2,4-dimethoxybenzyl)-3,8-diaza-2-oxobicyclo[3.2.1]octane

Guidance literature:: Multi-step reaction with 8 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

8.1: 63 percent / LDA / tetrahydrofuran / -78 - 0 °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; lithium diisopropyl amide; In tetrahydrofuran; ethanol; dichloromethane; water; ethyl acetate; 1,2-dichloro-ethane; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1021/ol015504w