(S)-methyl-3-([4-allyldimethylsilyl]naphthyl)-2-(tert-butoxycarbamido)propanoate

Base Information

Chemical Name:(S)-methyl-3-([4-allyldimethylsilyl]naphthyl)-2-(tert-butoxycarbamido)propanoate
CAS No.:288372-10-1
Molecular Formula:C₂₀H₃₁NO₄Si
Molecular Weight:377.556
Hs Code.:

Synonyms:(S)-methyl-3-([4-allyldimethylsilyl]naphthyl)-2-(tert-butoxycarbamido)propanoate

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (S)-methyl-3-([4-allyldimethylsilyl]naphthyl)-2-(tert-butoxycarbamido)propanoate

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Technology Process of (S)-methyl-3-([4-allyldimethylsilyl]naphthyl)-2-(tert-butoxycarbamido)propanoate

There total 6 articles about (S)-methyl-3-([4-allyldimethylsilyl]naphthyl)-2-(tert-butoxycarbamido)propanoate 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%

: 24424-99-5
di-tert-butyl dicarbonate

: 288372-09-8
(S)-methyl-2-acetamido-3-([4-allyldimethylsilyl]phenyl)propanoate

: 288372-10-1
(S)-methyl-3-([4-allyldimethylsilyl]naphthyl)-2-(tert-butoxycarbamido)propanoate

Guidance literature:: di-tert-butyl dicarbonate; (S)-methyl-2-acetamido-3-([4-allyldimethylsilyl]phenyl)propanoate; With dmap; In tetrahydrofuran; for 1h; Heating;

With hydrazine hydrate; In methanol; at 20 ℃; for 2h;
DOI:10.1016/S0040-4020(01)00457-4

Reference yield:

: 4028-23-3
Allylchlorodimethylsilane

: 288372-10-1
(S)-methyl-3-([4-allyldimethylsilyl]naphthyl)-2-(tert-butoxycarbamido)propanoate

Guidance literature:: Multi-step reaction with 5 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

1.2: 82 percent / tetrahydrofuran / 1 h / 20 °C

2.1: t-BuLi / tetrahydrofuran; pentane

2.2: 82 percent / 1 h / -78 - 20 °C

3.1: tetramethylguanidine / tetrahydrofuran / 0.25 h / -78 °C

3.2: 86 percent / tetrahydrofuran / -78 - 20 °C

4.1: 100 percent / H₂ / [((S,S)-Et-DuPHOS)-Rh]OTf / CH₂Cl₂ / 23 h / 20 °C / 760 Torr

5.1: DMAP / tetrahydrofuran / 1 h / Heating

5.2: 93 percent / N₂H₄*H₂O / methanol / 2 h / 20 °C

With dmap; n-butyllithium; 1,1,3,3-tetramethylguanidine; hydrogen; tert.-butyl lithium; (+)-1,2-bis((2S,5S)-2,5-diethylphospholano)benzene(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate; In tetrahydrofuran; hexane; dichloromethane; pentane;
DOI:10.1016/S0040-4020(01)00457-4

Reference yield:

: 106-37-6
1.4-dibromobenzene

: 288372-10-1
(S)-methyl-3-([4-allyldimethylsilyl]naphthyl)-2-(tert-butoxycarbamido)propanoate

Guidance literature:: Multi-step reaction with 5 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

1.2: 82 percent / tetrahydrofuran / 1 h / 20 °C

2.1: t-BuLi / tetrahydrofuran; pentane

2.2: 82 percent / 1 h / -78 - 20 °C

3.1: tetramethylguanidine / tetrahydrofuran / 0.25 h / -78 °C

3.2: 86 percent / tetrahydrofuran / -78 - 20 °C

4.1: 100 percent / H₂ / [((S,S)-Et-DuPHOS)-Rh]OTf / CH₂Cl₂ / 23 h / 20 °C / 760 Torr

5.1: DMAP / tetrahydrofuran / 1 h / Heating

5.2: 93 percent / N₂H₄*H₂O / methanol / 2 h / 20 °C

With dmap; n-butyllithium; 1,1,3,3-tetramethylguanidine; hydrogen; tert.-butyl lithium; (+)-1,2-bis((2S,5S)-2,5-diethylphospholano)benzene(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate; In tetrahydrofuran; hexane; dichloromethane; pentane;
DOI:10.1016/S0040-4020(01)00457-4