(2S,9R)-9-(tert-butyldiphenylsiloxy)-8-oxo-2-(tert-butoxycarbonyl)-amino-4-decenoic acid benzyl ester

Base Information

Chemical Name:(2S,9R)-9-(tert-butyldiphenylsiloxy)-8-oxo-2-(tert-butoxycarbonyl)-amino-4-decenoic acid benzyl ester
CAS No.:857478-17-2
Molecular Formula:C₃₈H₄₉NO₆Si
Molecular Weight:643.896
Hs Code.:

Synonyms:(2S,9R)-9-(tert-butyldiphenylsiloxy)-8-oxo-2-(tert-butoxycarbonyl)-amino-4-decenoic acid benzyl ester

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Chemical Property of (2S,9R)-9-(tert-butyldiphenylsiloxy)-8-oxo-2-(tert-butoxycarbonyl)-amino-4-decenoic acid benzyl ester

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Technology Process of (2S,9R)-9-(tert-butyldiphenylsiloxy)-8-oxo-2-(tert-butoxycarbonyl)-amino-4-decenoic acid benzyl ester

There total 4 articles about (2S,9R)-9-(tert-butyldiphenylsiloxy)-8-oxo-2-(tert-butoxycarbonyl)-amino-4-decenoic acid benzyl 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:

: 561038-05-9
(R)-2-(tert-butyldiphenylsilanyloxy)propionic acid methyl ester

: 857478-17-2
(2S,9R)-9-(tert-butyldiphenylsiloxy)-8-oxo-2-(tert-butoxycarbonyl)-amino-4-decenoic acid benzyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: LiOH / tetrahydrofuran; H₂O

2.1: 2.91 g / EDC; DIPEA / CH₂Cl₂

3.1: Mg

3.2: 89 percent / tetrahydrofuran / 3 h / 20 °C

4.1: 55 percent / second-generation Grubbs RCM catalyst / 1,2-dichloro-ethane / 168 h / 20 °C

With lithium hydroxide; magnesium; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; dichloromethane; water; 1,2-dichloro-ethane; 3.2: Grignard reaction;
DOI:10.1021/ol050991r

Reference yield:

: 857478-12-7
(2R)-N-methoxy-N-methyl-2-(t-butyldiphenylsilyloxy)propanamide

: 857478-17-2
(2S,9R)-9-(tert-butyldiphenylsiloxy)-8-oxo-2-(tert-butoxycarbonyl)-amino-4-decenoic acid benzyl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: Mg

1.2: 89 percent / tetrahydrofuran / 3 h / 20 °C

2.1: 55 percent / second-generation Grubbs RCM catalyst / 1,2-dichloro-ethane / 168 h / 20 °C

With magnesium; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In 1,2-dichloro-ethane; 1.2: Grignard reaction;
DOI:10.1021/ol050991r

Reference yield:

: 110407-68-6
(R)-2-((tert-butyldiphenylsilyl)oxy)propanoic acid

: 857478-17-2
(2S,9R)-9-(tert-butyldiphenylsiloxy)-8-oxo-2-(tert-butoxycarbonyl)-amino-4-decenoic acid benzyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: 2.91 g / EDC; DIPEA / CH₂Cl₂

2.1: Mg

2.2: 89 percent / tetrahydrofuran / 3 h / 20 °C

3.1: 55 percent / second-generation Grubbs RCM catalyst / 1,2-dichloro-ethane / 168 h / 20 °C

With magnesium; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In dichloromethane; 1,2-dichloro-ethane; 2.2: Grignard reaction;
DOI:10.1021/ol050991r