(2S,9R)-9-(tert-butyldiphenylsiloxy)-8-oxo-2-(tert-butoxycarbonyl)amino-decanoic acid

Base Information

Chemical Name:(2S,9R)-9-(tert-butyldiphenylsiloxy)-8-oxo-2-(tert-butoxycarbonyl)amino-decanoic acid
CAS No.:857478-19-4
Molecular Formula:C₃₁H₄₅NO₆Si
Molecular Weight:555.787
Hs Code.:

Synonyms:(2S,9R)-9-(tert-butyldiphenylsiloxy)-8-oxo-2-(tert-butoxycarbonyl)amino-decanoic acid

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Chemical Property of (2S,9R)-9-(tert-butyldiphenylsiloxy)-8-oxo-2-(tert-butoxycarbonyl)amino-decanoic acid

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Technology Process of (2S,9R)-9-(tert-butyldiphenylsiloxy)-8-oxo-2-(tert-butoxycarbonyl)amino-decanoic acid

There total 6 articles about (2S,9R)-9-(tert-butyldiphenylsiloxy)-8-oxo-2-(tert-butoxycarbonyl)amino-decanoic acid 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: 94.0%

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

: 857478-19-4
(2S,9R)-9-(tert-butyldiphenylsiloxy)-8-oxo-2-(tert-butoxycarbonyl)amino-decanoic acid

Guidance literature:: With hydrogen; palladium on activated charcoal; In methanol; for 6h; under 760 Torr;
DOI:10.1021/ol050991r

Reference yield:

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

: 857478-19-4
(2S,9R)-9-(tert-butyldiphenylsiloxy)-8-oxo-2-(tert-butoxycarbonyl)amino-decanoic acid

Guidance literature:: Multi-step reaction with 5 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

5.1: 94 percent / H₂ / Pd/C / methanol / 6 h / 760 Torr

With lithium hydroxide; hydrogen; 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; palladium on activated charcoal; In tetrahydrofuran; methanol; 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

: 857478-19-4
(2S,9R)-9-(tert-butyldiphenylsiloxy)-8-oxo-2-(tert-butoxycarbonyl)amino-decanoic acid

Guidance literature:: Multi-step reaction with 3 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

3.1: 94 percent / H₂ / Pd/C / methanol / 6 h / 760 Torr

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