(2S,3S)-1-((R)-1-(allyloxy)-14-methyl-1-oxopentadecan-3-yl)-4-cyclohexyl-3-(benzyloxy)-2-(tert-butoxycarbonylamino)succinate

Base Information

Chemical Name:(2S,3S)-1-((R)-1-(allyloxy)-14-methyl-1-oxopentadecan-3-yl)-4-cyclohexyl-3-(benzyloxy)-2-(tert-butoxycarbonylamino)succinate
CAS No.:936703-49-0
Molecular Formula:C₄₁H₆₅NO₉
Molecular Weight:715.968
Hs Code.:

Synonyms:(2S,3S)-1-((R)-1-(allyloxy)-14-methyl-1-oxopentadecan-3-yl)-4-cyclohexyl-3-(benzyloxy)-2-(tert-butoxycarbonylamino)succinate

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Chemical Property of (2S,3S)-1-((R)-1-(allyloxy)-14-methyl-1-oxopentadecan-3-yl)-4-cyclohexyl-3-(benzyloxy)-2-(tert-butoxycarbonylamino)succinate

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Technology Process of (2S,3S)-1-((R)-1-(allyloxy)-14-methyl-1-oxopentadecan-3-yl)-4-cyclohexyl-3-(benzyloxy)-2-(tert-butoxycarbonylamino)succinate

There total 9 articles about (2S,3S)-1-((R)-1-(allyloxy)-14-methyl-1-oxopentadecan-3-yl)-4-cyclohexyl-3-(benzyloxy)-2-(tert-butoxycarbonylamino)succinate 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: 84.0%

: 936703-35-4
(R)-allyl 3-hydroxy-14-methylpentadecanoate

: 936703-51-4
(2R,3R)-2-(benzyloxy)-2-(tert-butoxycarbonylamino)-4-(cyclohexyloxy)-4-oxobutanoic acid

: 936703-49-0
(2S,3S)-1-((R)-1-(allyloxy)-14-methyl-1-oxopentadecan-3-yl)-4-cyclohexyl-3-(benzyloxy)-2-(tert-butoxycarbonylamino)succinate

Guidance literature:: With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at -15 - 20 ℃; for 15h;
DOI:10.1021/ja068455x

Reference yield:

: 106787-53-5
11-methyl-dodec-1-ene

: 936703-49-0
(2S,3S)-1-((R)-1-(allyloxy)-14-methyl-1-oxopentadecan-3-yl)-4-cyclohexyl-3-(benzyloxy)-2-(tert-butoxycarbonylamino)succinate

Guidance literature:: Multi-step reaction with 5 steps

1.1: 90 percent / Grubbs catalyst second generation / CH₂Cl₂ / 24 h / 50 °C

2.1: 98 percent / H₂ / Pd/C / ethanol / 24 h

3.1: TFA / CH₂Cl₂ / 20 °C

3.2: 90 percent / K₂CO₃ / methanol / 12 h

4.1: aq. Cs₂CO₃ / methanol / 0.25 h / 20 °C

4.2: 90 percent / dimethylformamide / 12 h

5.1: 84 percent / DMAP; EDCl / CH₂Cl₂ / 15 h / -15 - 20 °C

With dmap; hydrogen; caesium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; palladium on activated charcoal; In methanol; ethanol; dichloromethane;
DOI:10.1021/ja068455x

Reference yield:

: 936703-48-9
(S)-tert-butyl 3-acetoxy-14-methylpentadec-4-enoate

: 936703-49-0
(2S,3S)-1-((R)-1-(allyloxy)-14-methyl-1-oxopentadecan-3-yl)-4-cyclohexyl-3-(benzyloxy)-2-(tert-butoxycarbonylamino)succinate

Guidance literature:: Multi-step reaction with 4 steps

1.1: 98 percent / H₂ / Pd/C / ethanol / 24 h

2.1: TFA / CH₂Cl₂ / 20 °C

2.2: 90 percent / K₂CO₃ / methanol / 12 h

3.1: aq. Cs₂CO₃ / methanol / 0.25 h / 20 °C

3.2: 90 percent / dimethylformamide / 12 h

4.1: 84 percent / DMAP; EDCl / CH₂Cl₂ / 15 h / -15 - 20 °C

With dmap; hydrogen; caesium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; palladium on activated charcoal; In methanol; ethanol; dichloromethane;
DOI:10.1021/ja068455x