(2S,9R,12S)-2,6-cyclo-12,16-cyclo-6,10,16-triaza-9-benzyl-19-(benzyloxycarbonylamino)-11-oxononadecanoic acid methyl ester

Base Information

Chemical Name:(2S,9R,12S)-2,6-cyclo-12,16-cyclo-6,10,16-triaza-9-benzyl-19-(benzyloxycarbonylamino)-11-oxononadecanoic acid methyl ester
CAS No.:866395-30-4
Molecular Formula:C₃₂H₄₄N₄O₅
Molecular Weight:564.725
Hs Code.:

Synonyms:(2S,9R,12S)-2,6-cyclo-12,16-cyclo-6,10,16-triaza-9-benzyl-19-(benzyloxycarbonylamino)-11-oxononadecanoic acid methyl ester

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Chemical Property of (2S,9R,12S)-2,6-cyclo-12,16-cyclo-6,10,16-triaza-9-benzyl-19-(benzyloxycarbonylamino)-11-oxononadecanoic acid methyl ester

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Technology Process of (2S,9R,12S)-2,6-cyclo-12,16-cyclo-6,10,16-triaza-9-benzyl-19-(benzyloxycarbonylamino)-11-oxononadecanoic acid methyl ester

There total 11 articles about (2S,9R,12S)-2,6-cyclo-12,16-cyclo-6,10,16-triaza-9-benzyl-19-(benzyloxycarbonylamino)-11-oxononadecanoic acid methyl 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: 76.0%

: (S)-1-((R)-3-Amino-4-phenyl-butyl)-pyrrolidine-2-carboxylic acid methyl ester; hydrochloride

: 295343-27-0
(2S)-N-(N'-(benzyloxycarbonyl)-3'-aminopropyl)-proline

: 866395-30-4
(2S,9R,12S)-2,6-cyclo-12,16-cyclo-6,10,16-triaza-9-benzyl-19-(benzyloxycarbonylamino)-11-oxononadecanoic acid methyl ester

Guidance literature:: With triethylamine; isobutyl chloroformate; In dichloromethane; at -20 - 20 ℃;
DOI:10.1016/j.tet.2005.07.049

Reference yield:

: 348184-48-5
(S)-N-(benzyloxycarbonyl)-3-amino-4-phenylbutan-1-ol

: 866395-30-4
(2S,9R,12S)-2,6-cyclo-12,16-cyclo-6,10,16-triaza-9-benzyl-19-(benzyloxycarbonylamino)-11-oxononadecanoic acid methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 99 percent / Et₃N / CH₂Cl₂ / cooling

2: 64 percent / Et₃N / acetonitrile / 20 - 50 °C

3: 99 percent / H₂; HCl / Pd-C / methanol

4: 76 percent / Et₃N; i-BuOCOCl / CH₂Cl₂ / -20 - 20 °C

With hydrogenchloride; hydrogen; triethylamine; isobutyl chloroformate; palladium on activated charcoal; In methanol; dichloromethane; acetonitrile;
DOI:10.1016/j.tet.2005.07.049

Reference yield:

: 866395-47-3
(R)-1-diazo-3-phthalimido-4-phenylbutan-2-one

: 866395-30-4
(2S,9R,12S)-2,6-cyclo-12,16-cyclo-6,10,16-triaza-9-benzyl-19-(benzyloxycarbonylamino)-11-oxononadecanoic acid methyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 77 percent / PhCO₂Ag; Et₃N / 2 h / Heating

2: LiBH₄ / tetrahydrofuran; H₂O / 1 h

3: AcOH / 80 °C

4: aq. NaOH / CH₂Cl₂ / 20 °C

5: 99 percent / Et₃N / CH₂Cl₂ / cooling

6: 64 percent / Et₃N / acetonitrile / 20 - 50 °C

7: 99 percent / H₂; HCl / Pd-C / methanol

8: 76 percent / Et₃N; i-BuOCOCl / CH₂Cl₂ / -20 - 20 °C

With hydrogenchloride; sodium hydroxide; lithium borohydride; hydrogen; silver benzoate; acetic acid; triethylamine; isobutyl chloroformate; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; acetonitrile; 1: Wolff rearrangement;
DOI:10.1016/j.tet.2005.07.049