N-[(1S-(1α,2α,1'α))-2-[2'-(N-(tert-butoxycarbonyl)-L-tyrosine)amino]ethan-1'-ol-cyclopropan-1-oyl]-L-phenylalanine-L-leucine methyl ester

Base Information

Chemical Name:N-[(1S-(1α,2α,1'α))-2-[2'-(N-(tert-butoxycarbonyl)-L-tyrosine)amino]ethan-1'-ol-cyclopropan-1-oyl]-L-phenylalanine-L-leucine methyl ester
CAS No.:264921-43-9
Molecular Formula:C₃₆H₅₀N₄O₉
Molecular Weight:682.814
Hs Code.:

Synonyms:N-[(1S-(1α,2α,1'α))-2-[2'-(N-(tert-butoxycarbonyl)-L-tyrosine)amino]ethan-1'-ol-cyclopropan-1-oyl]-L-phenylalanine-L-leucine methyl ester

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Chemical Property of N-[(1S-(1α,2α,1'α))-2-[2'-(N-(tert-butoxycarbonyl)-L-tyrosine)amino]ethan-1'-ol-cyclopropan-1-oyl]-L-phenylalanine-L-leucine methyl ester

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Technology Process of N-[(1S-(1α,2α,1'α))-2-[2'-(N-(tert-butoxycarbonyl)-L-tyrosine)amino]ethan-1'-ol-cyclopropan-1-oyl]-L-phenylalanine-L-leucine methyl ester

There total 9 articles about N-[(1S-(1α,2α,1'α))-2-[2'-(N-(tert-butoxycarbonyl)-L-tyrosine)amino]ethan-1'-ol-cyclopropan-1-oyl]-L-phenylalanine-L-leucine 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: 73.0%

: 3978-80-1
Boc-Tyr-OH

: 264921-42-8
N-[(1S-(1α,2α,1'α))-2-(2'-amino)ethan-1'-ol-cyclopropan-1-oyl]-L-phenylalanine-L-leucine methyl ester

: 264921-43-9
N-[(1S-(1α,2α,1'α))-2-[2'-(N-(tert-butoxycarbonyl)-L-tyrosine)amino]ethan-1'-ol-cyclopropan-1-oyl]-L-phenylalanine-L-leucine methyl ester

Guidance literature:: With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 14h;
DOI:10.1021/jo991288h

Reference yield:

: 3303-55-7
L-Phe-Leu

: 264921-43-9
N-[(1S-(1α,2α,1'α))-2-[2'-(N-(tert-butoxycarbonyl)-L-tyrosine)amino]ethan-1'-ol-cyclopropan-1-oyl]-L-phenylalanine-L-leucine methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 60 percent / Me₃Al / hexane; 1,2-dichloro-ethane / 24 h / Heating

2: 95 percent / diethyl ether

3: 90 percent / H₂ / Pd/C / methanol / 760.05 Torr

4: 73 percent / EDCI; HOBt / dimethylformamide / 14 h / 0 - 20 °C

With hydrogen; trimethylaluminum; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; palladium on activated charcoal; In methanol; diethyl ether; hexane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; 1: Ring cleavage / 2: Esterification / 3: Reduction / 4: Condensation;
DOI:10.1021/jo991288h

Reference yield:

: 156418-79-0
1,4-pentadienyl-3-diazoacetate

: 264921-43-9
N-[(1S-(1α,2α,1'α))-2-[2'-(N-(tert-butoxycarbonyl)-L-tyrosine)amino]ethan-1'-ol-cyclopropan-1-oyl]-L-phenylalanine-L-leucine methyl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: Rh₂[(5S)-MEPY]4 / CH₂Cl₂ / Heating

2.1: O₃ / methanol; CH₂Cl₂ / -78 °C

2.2: 60 percent / NaBH₄ / methanol; CH₂Cl₂ / 0.5 h / -78 - 0 °C

3.1: 90 percent / Et₃N / CH₂Cl₂ / 1 h / 0 °C

4.1: 0.15 g / NaN₃ / dimethylformamide / 12 h / 65 °C

5.1: 60 percent / Me₃Al / hexane; 1,2-dichloro-ethane / 24 h / Heating

6.1: 95 percent / diethyl ether

7.1: 90 percent / H₂ / Pd/C / methanol / 760.05 Torr

8.1: 73 percent / EDCI; HOBt / dimethylformamide / 14 h / 0 - 20 °C

With sodium azide; Rh₂[(2S)-5-hydroxypyrrolidine-2-COOMe]4; hydrogen; trimethylaluminum; benzotriazol-1-ol; ozone; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; palladium on activated charcoal; In methanol; diethyl ether; hexane; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; 1.1: Cyclization / 2.1: ozonolysis / 2.2: Reduction / 3.1: Condensation / 4.1: Substitution / 5.1: Ring cleavage / 6.1: Esterification / 7.1: Reduction / 8.1: Condensation;
DOI:10.1021/jo991288h