(2S)-2-[(4R,5S)-8-(2,3-bis(tert-butoxycarbonyl)guanidino)-5-benzyloxycarbonylamino-4-hydroxy-octanoylamino]-4-methylpentanoic acid methyl ester

Base Information

Chemical Name:(2S)-2-[(4R,5S)-8-(2,3-bis(tert-butoxycarbonyl)guanidino)-5-benzyloxycarbonylamino-4-hydroxy-octanoylamino]-4-methylpentanoic acid methyl ester
CAS No.:866563-55-5
Molecular Formula:C₃₄H₅₅N₅O₁₀
Molecular Weight:693.838
Hs Code.:

(2S)-2-[(4R,5S)-8-(2,3-bis(tert-butoxycarbonyl)guanidino)-5-benzyloxycarbonylamino-4-hydroxy-octanoylamino]-4-methylpentanoic acid methyl ester

Synonyms:(2S)-2-[(4R,5S)-8-(2,3-bis(tert-butoxycarbonyl)guanidino)-5-benzyloxycarbonylamino-4-hydroxy-octanoylamino]-4-methylpentanoic acid methyl ester

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Chemical Property of (2S)-2-[(4R,5S)-8-(2,3-bis(tert-butoxycarbonyl)guanidino)-5-benzyloxycarbonylamino-4-hydroxy-octanoylamino]-4-methylpentanoic acid methyl ester

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Technology Process of (2S)-2-[(4R,5S)-8-(2,3-bis(tert-butoxycarbonyl)guanidino)-5-benzyloxycarbonylamino-4-hydroxy-octanoylamino]-4-methylpentanoic acid methyl ester

There total 6 articles about (2S)-2-[(4R,5S)-8-(2,3-bis(tert-butoxycarbonyl)guanidino)-5-benzyloxycarbonylamino-4-hydroxy-octanoylamino]-4-methylpentanoic 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: 74.0%

: di-tert-butyl((trifluoromethylsulfonamido)methylene)-dicarbamate

: 865622-24-8
(2S)-2-[(4R,5S)-5-benzyloxycarbonylamino-8-tert-butoxycarbonylamino-4-hydroxy-octanoylamino]-4-methylpentanoic acid methyl ester

: 866563-55-5
(2S)-2-[(4R,5S)-8-(2,3-bis(tert-butoxycarbonyl)guanidino)-5-benzyloxycarbonylamino-4-hydroxy-octanoylamino]-4-methylpentanoic acid methyl ester

Guidance literature:: (2S)-2-[(4R,5S)-5-benzyloxycarbonylamino-8-tert-butoxycarbonylamino-4-hydroxy-octanoylamino]-4-methylpentanoic acid methyl ester; With trifluoroacetic acid; In dichloromethane; for 0.5h;

di-tert-butyl((trifluoromethylsulfonamido)methylene)-dicarbamate; With triethylamine; In dichloromethane; for 2.25h;
DOI:10.1021/jo0505775

Reference yield:

: 18942-74-0
(2S)-2-acryloylamino-4-methylpentanoic acid methyl ester

: 866563-55-5
(2S)-2-[(4R,5S)-8-(2,3-bis(tert-butoxycarbonyl)guanidino)-5-benzyloxycarbonylamino-4-hydroxy-octanoylamino]-4-methylpentanoic acid methyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: 86 percent / samarium(II) diiodide / tetrahydrofuran / 120 h / -78 °C

2.1: 60 percent / lithium tri-tert-butoxyaluminum hydride / methanol / 16 h / -78 °C

3.1: trifluoroacetic acid / CH₂Cl₂ / 0.5 h

3.2: 74 percent / triethylamine / CH₂Cl₂ / 2.25 h

With samarium diiodide; lithium tri(t-butoxy)aluminum hydride; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/jo0505775

Reference yield:

: 7733-29-1,199924-46-4
Z-Orn(Boc)-OH

: 866563-55-5
(2S)-2-[(4R,5S)-8-(2,3-bis(tert-butoxycarbonyl)guanidino)-5-benzyloxycarbonylamino-4-hydroxy-octanoylamino]-4-methylpentanoic acid methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: 67 percent / EDC / CH₂Cl₂ / 0 - 20 °C

2.1: 86 percent / samarium(II) diiodide / tetrahydrofuran / 120 h / -78 °C

3.1: 60 percent / lithium tri-tert-butoxyaluminum hydride / methanol / 16 h / -78 °C

4.1: trifluoroacetic acid / CH₂Cl₂ / 0.5 h

4.2: 74 percent / triethylamine / CH₂Cl₂ / 2.25 h

With samarium diiodide; lithium tri(t-butoxy)aluminum hydride; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/jo0505775