(S,2E,4E)-6-((S)-5-(((benzyloxy)carbonyl)amino)-2-((tertbutoxycarbonyl)amino)pentanamido)-7-phenylhepta-2,4-dienoic acid

Base Information

Chemical Name:(S,2E,4E)-6-((S)-5-(((benzyloxy)carbonyl)amino)-2-((tertbutoxycarbonyl)amino)pentanamido)-7-phenylhepta-2,4-dienoic acid
CAS No.:1424360-95-1
Molecular Formula:C₃₁H₃₉N₃O₇
Molecular Weight:565.667
Hs Code.:

Synonyms:(S,2E,4E)-6-((S)-5-(((benzyloxy)carbonyl)amino)-2-((tertbutoxycarbonyl)amino)pentanamido)-7-phenylhepta-2,4-dienoic acid

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Chemical Property of (S,2E,4E)-6-((S)-5-(((benzyloxy)carbonyl)amino)-2-((tertbutoxycarbonyl)amino)pentanamido)-7-phenylhepta-2,4-dienoic acid

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Technology Process of (S,2E,4E)-6-((S)-5-(((benzyloxy)carbonyl)amino)-2-((tertbutoxycarbonyl)amino)pentanamido)-7-phenylhepta-2,4-dienoic acid

There total 4 articles about (S,2E,4E)-6-((S)-5-(((benzyloxy)carbonyl)amino)-2-((tertbutoxycarbonyl)amino)pentanamido)-7-phenylhepta-2,4-dienoic 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: 96.5%

: 1424360-84-8
(2E,4E)-ethyl 6-(5-(((benzyloxy)carbonyl)amino)-2-((tert-butoxycarbonyl)amino)pentanamido)-7-phenylhepta-2,4-dienoate

: 1424360-95-1
(S,2E,4E)-6-((S)-5-(((benzyloxy)carbonyl)amino)-2-((tertbutoxycarbonyl)amino)pentanamido)-7-phenylhepta-2,4-dienoic acid

Guidance literature:: With lithium hydroxide; In tetrahydrofuran; at 20 ℃; for 36h;

Reference yield:

: 1424360-83-7
(2E,4E)-ethyl 6-((tert-butoxycarbonyl)amino)-7-phenylhepta-2,4-dienoate

: 1424360-95-1
(S,2E,4E)-6-((S)-5-(((benzyloxy)carbonyl)amino)-2-((tertbutoxycarbonyl)amino)pentanamido)-7-phenylhepta-2,4-dienoic acid

Guidance literature:: Multi-step reaction with 3 steps

1: trifluoroacetic acid / dichloromethane / 36 h / 20 °C

2: triethylamine; dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 4 h / 20 °C

3: lithium hydroxide; water / methanol; tetrahydrofuran / 36 h / 20 °C

With dmap; water; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; lithium hydroxide; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1016/j.bmcl.2012.12.100

Reference yield:

: 72155-45-4
Boc-L-phenylalaninal

: 1424360-95-1
(S,2E,4E)-6-((S)-5-(((benzyloxy)carbonyl)amino)-2-((tertbutoxycarbonyl)amino)pentanamido)-7-phenylhepta-2,4-dienoic acid

Guidance literature:: Multi-step reaction with 4 steps

1.1: potassium tert-butylate / tetrahydrofuran / 1 h / 0 °C

1.2: 3 h / 20 °C

2.1: trifluoroacetic acid / dichloromethane / 36 h / 20 °C

3.1: triethylamine; dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 4 h / 20 °C

4.1: lithium hydroxide; water / methanol; tetrahydrofuran / 36 h / 20 °C

With dmap; potassium tert-butylate; water; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; lithium hydroxide; In tetrahydrofuran; methanol; dichloromethane; 1.1: |Horner-Wadsworth-Emmons Olefination / 1.2: |Horner-Wadsworth-Emmons Olefination;
DOI:10.1016/j.bmcl.2012.12.100