N₁,N₆-bis[(1S)-2-methyl-1-(methylcarbamoyl)propyl]-(2R,3R,4R,5R)-2-{4-[(E)-2-(N-{2-[2-(2-aminoethoxy)ethoxy]ethyl})carbamoylethenyl]benzyloxy}-5-(4-bromobenzyloxy)-3,4-dihydroxyhexanediamide

Base Information

• Chemical Name: N₁,N₆-bis[(1S)-2-methyl-1-(methylcarbamoyl)propyl]-(2R,3R,4R,5R)-2-{4-[(E)-2-(N-{2-[2-(2-aminoethoxy)ethoxy]ethyl})carbamoylethenyl]benzyloxy}-5-(4-bromobenzyloxy)-3,4-dihydroxyhexanediamide
• CAS No.: 361433-05-8
• Molecular Formula: C₄₁H₆₁BrN₆O₁₁
• Molecular Weight: 893.873

Synonyms:N₁,N₆-bis[(1S)-2-methyl-1-(methylcarbamoyl)propyl]-(2R,3R,4R,5R)-2-{4-[(E)-2-(N-{2-[2-(2-aminoethoxy)ethoxy]ethyl})carbamoylethenyl]benzyloxy}-5-(4-bromobenzyloxy)-3,4-dihydroxyhexanediamide

Chemical Property of N₁,N₆-bis[(1S)-2-methyl-1-(methylcarbamoyl)propyl]-(2R,3R,4R,5R)-2-{4-[(E)-2-(N-{2-[2-(2-aminoethoxy)ethoxy]ethyl})carbamoylethenyl]benzyloxy}-5-(4-bromobenzyloxy)-3,4-dihydroxyhexanediamide

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Technology Process of N₁,N₆-bis[(1S)-2-methyl-1-(methylcarbamoyl)propyl]-(2R,3R,4R,5R)-2-{4-[(E)-2-(N-{2-[2-(2-aminoethoxy)ethoxy]ethyl})carbamoylethenyl]benzyloxy}-5-(4-bromobenzyloxy)-3,4-dihydroxyhexanediamide

There total 3 articles about N₁,N₆-bis[(1S)-2-methyl-1-(methylcarbamoyl)propyl]-(2R,3R,4R,5R)-2-{4-[(E)-2-(N-{2-[2-(2-aminoethoxy)ethoxy]ethyl})carbamoylethenyl]benzyloxy}-5-(4-bromobenzyloxy)-3,4-dihydroxyhexanediamide 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: 98.0%

N1,N6-bis[(1S)-2-methyl-1-(methylcarbamoyl)propyl]-(2R,3R,4R,5R)-2-{4-[(E)-2-(N-{2-[2-(2-t-butoxycarbonylaminoethoxy)ethoxy]ethyl})carbamoylethenyl]benzyloxy}-5-(4-bromobenzyloxy)-3,4-dihydroxyhexanediamide (361433-04-7) → N1,N6-bis[(1S)-2-methyl-1-(methylcarbamoyl)propyl]-(2R,3R,4R,5R)-2-{4-[(E)-2-(N-{2-[2-(2-aminoethoxy)ethoxy]ethyl})carbamoylethenyl]benzyloxy}-5-(4-bromobenzyloxy)-3,4-dihydroxyhexanediamide (361433-05-8)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; for 0.166667h;

DOI:10.1016/S0928-0987(01)00109-9

Reference yield:

tert-butyl {2-[2-(2-aminoethoxy)ethoxy]ethyl}carbamate (153086-78-3) → N1,N6-bis[(1S)-2-methyl-1-(methylcarbamoyl)propyl]-(2R,3R,4R,5R)-2-{4-[(E)-2-(N-{2-[2-(2-aminoethoxy)ethoxy]ethyl})carbamoylethenyl]benzyloxy}-5-(4-bromobenzyloxy)-3,4-dihydroxyhexanediamide (361433-05-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 92 percent / diisopropylethylamine / CH₂Cl₂ / 1 h / 20 °C

2: 15 percent / diisopropylethylamine; P(o-Tol)3 / Pd(OAc)2 / H₂O; dimethylformamide / 8 h / 80 °C / in sealed tube

3: 98 percent / TFA / CH₂Cl₂ / 0.17 h

With N-ethyl-N,N-diisopropylamine; tris-(o-tolyl)phosphine; trifluoroacetic acid; palladium diacetate; In dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/S0928-0987(01)00109-9

Reference yield:

N-{2-[2-(2-tert-butoxycarbonylaminoethoxy)ethoxy]ethyl}acrylamide (361433-00-3) → N1,N6-bis[(1S)-2-methyl-1-(methylcarbamoyl)propyl]-(2R,3R,4R,5R)-2-{4-[(E)-2-(N-{2-[2-(2-aminoethoxy)ethoxy]ethyl})carbamoylethenyl]benzyloxy}-5-(4-bromobenzyloxy)-3,4-dihydroxyhexanediamide (361433-05-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 15 percent / diisopropylethylamine; P(o-Tol)3 / Pd(OAc)2 / H₂O; dimethylformamide / 8 h / 80 °C / in sealed tube

2: 98 percent / TFA / CH₂Cl₂ / 0.17 h

With N-ethyl-N,N-diisopropylamine; tris-(o-tolyl)phosphine; trifluoroacetic acid; palladium diacetate; In dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/S0928-0987(01)00109-9

upstream raw materials:

N₁,N₆-bis[(1S)-2-methyl-1-(methylcarbamoyl)propyl]-(2R,3R,4R,5R)-2-{4-[(E)-2-(N-{2-[2-(2-t-butoxycarbonylaminoethoxy)ethoxy]ethyl})carbamoylethenyl]benzyloxy}-5-(4-bromobenzyloxy)-3,4-dihydroxyhexanediamide

tert-butyl {2-[2-(2-aminoethoxy)ethoxy]ethyl}carbamate

N-{2-[2-(2-tert-butoxycarbonylaminoethoxy)ethoxy]ethyl}acrylamide

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