tert-butyl 2-((3R,11S,E)-3-benzyl-5,12-dioxo-1-oxa-4-azacyclododec-8-en-11-yl)acetate

Base Information

• Chemical Name: tert-butyl 2-((3R,11S,E)-3-benzyl-5,12-dioxo-1-oxa-4-azacyclododec-8-en-11-yl)acetate
• CAS No.: 1395847-90-1
• Molecular Formula: C₂₃H₃₁NO₅
• Molecular Weight: 401.503
• Mol file: 1395847-90-1.mol

Synonyms:tert-butyl 2-((3R,11S,E)-3-benzyl-5,12-dioxo-1-oxa-4-azacyclododec-8-en-11-yl)acetate

Chemical Property of tert-butyl 2-((3R,11S,E)-3-benzyl-5,12-dioxo-1-oxa-4-azacyclododec-8-en-11-yl)acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl 2-((3R,11S,E)-3-benzyl-5,12-dioxo-1-oxa-4-azacyclododec-8-en-11-yl)acetate

There total 2 articles about tert-butyl 2-((3R,11S,E)-3-benzyl-5,12-dioxo-1-oxa-4-azacyclododec-8-en-11-yl)acetate 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: 65.0%

(S)-4-tert-butyl 1-((R)-2-(pent-4-enamido)-3-phenylpropyl)-2-allylsuccinate (1395847-83-2) → tert-butyl 2-((3R,11S,E)-3-benzyl-5,12-dioxo-1-oxa-4-azacyclododec-8-en-11-yl)acetate (1395847-90-1)

Guidance literature:

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In toluene; at 20 ℃; Inert atmosphere;

DOI:10.1021/ml300172p

Reference yield:

(R)-N-(1-hydroxy-3-phenylpropan-2-yl)pent-4-enamide (1395847-88-7) → tert-butyl 2-((3R,11S,E)-3-benzyl-5,12-dioxo-1-oxa-4-azacyclododec-8-en-11-yl)acetate (1395847-90-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 20 °C / Inert atmosphere

2: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / toluene / 20 °C / Inert atmosphere

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; toluene;

DOI:10.1021/ml300172p

Reference yield:

tert-butyl 2-((3R,11S,E)-3-benzyl-5,12-dioxo-1-oxa-4-azacyclododec-8-en-11-yl)acetate (1395847-90-1) → 2-((3R,11S,E)-3-benzyl-5,12-dioxo-1-oxa-4-azacyclododec-8-en-11-yl)acetic acid

Guidance literature:

With trifluoroacetic acid; In dichloromethane; for 4h; Cooling with ice;

DOI:10.1021/ml300172p

upstream raw materials:

(S)-4-tert-butyl 1-((R)-2-(pent-4-enamido)-3-phenylpropyl)-2-allylsuccinate

(R)-N-(1-hydroxy-3-phenylpropan-2-yl)pent-4-enamide

Downstream raw materials:

2-((3R,11S,E)-3-benzyl-5,12-dioxo-1-oxa-4-azacyclododec-8-en-11-yl)-N-(4-chlorobenzyl)acetamide