(2R,3S)-6-((R)-1-Isopropyl-5-phenyl-pent-2-ynyl)-3,4-dimethyl-2-phenyl-[1,4]oxazepane-5,7-dione

Base Information

• Chemical Name: (2R,3S)-6-((R)-1-Isopropyl-5-phenyl-pent-2-ynyl)-3,4-dimethyl-2-phenyl-[1,4]oxazepane-5,7-dione
• CAS No.: 738628-05-2
• Molecular Formula: C₂₇H₃₁NO₃
• Molecular Weight: 417.548

Synonyms:(2R,3S)-6-((R)-1-Isopropyl-5-phenyl-pent-2-ynyl)-3,4-dimethyl-2-phenyl-[1,4]oxazepane-5,7-dione

Chemical Property of (2R,3S)-6-((R)-1-Isopropyl-5-phenyl-pent-2-ynyl)-3,4-dimethyl-2-phenyl-[1,4]oxazepane-5,7-dione

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Technology Process of (2R,3S)-6-((R)-1-Isopropyl-5-phenyl-pent-2-ynyl)-3,4-dimethyl-2-phenyl-[1,4]oxazepane-5,7-dione

There total 2 articles about (2R,3S)-6-((R)-1-Isopropyl-5-phenyl-pent-2-ynyl)-3,4-dimethyl-2-phenyl-[1,4]oxazepane-5,7-dione 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:

4-Phenyl-1-butyne (16520-62-0) + (2S,3S)-(Z)-isobutylidene-3,4-dimethyl-2-phenyl-[1,4]oxazepane-5,7-dione (123356-39-8) → (2R,3S)-6-((R)-1-Isopropyl-5-phenyl-pent-2-ynyl)-3,4-dimethyl-2-phenyl-[1,4]oxazepane-5,7-dione (738628-05-2)

Guidance literature:

With zinc trifluoromethanesulfonate; triethylamine; In dichloromethane; at 23 ℃; for 18h;

DOI:10.1021/ol0491585

Reference yield:

(2R,3S)-3,4-dimethyl-2-phenylperhydro-1,4-oxazepine-5,7-dione (67376-72-1) → (2R,3S)-6-((R)-1-Isopropyl-5-phenyl-pent-2-ynyl)-3,4-dimethyl-2-phenyl-[1,4]oxazepane-5,7-dione (738628-05-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 74 percent / pyridine; TiCl₄ / tetrahydrofuran / 16 h / -78 - 23 °C

2: Zn(OTf)2; Et₃N / CH₂Cl₂ / 18 h / 23 °C

With pyridine; titanium tetrachloride; zinc trifluoromethanesulfonate; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ol0491585

Reference yield:

(2R,3S)-6-((R)-1-Isopropyl-5-phenyl-pent-2-ynyl)-3,4-dimethyl-2-phenyl-[1,4]oxazepane-5,7-dione (738628-05-2) → 2-((R)-1-Isopropyl-5-phenyl-pent-2-ynyl)-malonic acid (1026528-21-1)

Guidance literature:

With potassium hydroxide; In propan-1-ol; for 16h; Heating;

DOI:10.1021/ol0491585

upstream raw materials:

4-Phenyl-1-butyne

(2S,3S)-(Z)-isobutylidene-3,4-dimethyl-2-phenyl-[1,4]oxazepane-5,7-dione

(2R,3S)-3,4-dimethyl-2-phenylperhydro-1,4-oxazepine-5,7-dione

Downstream raw materials:

2-((R)-1-Isopropyl-5-phenyl-pent-2-ynyl)-malonic acid

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