(E)-(R)-2-((2S,4S,5S)-3,4-Dimethyl-2-oxo-5-phenyl-2λ⁵-[1,3,2]oxazaphospholidin-2-yloxy)-2-((E)-3-phenyl-allyl)-pent-3-enenitrile

Base Information

• Chemical Name: (E)-(R)-2-((2S,4S,5S)-3,4-Dimethyl-2-oxo-5-phenyl-2λ⁵-[1,3,2]oxazaphospholidin-2-yloxy)-2-((E)-3-phenyl-allyl)-pent-3-enenitrile
• CAS No.: 195434-00-5
• Molecular Formula: C₂₄H₂₇N₂O₃P
• Molecular Weight: 422.464

Synonyms:(E)-(R)-2-((2S,4S,5S)-3,4-Dimethyl-2-oxo-5-phenyl-2λ⁵-[1,3,2]oxazaphospholidin-2-yloxy)-2-((E)-3-phenyl-allyl)-pent-3-enenitrile

Chemical Property of (E)-(R)-2-((2S,4S,5S)-3,4-Dimethyl-2-oxo-5-phenyl-2λ⁵-[1,3,2]oxazaphospholidin-2-yloxy)-2-((E)-3-phenyl-allyl)-pent-3-enenitrile

Chemical Property:

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Technology Process of (E)-(R)-2-((2S,4S,5S)-3,4-Dimethyl-2-oxo-5-phenyl-2λ⁵-[1,3,2]oxazaphospholidin-2-yloxy)-2-((E)-3-phenyl-allyl)-pent-3-enenitrile

There total 3 articles about (E)-(R)-2-((2S,4S,5S)-3,4-Dimethyl-2-oxo-5-phenyl-2λ⁵-[1,3,2]oxazaphospholidin-2-yloxy)-2-((E)-3-phenyl-allyl)-pent-3-enenitrile 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:

Cinnamyl bromide (4392-24-9) + (E)-2-((2S,4S,5S)-3,4-Dimethyl-2-oxo-5-phenyl-2λ5-[1,3,2]oxazaphospholidin-2-yloxy)-pent-3-enenitrile (195433-96-6) → (E)-(R)-2-((2S,4S,5S)-3,4-Dimethyl-2-oxo-5-phenyl-2λ5-[1,3,2]oxazaphospholidin-2-yloxy)-2-((E)-3-phenyl-allyl)-pent-3-enenitrile (195434-00-5)

Guidance literature:

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; n-butyllithium; In tetrahydrofuran; hexane; at -108 ℃; Yield given; 1.) 20 min, 2.) 4 h;

DOI:10.1021/jo970854a

Reference yield:

(E)-2-hydroxypent-3-enenitrile (193805-19-5) → (E)-(R)-2-((2S,4S,5S)-3,4-Dimethyl-2-oxo-5-phenyl-2λ5-[1,3,2]oxazaphospholidin-2-yloxy)-2-((E)-3-phenyl-allyl)-pent-3-enenitrile (195434-00-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 53 percent / Et₃N / CH₂Cl₂ / Ambient temperature

2: n-BuLi, DMPU / tetrahydrofuran; hexane / -108 °C / 1.) 20 min, 2.) 4 h

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; n-butyllithium; triethylamine; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1021/jo970854a

Reference yield:

(4S)-2-chloro-3,4r-dimethyl-5t-phenyl-[1,3,2]oxazaphospholidine 2ξ-oxide (13897-77-3,28080-18-4,28080-19-5,31060-10-3,31060-12-5,53625-09-5,53625-11-9,54750-12-8,54750-13-9,72691-41-9,149116-52-9) → (E)-(R)-2-((2S,4S,5S)-3,4-Dimethyl-2-oxo-5-phenyl-2λ5-[1,3,2]oxazaphospholidin-2-yloxy)-2-((E)-3-phenyl-allyl)-pent-3-enenitrile (195434-00-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 53 percent / Et₃N / CH₂Cl₂ / Ambient temperature

2: n-BuLi, DMPU / tetrahydrofuran; hexane / -108 °C / 1.) 20 min, 2.) 4 h

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; n-butyllithium; triethylamine; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1021/jo970854a

upstream raw materials:

Cinnamyl bromide

(E)-2-((2S,4S,5S)-3,4-Dimethyl-2-oxo-5-phenyl-2λ⁵-[1,3,2]oxazaphospholidin-2-yloxy)-pent-3-enenitrile

(E)-2-hydroxypent-3-enenitrile

(4S)-2-chloro-3,4r-dimethyl-5t-phenyl-[1,3,2]oxazaphospholidine 2ξ-oxide

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