(2S,3S)-3-((S)-1,2-bis(benzyloxy)ethyl)-2-fluoro-N-methoxy-N-methylpent-4-enamide

Base Information

Chemical Name:(2S,3S)-3-((S)-1,2-bis(benzyloxy)ethyl)-2-fluoro-N-methoxy-N-methylpent-4-enamide
CAS No.:1309594-25-9
Molecular Formula:C₂₃H₂₈FNO₄
Molecular Weight:401.478
Hs Code.:

Synonyms:(2S,3S)-3-((S)-1,2-bis(benzyloxy)ethyl)-2-fluoro-N-methoxy-N-methylpent-4-enamide

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Chemical Property of (2S,3S)-3-((S)-1,2-bis(benzyloxy)ethyl)-2-fluoro-N-methoxy-N-methylpent-4-enamide

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Technology Process of (2S,3S)-3-((S)-1,2-bis(benzyloxy)ethyl)-2-fluoro-N-methoxy-N-methylpent-4-enamide

There total 3 articles about (2S,3S)-3-((S)-1,2-bis(benzyloxy)ethyl)-2-fluoro-N-methoxy-N-methylpent-4-enamide 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: 87.0%

: 1309594-24-8
(2S,3S)-methyl 3-((S)-1,2-bis(benzyloxy)ethyl)-2-fluoropent-4-enoate

: 6638-79-5
N,O-dimethylhydroxylamine*hydrochloride

: 1309594-25-9
(2S,3S)-3-((S)-1,2-bis(benzyloxy)ethyl)-2-fluoro-N-methoxy-N-methylpent-4-enamide

Guidance literature:: N,O-dimethylhydroxylamine*hydrochloride; With trimethylaluminum; In dichloromethane; toluene; at 0 ℃; for 1h;

(2S,3S)-methyl 3-((S)-1,2-bis(benzyloxy)ethyl)-2-fluoropent-4-enoate; In dichloromethane; toluene; at 0 - 20 ℃; for 24h;
DOI:10.1016/j.tet.2011.03.054

Reference yield:

: 1309594-23-7
(S,E)-4,5-bis(benzyloxy)pent-2-enyl 2-bromo-2-fluoroacetate

: 1309594-25-9
(2S,3S)-3-((S)-1,2-bis(benzyloxy)ethyl)-2-fluoro-N-methoxy-N-methylpent-4-enamide

Guidance literature:: Multi-step reaction with 2 steps

1.1: chloro-trimethyl-silane; zinc / acetonitrile / 10.33 h / 100 °C

1.2: 3 h / 20 °C

2.1: trimethylaluminum / dichloromethane; toluene / 1 h / 0 °C

2.2: 24 h / 0 - 20 °C

With chloro-trimethyl-silane; trimethylaluminum; zinc; In dichloromethane; toluene; acetonitrile; 1.1: Reformatsky-Claisen rearrangement;
DOI:10.1016/j.tet.2011.03.054

Reference yield:

: 1001273-06-8
(S,E)-4,5-bis(benzyloxy)pent-2-en-1-ol

: 1309594-25-9
(2S,3S)-3-((S)-1,2-bis(benzyloxy)ethyl)-2-fluoro-N-methoxy-N-methylpent-4-enamide

Guidance literature:: Multi-step reaction with 3 steps

1.1: pyridine / dichloromethane / 13 h / 0 - 20 °C

2.1: chloro-trimethyl-silane; zinc / acetonitrile / 10.33 h / 100 °C

2.2: 3 h / 20 °C

3.1: trimethylaluminum / dichloromethane; toluene / 1 h / 0 °C

3.2: 24 h / 0 - 20 °C

With pyridine; chloro-trimethyl-silane; trimethylaluminum; zinc; In dichloromethane; toluene; acetonitrile; 2.1: Reformatsky-Claisen rearrangement;
DOI:10.1016/j.tet.2011.03.054