(5R,2E)-5-[(tert-butyldimethylsilyl)oxy]-4,4-dichloro-5-phenylpent-3-enoyl-(R)-sultam

Base Information

Chemical Name:(5R,2E)-5-[(tert-butyldimethylsilyl)oxy]-4,4-dichloro-5-phenylpent-3-enoyl-(R)-sultam
CAS No.:1394236-62-4
Molecular Formula:C₂₇H₃₉Cl₂NO₄SSi
Molecular Weight:572.668
Hs Code.:

Synonyms:(5R,2E)-5-[(tert-butyldimethylsilyl)oxy]-4,4-dichloro-5-phenylpent-3-enoyl-(R)-sultam

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Chemical Property of (5R,2E)-5-[(tert-butyldimethylsilyl)oxy]-4,4-dichloro-5-phenylpent-3-enoyl-(R)-sultam

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Technology Process of (5R,2E)-5-[(tert-butyldimethylsilyl)oxy]-4,4-dichloro-5-phenylpent-3-enoyl-(R)-sultam

There total 4 articles about (5R,2E)-5-[(tert-butyldimethylsilyl)oxy]-4,4-dichloro-5-phenylpent-3-enoyl-(R)-sultam 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:

: C₁₅H₂₂Cl₂O₂Si

: 120297-92-9
diethyl 2-oxo-2-((1S,2R)-N-camphor-10,2-sultam)-ethylphosphonate

: 1394236-62-4
(5R,2E)-5-[(tert-butyldimethylsilyl)oxy]-4,4-dichloro-5-phenylpent-3-enoyl-(R)-sultam

Guidance literature:: With N-ethyl-N,N-diisopropylamine; lithium chloride; In acetonitrile; at 0 - 20 ℃; for 12.5h; Inert atmosphere;
DOI:10.1021/ol301988d

Reference yield:

: (3R)-methyl 2,2-dichloro-3-hydroxy-3-phenylpropionate

: 1394236-62-4
(5R,2E)-5-[(tert-butyldimethylsilyl)oxy]-4,4-dichloro-5-phenylpent-3-enoyl-(R)-sultam

Guidance literature:: Multi-step reaction with 3 steps

1: 2,6-dimethylpyridine / dichloromethane / 12 h / 0 - 20 °C / Inert atmosphere

2: diisobutylaluminium hydride / dichloromethane; toluene / 2 h / -78 °C / Inert atmosphere

3: lithium chloride; N-ethyl-N,N-diisopropylamine / acetonitrile / 12.5 h / 0 - 20 °C / Inert atmosphere

With 2,6-dimethylpyridine; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; lithium chloride; In dichloromethane; toluene; acetonitrile; 3: |Horner-Wadsworth-Emmons Olefination;
DOI:10.1021/ol301988d

Reference yield:

: 100-52-7
benzaldehyde

: 1394236-62-4
(5R,2E)-5-[(tert-butyldimethylsilyl)oxy]-4,4-dichloro-5-phenylpent-3-enoyl-(R)-sultam

Guidance literature:: Multi-step reaction with 4 steps

1: (S)-4-Isopropyl-3-tosyl-[1,3,2]oxazaborolidin-5-one / dichloromethane / -78 °C / Inert atmosphere

2: 2,6-dimethylpyridine / dichloromethane / 12 h / 0 - 20 °C / Inert atmosphere

3: diisobutylaluminium hydride / dichloromethane; toluene / 2 h / -78 °C / Inert atmosphere

4: lithium chloride; N-ethyl-N,N-diisopropylamine / acetonitrile / 12.5 h / 0 - 20 °C / Inert atmosphere

With 2,6-dimethylpyridine; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; lithium chloride; (S)-4-Isopropyl-3-tosyl-[1,3,2]oxazaborolidin-5-one; In dichloromethane; toluene; acetonitrile; 1: |Mukaiyama Aldol Addition / 4: |Horner-Wadsworth-Emmons Olefination;
DOI:10.1021/ol301988d