(2R,5R,3Z)-5-[(tert-butyldimethylsilyl)oxy]-4-chloro-5-phenyl-2-(prop-2-yn-1-yl)pent-3-enoyl-(R)-sultam

Base Information

Chemical Name:(2R,5R,3Z)-5-[(tert-butyldimethylsilyl)oxy]-4-chloro-5-phenyl-2-(prop-2-yn-1-yl)pent-3-enoyl-(R)-sultam
CAS No.:1394236-69-1
Molecular Formula:C₃₀H₄₂ClNO₄SSi
Molecular Weight:576.272
Hs Code.:

Synonyms:(2R,5R,3Z)-5-[(tert-butyldimethylsilyl)oxy]-4-chloro-5-phenyl-2-(prop-2-yn-1-yl)pent-3-enoyl-(R)-sultam

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Chemical Property of (2R,5R,3Z)-5-[(tert-butyldimethylsilyl)oxy]-4-chloro-5-phenyl-2-(prop-2-yn-1-yl)pent-3-enoyl-(R)-sultam

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Technology Process of (2R,5R,3Z)-5-[(tert-butyldimethylsilyl)oxy]-4-chloro-5-phenyl-2-(prop-2-yn-1-yl)pent-3-enoyl-(R)-sultam

There total 5 articles about (2R,5R,3Z)-5-[(tert-butyldimethylsilyl)oxy]-4-chloro-5-phenyl-2-(prop-2-yn-1-yl)pent-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: 82.0%

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

: 106-96-7
propargyl bromide

: 1394236-69-1
(2R,5R,3Z)-5-[(tert-butyldimethylsilyl)oxy]-4-chloro-5-phenyl-2-(prop-2-yn-1-yl)pent-3-enoyl-(R)-sultam

Guidance literature:: (5R,2E)-5-[(tert-butyldimethylsilyl)oxy]-4,4-dichloro-5-phenylpent-3-enoyl-(R)-sultam; With copper(l) iodide; methyllithium lithium bromide; In tetrahydrofuran; diethyl ether; at -78 - 0 ℃; for 0.666667h; Inert atmosphere;

With N,N,N,N,N,N-hexamethylphosphoric triamide; triphenyltin chloride; In tetrahydrofuran; diethyl ether; at -78 - -30 ℃; for 1h; Inert atmosphere;

propargyl bromide; In tetrahydrofuran; diethyl ether; at -30 - 20 ℃; for 20.5h; diastereoselective reaction; Inert atmosphere;
DOI:10.1021/ol301988d

Reference yield:

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

: 1394236-69-1
(2R,5R,3Z)-5-[(tert-butyldimethylsilyl)oxy]-4-chloro-5-phenyl-2-(prop-2-yn-1-yl)pent-3-enoyl-(R)-sultam

Guidance literature:: Multi-step reaction with 4 steps

1.1: 2,6-dimethylpyridine / dichloromethane / 12 h / 0 - 20 °C / Inert atmosphere

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

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

4.1: methyllithium lithium bromide; copper(l) iodide / tetrahydrofuran; diethyl ether / 0.67 h / -78 - 0 °C / Inert atmosphere

4.2: 1 h / -78 - -30 °C / Inert atmosphere

4.3: 20.5 h / -30 - 20 °C / Inert atmosphere

With 2,6-dimethylpyridine; copper(l) iodide; methyllithium lithium bromide; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; lithium chloride; In tetrahydrofuran; diethyl ether; dichloromethane; toluene; acetonitrile; 3.1: |Horner-Wadsworth-Emmons Olefination;
DOI:10.1021/ol301988d

Reference yield:

: 100-52-7
benzaldehyde

: 1394236-69-1
(2R,5R,3Z)-5-[(tert-butyldimethylsilyl)oxy]-4-chloro-5-phenyl-2-(prop-2-yn-1-yl)pent-3-enoyl-(R)-sultam

Guidance literature:: Multi-step reaction with 5 steps

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

2.1: 2,6-dimethylpyridine / dichloromethane / 12 h / 0 - 20 °C / Inert atmosphere

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

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

5.1: methyllithium lithium bromide; copper(l) iodide / tetrahydrofuran; diethyl ether / 0.67 h / -78 - 0 °C / Inert atmosphere

5.2: 1 h / -78 - -30 °C / Inert atmosphere

5.3: 20.5 h / -30 - 20 °C / Inert atmosphere

With 2,6-dimethylpyridine; copper(l) iodide; methyllithium lithium bromide; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; lithium chloride; (S)-4-Isopropyl-3-tosyl-[1,3,2]oxazaborolidin-5-one; In tetrahydrofuran; diethyl ether; dichloromethane; toluene; acetonitrile; 1.1: |Mukaiyama Aldol Addition / 4.1: |Horner-Wadsworth-Emmons Olefination;
DOI:10.1021/ol301988d