(R)-4-benzyl-3-((2R,3S,E)-2-chloro-3-hydroxy-6-methylhept-4-enoyl)-5,5-dimethyloxazolidin-2-one

Base Information

Chemical Name:(R)-4-benzyl-3-((2R,3S,E)-2-chloro-3-hydroxy-6-methylhept-4-enoyl)-5,5-dimethyloxazolidin-2-one
CAS No.:1312341-53-9
Molecular Formula:C₂₀H₂₆ClNO₄
Molecular Weight:379.884
Hs Code.:

Synonyms:(R)-4-benzyl-3-((2R,3S,E)-2-chloro-3-hydroxy-6-methylhept-4-enoyl)-5,5-dimethyloxazolidin-2-one

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Chemical Property of (R)-4-benzyl-3-((2R,3S,E)-2-chloro-3-hydroxy-6-methylhept-4-enoyl)-5,5-dimethyloxazolidin-2-one

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Technology Process of (R)-4-benzyl-3-((2R,3S,E)-2-chloro-3-hydroxy-6-methylhept-4-enoyl)-5,5-dimethyloxazolidin-2-one

There total 2 articles about (R)-4-benzyl-3-((2R,3S,E)-2-chloro-3-hydroxy-6-methylhept-4-enoyl)-5,5-dimethyloxazolidin-2-one 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: 75.0%

: 870196-41-1
(R)-4-benzyl-3-(2-chloroacetyl)-5,5-dimethyl-2-one

: 24502-08-7
(E)-4-methylpent-2-enal

: 1312341-53-9
(R)-4-benzyl-3-((2R,3S,E)-2-chloro-3-hydroxy-6-methylhept-4-enoyl)-5,5-dimethyloxazolidin-2-one

Guidance literature:: (R)-4-benzyl-3-(2-chloroacetyl)-5,5-dimethyl-2-one; With N-ethyl-N,N-diisopropylamine; 9-BBN triflate; In hexane; dichloromethane; at 0 ℃; for 1.5h; Inert atmosphere;

(E)-4-methylpent-2-enal; In hexane; dichloromethane; at -78 - 20 ℃; Inert atmosphere;
DOI:10.1021/ol2012023

Reference yield:

: 204851-73-0,352438-06-3
(R)-(+)-4-benzyl-5,5-dimethyl-2-oxazolidinone

: 1312341-53-9
(R)-4-benzyl-3-((2R,3S,E)-2-chloro-3-hydroxy-6-methylhept-4-enoyl)-5,5-dimethyloxazolidin-2-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere

1.2: 2 h / -78 °C / Inert atmosphere

2.1: N-ethyl-N,N-diisopropylamine; 9-BBN triflate / hexane; dichloromethane / 1.5 h / 0 °C / Inert atmosphere

2.2: -78 - 20 °C / Inert atmosphere

With n-butyllithium; N-ethyl-N,N-diisopropylamine; 9-BBN triflate; In tetrahydrofuran; hexane; dichloromethane; 2.1: asymmetric syn-aldol condensation / 2.2: asymmetric syn-aldol condensation;
DOI:10.1021/ol2012023

Reference yield: 76.0%

: 1312341-53-9
(R)-4-benzyl-3-((2R,3S,E)-2-chloro-3-hydroxy-6-methylhept-4-enoyl)-5,5-dimethyloxazolidin-2-one

: 1312341-54-0
(R)-4-benzyl-3-((2R,3S)-2-chloro-3-hydroxy-3-((1R,2S)-2-isopropylcyclopropyl)propanoyl)-5,5-dimethyloxazolidin-2-one

Guidance literature:: With diiodomethane; diethylzinc; In hexane; dichloromethane; at 0 ℃; for 2h; Inert atmosphere; Darkness;
DOI:10.1021/ol2012023