ethyl (2R,3S,4R)-5-benzyloxy-3,4-(dimethylmethylenedioxy)-2-hydroxy-3-(methylthio)carbonyl-2-(3-phenylpropyl)pentanoate

Base Information

Chemical Name:ethyl (2R,3S,4R)-5-benzyloxy-3,4-(dimethylmethylenedioxy)-2-hydroxy-3-(methylthio)carbonyl-2-(3-phenylpropyl)pentanoate
CAS No.:871514-37-3
Molecular Formula:C₂₈H₃₆O₇S
Molecular Weight:516.656
Hs Code.:

Synonyms:ethyl (2R,3S,4R)-5-benzyloxy-3,4-(dimethylmethylenedioxy)-2-hydroxy-3-(methylthio)carbonyl-2-(3-phenylpropyl)pentanoate

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Chemical Property of ethyl (2R,3S,4R)-5-benzyloxy-3,4-(dimethylmethylenedioxy)-2-hydroxy-3-(methylthio)carbonyl-2-(3-phenylpropyl)pentanoate

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Technology Process of ethyl (2R,3S,4R)-5-benzyloxy-3,4-(dimethylmethylenedioxy)-2-hydroxy-3-(methylthio)carbonyl-2-(3-phenylpropyl)pentanoate

There total 6 articles about ethyl (2R,3S,4R)-5-benzyloxy-3,4-(dimethylmethylenedioxy)-2-hydroxy-3-(methylthio)carbonyl-2-(3-phenylpropyl)pentanoate 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: 72.0%

: 81867-09-6
ethyl 2-oxo-5-phenylpentanoate

: 191934-88-0
(R,Z)-4-(benzyloxy)methyl-5-[methylthio(trimethylsilyloxy)methylene]-2,2-dimethyl-1,3-dioxolane

: 871514-37-3
ethyl (2R,3S,4R)-5-benzyloxy-3,4-(dimethylmethylenedioxy)-2-hydroxy-3-(methylthio)carbonyl-2-(3-phenylpropyl)pentanoate

: 871514-38-4
ethyl (2S,3S,4R)-5-benzyloxy-3,4-(dimethylmethylenedioxy)-2-hydroxy-3-(methylthio)carbonyl-2-(3-phenylpropyl)pentanoate

Guidance literature:: With tin(II) trifluoromethanesulfonate; In various solvent(s); at -78 ℃; for 0.5h;
DOI:10.1016/j.tet.2005.09.030

Reference yield:

: (4S,5R)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolane-4-carbonyl chloride

: 871514-37-3
ethyl (2R,3S,4R)-5-benzyloxy-3,4-(dimethylmethylenedioxy)-2-hydroxy-3-(methylthio)carbonyl-2-(3-phenylpropyl)pentanoate

Guidance literature:: Multi-step reaction with 3 steps

1.1: 77 percent / n-Bu₄NI / CH₂Cl₂; H₂O / 0.17 h / 0 °C

2.1: butyllithium; 1,1,1,3,3,3-hexamethyldisilazane / hexane; tetrahydrofuran / 0.5 h / -78 °C

2.2: 95 percent / tetrahydrofuran; hexane / -78 - 20 °C

3.1: 28 percent / Sn(OTf)2 / various solvent(s) / 0.5 h / -78 °C

With tin(II) trifluoromethanesulfonate; n-butyllithium; tetra-(n-butyl)ammonium iodide; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; hexane; dichloromethane; water; 3.1: aldol coupling;
DOI:10.1016/j.tet.2005.09.030

Reference yield:

: 871514-57-7
ethyl [2S,2(1R,2S),3S,4R]-5-benzyloxy-2-[1,2-(diethylmethylenedioxy)-3-[(2-methoxyethoxy)methoxy]propyl]-3,4-(dimethylmethylenedioxy)-2-hydroxy-3-(methylthio)carbonylpentanoate

: 871514-37-3
ethyl (2R,3S,4R)-5-benzyloxy-3,4-(dimethylmethylenedioxy)-2-hydroxy-3-(methylthio)carbonyl-2-(3-phenylpropyl)pentanoate

Guidance literature:: Multi-step reaction with 3 steps

1.1: 20 percent / KHMDS / toluene; tetrahydrofuran / -78 - -23 °C

2.1: butyllithium; 1,1,1,3,3,3-hexamethyldisilazane / hexane; tetrahydrofuran / 0.5 h / -78 °C

2.2: 95 percent / tetrahydrofuran; hexane / -78 - 20 °C

3.1: 28 percent / Sn(OTf)2 / various solvent(s) / 0.5 h / -78 °C

With tin(II) trifluoromethanesulfonate; n-butyllithium; potassium hexamethylsilazane; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; hexane; toluene; 1.1: aldol coupling / 3.1: aldol coupling;
DOI:10.1016/j.tet.2005.09.030