ethyl [2R,2(1R,2S),3S,4R]-5-benzyloxy-2-[3-benzyloxy-1,2-(diethylmethylenedioxy)propyl]-3,4-(dimethylmethylenedioxy)-2-hydroxy-3-(methylthio)carbonylpentanoate

Base Information

Chemical Name:ethyl [2R,2(1R,2S),3S,4R]-5-benzyloxy-2-[3-benzyloxy-1,2-(diethylmethylenedioxy)propyl]-3,4-(dimethylmethylenedioxy)-2-hydroxy-3-(methylthio)carbonylpentanoate
CAS No.:871514-48-6
Molecular Formula:C₃₄H₄₆O₁₀S
Molecular Weight:646.799
Hs Code.:

ethyl [2R,2(1R,2S),3S,4R]-5-benzyloxy-2-[3-benzyloxy-1,2-(diethylmethylenedioxy)propyl]-3,4-(dimethylmethylenedioxy)-2-hydroxy-3-(methylthio)carbonylpentanoate

Synonyms:ethyl [2R,2(1R,2S),3S,4R]-5-benzyloxy-2-[3-benzyloxy-1,2-(diethylmethylenedioxy)propyl]-3,4-(dimethylmethylenedioxy)-2-hydroxy-3-(methylthio)carbonylpentanoate

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Chemical Property of ethyl [2R,2(1R,2S),3S,4R]-5-benzyloxy-2-[3-benzyloxy-1,2-(diethylmethylenedioxy)propyl]-3,4-(dimethylmethylenedioxy)-2-hydroxy-3-(methylthio)carbonylpentanoate

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Technology Process of ethyl [2R,2(1R,2S),3S,4R]-5-benzyloxy-2-[3-benzyloxy-1,2-(diethylmethylenedioxy)propyl]-3,4-(dimethylmethylenedioxy)-2-hydroxy-3-(methylthio)carbonylpentanoate

There total 6 articles about ethyl [2R,2(1R,2S),3S,4R]-5-benzyloxy-2-[3-benzyloxy-1,2-(diethylmethylenedioxy)propyl]-3,4-(dimethylmethylenedioxy)-2-hydroxy-3-(methylthio)carbonylpentanoate 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: 40.0%

: ((4R,5S)-5-Benzyloxymethyl-2,2-diethyl-[1,3]dioxolan-4-yl)-oxo-acetic acid ethyl ester

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

: 191935-18-9
ethyl [2S,2(1R,2S),3S,4R]-5-benzyloxy-2-[3-benzyloxy-1,2-(diethylmethylenedioxy)propyl]-3,4-(dimethylmethylenedioxy)-2-hydroxy-3-(methylthio)carbonylpentanoate

: 871514-48-6
ethyl [2R,2(1R,2S),3S,4R]-5-benzyloxy-2-[3-benzyloxy-1,2-(diethylmethylenedioxy)propyl]-3,4-(dimethylmethylenedioxy)-2-hydroxy-3-(methylthio)carbonylpentanoate

Guidance literature:: With tin(II) trifluoromethanesulfonate; In various solvent(s); at -70 ℃; for 1.5h;
DOI:10.1016/j.tet.2005.09.030

Reference yield:

: 81801-09-4
4-O-benzyl-2,3-O-isopropylidene-D-threose

: 871514-48-6
ethyl [2R,2(1R,2S),3S,4R]-5-benzyloxy-2-[3-benzyloxy-1,2-(diethylmethylenedioxy)propyl]-3,4-(dimethylmethylenedioxy)-2-hydroxy-3-(methylthio)carbonylpentanoate

Guidance literature:: Multi-step reaction with 5 steps

1.1: 95 percent / 2-methyl-2-butene; NaH₂PO₄; NaClO₂ / 2-methyl-propan-2-ol; H₂O / 18 h / 20 °C

2.1: oxalyl chloride; DMF / CH₂Cl₂ / 1.5 h / 20 °C

3.1: 77 percent / n-Bu₄NI / CH₂Cl₂; H₂O / 0.17 h / 0 °C

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

4.2: 95 percent / tetrahydrofuran; hexane / -78 - 20 °C

5.1: 39 percent / Sn(OTf)2 / various solvent(s) / 1.5 h / -70 °C

With sodium chlorite; sodium dihydrogenphosphate; tin(II) trifluoromethanesulfonate; n-butyllithium; 2-methyl-but-2-ene; oxalyl dichloride; tetra-(n-butyl)ammonium iodide; N,N-dimethyl-formamide; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; hexane; dichloromethane; water; tert-butyl alcohol; 5.1: aldol coupling;
DOI:10.1016/j.tet.2005.09.030

Reference yield:

: 871514-33-9
S-methyl (2S,3R)-4-benzyloxy-2,3-(dimethylmethylenedioxy)butanethioate

: 871514-48-6
ethyl [2R,2(1R,2S),3S,4R]-5-benzyloxy-2-[3-benzyloxy-1,2-(diethylmethylenedioxy)propyl]-3,4-(dimethylmethylenedioxy)-2-hydroxy-3-(methylthio)carbonylpentanoate

Guidance literature:: Multi-step reaction with 2 steps

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

1.2: 95 percent / tetrahydrofuran; hexane / -78 - 20 °C

2.1: 39 percent / Sn(OTf)2 / various solvent(s) / 1.5 h / -70 °C

With tin(II) trifluoromethanesulfonate; n-butyllithium; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; hexane; 2.1: aldol coupling;
DOI:10.1016/j.tet.2005.09.030