(2R,3R,4E)-2-[[(1,1-dimethylethoxy)carbonyl]amino]-3-[3-[[(1,1-dimethylethyl)diphenylsilyl]oxy]propyl]-4-hexenoic acid

Base Information

Chemical Name:(2R,3R,4E)-2-[[(1,1-dimethylethoxy)carbonyl]amino]-3-[3-[[(1,1-dimethylethyl)diphenylsilyl]oxy]propyl]-4-hexenoic acid
CAS No.:264126-38-7
Molecular Formula:C₃₀H₄₃NO₅Si
Molecular Weight:525.761
Hs Code.:

Synonyms:(2R,3R,4E)-2-[[(1,1-dimethylethoxy)carbonyl]amino]-3-[3-[[(1,1-dimethylethyl)diphenylsilyl]oxy]propyl]-4-hexenoic acid

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Chemical Property of (2R,3R,4E)-2-[[(1,1-dimethylethoxy)carbonyl]amino]-3-[3-[[(1,1-dimethylethyl)diphenylsilyl]oxy]propyl]-4-hexenoic acid

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Technology Process of (2R,3R,4E)-2-[[(1,1-dimethylethoxy)carbonyl]amino]-3-[3-[[(1,1-dimethylethyl)diphenylsilyl]oxy]propyl]-4-hexenoic acid

There total 4 articles about (2R,3R,4E)-2-[[(1,1-dimethylethoxy)carbonyl]amino]-3-[3-[[(1,1-dimethylethyl)diphenylsilyl]oxy]propyl]-4-hexenoic acid 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: 87.0%

: 264126-37-6
N-[(1,1-dimethylethoxy)carbonyl]glycine (1R,2E)-6-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-2-hexenyl ester

: 264126-38-7
(2R,3R,4E)-2-[[(1,1-dimethylethoxy)carbonyl]amino]-3-[3-[[(1,1-dimethylethyl)diphenylsilyl]oxy]propyl]-4-hexenoic acid

Guidance literature:: With n-butyllithium; diisopropylamine; zinc(II) chloride; In tetrahydrofuran; at -78 - 20 ℃; for 9h;
DOI:10.1021/jo991293l

Reference yield:

: 127793-62-8
4-((tert-butyldiphenylsilyl)oxy)butanal

: 264126-38-7
(2R,3R,4E)-2-[[(1,1-dimethylethoxy)carbonyl]amino]-3-[3-[[(1,1-dimethylethyl)diphenylsilyl]oxy]propyl]-4-hexenoic acid

Guidance literature:: Multi-step reaction with 4 steps

1: 73 percent / Na₂CO₃ / dioxane; H₂O / 24 h / Thermolysis

2: 94 percent / (S)-2-methyl-CBS-oxazaborolidene; catecholborane / toluene / 6 h / -78 °C

3: 99 percent / DMAP; DIC / CH₂Cl₂ / 0 - 20 °C

4: 87 percent / n-BuLi; diisopropylamine; ZnCl₂ / tetrahydrofuran / 9 h / -78 - 20 °C

With dmap; n-butyllithium; sodium carbonate; dacarbazine; diisopropylamine; zinc(II) chloride; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; benzo[1,3,2]dioxaborole; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; toluene; 1: Condensation / 2: Reduction / 3: Condensation / 4: Rearrangement;
DOI:10.1021/jo991293l

Reference yield:

: 219916-37-7
(3E)-7-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-3-hepten-2-one

: 264126-38-7
(2R,3R,4E)-2-[[(1,1-dimethylethoxy)carbonyl]amino]-3-[3-[[(1,1-dimethylethyl)diphenylsilyl]oxy]propyl]-4-hexenoic acid

Guidance literature:: Multi-step reaction with 3 steps

1: 94 percent / (S)-2-methyl-CBS-oxazaborolidene; catecholborane / toluene / 6 h / -78 °C

2: 99 percent / DMAP; DIC / CH₂Cl₂ / 0 - 20 °C

3: 87 percent / n-BuLi; diisopropylamine; ZnCl₂ / tetrahydrofuran / 9 h / -78 - 20 °C

With dmap; n-butyllithium; dacarbazine; diisopropylamine; zinc(II) chloride; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; benzo[1,3,2]dioxaborole; In tetrahydrofuran; dichloromethane; toluene; 1: Reduction / 2: Condensation / 3: Rearrangement;
DOI:10.1021/jo991293l