ethyl (3R)-2-acetoxy-3-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]butanoate

Base Information

Chemical Name:ethyl (3R)-2-acetoxy-3-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]butanoate
CAS No.:866343-47-7
Molecular Formula:C₁₉H₂₆O₆
Molecular Weight:350.412
Hs Code.:

Synonyms:ethyl (3R)-2-acetoxy-3-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]butanoate

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Chemical Property of ethyl (3R)-2-acetoxy-3-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]butanoate

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Technology Process of ethyl (3R)-2-acetoxy-3-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]butanoate

There total 1 articles about ethyl (3R)-2-acetoxy-3-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]butanoate 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:

: lead(IV) acetate

: 326603-47-8
ethyl (3S)-3-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]butanoate

: 866343-47-7
ethyl (3R)-2-acetoxy-3-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]butanoate

Guidance literature:: ethyl (3S)-3-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]butanoate; With chloro-trimethyl-silane; In tetrahydrofuran; at -78 - 20 ℃;

lead(IV) acetate; In dichloromethane; at -78 - 20 ℃; Further stages.;
DOI:10.1055/s-2007-1000868

Reference yield: 72.0%

: 866343-47-7
ethyl (3R)-2-acetoxy-3-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]butanoate

: 866343-55-7
ethyl (2S,3R)-3-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]-2-hydroxybutanoate

: 866343-42-2
ethyl (2R,3R)-3-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]-2-hydroxybutanoate

Guidance literature:: With sodium ethanolate; In ethanol; at 20 ℃;
DOI:10.1002/chem.200500282

Reference yield:

: 866343-47-7
ethyl (3R)-2-acetoxy-3-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]butanoate

: tert-butyl (5R,6,S,E)-6-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]-5-hydroxyhept-2-enoate

Guidance literature:: Multi-step reaction with 8 steps

1.1: NaOEt / ethanol / 20 °C

2.1: NaH / 1,2-dimethoxy-ethane

2.2: 89 percent / 1,2-dimethoxy-ethane / 2 h / 20 - 60 °C

3.1: 98 percent / LiAlH₄ / tetrahydrofuran / 5 - 20 °C

4.1: 91 percent / DABCO / CH₂Cl₂ / 0 - 20 °C

5.1: 98 percent / NaHCO₃ / dimethylsulfoxide / 43 h / 60 - 80 °C

6.1: 91 percent / DIBALH / toluene / 2 h / -78 °C

7.1: NaH / tetrahydrofuran / 0 - 20 °C

7.2: 83 percent / tetrahydrofuran / 3 h / -78 °C

8.1: 100 percent / p-toluenesulfinic acid / [Pd(PPh₃)4] / CH₂Cl₂ / 1.5 h / 20 °C

With 1,4-diaza-bicyclo[2.2.2]octane; lithium aluminium tetrahydride; p-toluene sulfinic acid; sodium ethanolate; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; 1,2-dimethoxyethane; ethanol; dichloromethane; dimethyl sulfoxide; toluene; 7.2: Horner-Wadsworth-Emmons reaction;
DOI:10.1002/chem.200500282