[2R,4S,6S]-4-(propan-2-one)-6-[(2-triphenylmethyloxy)-ethyl]-2-phenyl-1,3-dioxane

Base Information

Chemical Name:[2R,4S,6S]-4-(propan-2-one)-6-[(2-triphenylmethyloxy)-ethyl]-2-phenyl-1,3-dioxane
CAS No.:187819-45-0
Molecular Formula:C₃₃H₃₂O₄
Molecular Weight:492.615
Hs Code.:

Synonyms:[2R,4S,6S]-4-(propan-2-one)-6-[(2-triphenylmethyloxy)-ethyl]-2-phenyl-1,3-dioxane

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Chemical Property of [2R,4S,6S]-4-(propan-2-one)-6-[(2-triphenylmethyloxy)-ethyl]-2-phenyl-1,3-dioxane

Chemical Property:

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Technology Process of [2R,4S,6S]-4-(propan-2-one)-6-[(2-triphenylmethyloxy)-ethyl]-2-phenyl-1,3-dioxane

There total 4 articles about [2R,4S,6S]-4-(propan-2-one)-6-[(2-triphenylmethyloxy)-ethyl]-2-phenyl-1,3-dioxane 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: 81.0%

: 917-54-4
methyllithium

: 203454-75-5
[2R,4S,6S]-4-(N-methoxy-N-methyl-carboxamidomethyl)-6-[(triphenylmethyloxy)methyl]-2-phenyl-1,3-dioxane

: 187819-45-0
[2R,4S,6S]-4-(propan-2-one)-6-[(2-triphenylmethyloxy)-ethyl]-2-phenyl-1,3-dioxane

Guidance literature:: In tetrahydrofuran; at -78 ℃;
DOI:10.1002/anie.199727381

Reference yield:

: 65291-30-7
(R)-(+)-trityl glycidyl ether

: 187819-45-0
[2R,4S,6S]-4-(propan-2-one)-6-[(2-triphenylmethyloxy)-ethyl]-2-phenyl-1,3-dioxane

Guidance literature:: Multi-step reaction with 4 steps

1.1: CuI / tetrahydrofuran / 1 h / -78 °C

1.2: 32.54 g / tetrahydrofuran / 1.5 h / -78 °C

2.1: O₃ / CH₂Cl₂ / 0.67 h / -78 °C

2.2: PPh₃ / CH₂Cl₂ / 5 h / 20 °C

2.3: 73 percent / CH₂Cl₂ / 14 h / 20 °C

3.1: 76 percent / t-BuOK / tetrahydrofuran / 2.5 h / 0 °C

4.1: 81 percent / diethyl ether / 1.5 h / -78 °C

With copper(l) iodide; potassium tert-butylate; ozone; In tetrahydrofuran; diethyl ether; dichloromethane; 1.1: Metallation / 1.2: Condensation / 2.1: Oxidation / 2.2: Reduction / 2.3: Condensation / 3.1: Addition / 4.1: Methylation;
DOI:10.1016/S0040-4020(99)00438-X

Reference yield:

: 203454-71-1
[2R]-1-triphenylmethoxy-2-hydroxy-4-pentene

: 187819-45-0
[2R,4S,6S]-4-(propan-2-one)-6-[(2-triphenylmethyloxy)-ethyl]-2-phenyl-1,3-dioxane

Guidance literature:: Multi-step reaction with 3 steps

1.1: O₃ / CH₂Cl₂ / 0.67 h / -78 °C

1.2: PPh₃ / CH₂Cl₂ / 5 h / 20 °C

1.3: 73 percent / CH₂Cl₂ / 14 h / 20 °C

2.1: 76 percent / t-BuOK / tetrahydrofuran / 2.5 h / 0 °C

3.1: 81 percent / diethyl ether / 1.5 h / -78 °C

With potassium tert-butylate; ozone; In tetrahydrofuran; diethyl ether; dichloromethane; 1.1: Oxidation / 1.2: Reduction / 1.3: Condensation / 2.1: Addition / 3.1: Methylation;
DOI:10.1016/S0040-4020(99)00438-X