(2S,3R,4R,5S)-4-(dimethyl(phenyl)silyl)-5-(methoxymethyl)-2-phenyltetrahydrofuran-3-carboxaldehyde

Base Information

Chemical Name:(2S,3R,4R,5S)-4-(dimethyl(phenyl)silyl)-5-(methoxymethyl)-2-phenyltetrahydrofuran-3-carboxaldehyde
CAS No.:1261974-81-5
Molecular Formula:C₂₁H₂₆O₃Si
Molecular Weight:354.521
Hs Code.:

Synonyms:(2S,3R,4R,5S)-4-(dimethyl(phenyl)silyl)-5-(methoxymethyl)-2-phenyltetrahydrofuran-3-carboxaldehyde

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Chemical Property of (2S,3R,4R,5S)-4-(dimethyl(phenyl)silyl)-5-(methoxymethyl)-2-phenyltetrahydrofuran-3-carboxaldehyde

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Technology Process of (2S,3R,4R,5S)-4-(dimethyl(phenyl)silyl)-5-(methoxymethyl)-2-phenyltetrahydrofuran-3-carboxaldehyde

There total 3 articles about (2S,3R,4R,5S)-4-(dimethyl(phenyl)silyl)-5-(methoxymethyl)-2-phenyltetrahydrofuran-3-carboxaldehyde 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: 90.0%

: 1261974-82-6
(2S,3R,Z)-3-(dimethyl(phenyl)silyl)-5-ethoxy-1-methoxypent-4-en-2-ol

: 100-52-7
benzaldehyde

: 1261974-81-5
(2S,3R,4R,5S)-4-(dimethyl(phenyl)silyl)-5-(methoxymethyl)-2-phenyltetrahydrofuran-3-carboxaldehyde

Guidance literature:: With toluene-4-sulfonic acid; In dichloromethane; at 0 ℃; for 0.166667h; stereoselective reaction;
DOI:10.1021/ol102848w

Reference yield:

: 1261974-99-5
(2S,3R)-3-(dimethyl(phenyl)silyl)-5-ethoxy-1-methoxypent-4-yn-2-ol

: 1261974-81-5
(2S,3R,4R,5S)-4-(dimethyl(phenyl)silyl)-5-(methoxymethyl)-2-phenyltetrahydrofuran-3-carboxaldehyde

Guidance literature:: Multi-step reaction with 2 steps

1: pyridine; Lindlar's catalyst; hydrogen / ethyl acetate / 1 h

2: toluene-4-sulfonic acid / dichloromethane / 0.17 h / 0 °C

With pyridine; Lindlar's catalyst; hydrogen; toluene-4-sulfonic acid; In dichloromethane; ethyl acetate; 2: Mukaiyama reaction;
DOI:10.1021/ol102848w

Reference yield:

: C₁₂H₁₈O₂Si

: 1261974-81-5
(2S,3R,4R,5S)-4-(dimethyl(phenyl)silyl)-5-(methoxymethyl)-2-phenyltetrahydrofuran-3-carboxaldehyde

Guidance literature:: Multi-step reaction with 3 steps

1.1: n-butyllithium / diethyl ether; hexane / 1 h / -78 °C / Inert atmosphere

1.2: 0.5 h / -78 °C / Inert atmosphere

1.3: 0.25 h / -78 - 20 °C / Inert atmosphere

2.1: pyridine; Lindlar's catalyst; hydrogen / ethyl acetate / 1 h

3.1: toluene-4-sulfonic acid / dichloromethane / 0.17 h / 0 °C

With pyridine; n-butyllithium; Lindlar's catalyst; hydrogen; toluene-4-sulfonic acid; In diethyl ether; hexane; dichloromethane; ethyl acetate; 3.1: Mukaiyama reaction;
DOI:10.1021/ol102848w