(2R,3S)-3-[(S)-1-(tert-butyldimethylsiloxy)ethyl]-2,3-(isopropylidenedioxy)-4-oxo-4-phenylbutanal

Base Information

Chemical Name:(2R,3S)-3-[(S)-1-(tert-butyldimethylsiloxy)ethyl]-2,3-(isopropylidenedioxy)-4-oxo-4-phenylbutanal
CAS No.:1449307-12-3
Molecular Formula:C₂₁H₃₂O₅Si
Molecular Weight:392.568
Hs Code.:

Synonyms:(2R,3S)-3-[(S)-1-(tert-butyldimethylsiloxy)ethyl]-2,3-(isopropylidenedioxy)-4-oxo-4-phenylbutanal

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Chemical Property of (2R,3S)-3-[(S)-1-(tert-butyldimethylsiloxy)ethyl]-2,3-(isopropylidenedioxy)-4-oxo-4-phenylbutanal

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Technology Process of (2R,3S)-3-[(S)-1-(tert-butyldimethylsiloxy)ethyl]-2,3-(isopropylidenedioxy)-4-oxo-4-phenylbutanal

There total 7 articles about (2R,3S)-3-[(S)-1-(tert-butyldimethylsiloxy)ethyl]-2,3-(isopropylidenedioxy)-4-oxo-4-phenylbutanal 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:

: C₃₁H₅₂O₆Si

: 1449307-12-3
(2R,3S)-3-[(S)-1-(tert-butyldimethylsiloxy)ethyl]-2,3-(isopropylidenedioxy)-4-oxo-4-phenylbutanal

Guidance literature:: With toluene-4-sulfonic acid; at 20 ℃; for 1.5h; Inert atmosphere;
DOI:10.1016/j.tet.2013.05.091

Reference yield:

: 1449307-00-9
(3S,4R,5R)-3-[(S)-1-hydroxyethyl]-5-{(1R,2S,5R)-[2-isopropyl-5-methylcyclohexyl]oxy}-3,4-(isopropylidenedioxy)-4,5-dihydro-3H-furan-2-one

: 1449307-12-3
(2R,3S)-3-[(S)-1-(tert-butyldimethylsiloxy)ethyl]-2,3-(isopropylidenedioxy)-4-oxo-4-phenylbutanal

Guidance literature:: Multi-step reaction with 3 steps

1: triethylamine / dichloromethane / 2.5 h / 0 - 20 °C / Inert atmosphere

2: lithium chloride / tetrahydrofuran; dibutyl ether / 0.17 h / -10 °C / Inert atmosphere

3: toluene-4-sulfonic acid / 1.5 h / 20 °C / Inert atmosphere

With toluene-4-sulfonic acid; triethylamine; lithium chloride; In tetrahydrofuran; dichloromethane; dibutyl ether;
DOI:10.1016/j.tet.2013.05.091

Reference yield:

: 1449307-33-8
C₁₇H₂₈O₅

: 1449307-12-3
(2R,3S)-3-[(S)-1-(tert-butyldimethylsiloxy)ethyl]-2,3-(isopropylidenedioxy)-4-oxo-4-phenylbutanal

Guidance literature:: Multi-step reaction with 5 steps

1.1: lithium diisopropyl amide / tetrahydrofuran / 0.08 h / -78 °C / Inert atmosphere

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

2.1: trimethyl(benzyl)ammonium fluoride / tetrahydrofuran / 2.3 h / -78 - -10 °C / Molecular sieve; Inert atmosphere

3.1: triethylamine / dichloromethane / 2.5 h / 0 - 20 °C / Inert atmosphere

4.1: lithium chloride / tetrahydrofuran; dibutyl ether / 0.17 h / -10 °C / Inert atmosphere

5.1: toluene-4-sulfonic acid / 1.5 h / 20 °C / Inert atmosphere

With trimethyl(benzyl)ammonium fluoride; toluene-4-sulfonic acid; triethylamine; lithium chloride; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; dibutyl ether;
DOI:10.1016/j.tet.2013.05.091