(2R,3R,4S,7S)-7-(3-(tert-butyldimethylsilyloxy)phenyl)-3-hydroxy-7-methoxy-2,4-dimethylheptanal

Base Information

Chemical Name:(2R,3R,4S,7S)-7-(3-(tert-butyldimethylsilyloxy)phenyl)-3-hydroxy-7-methoxy-2,4-dimethylheptanal
CAS No.:1450899-53-2
Molecular Formula:C₂₂H₃₈O₄Si
Molecular Weight:394.627
Hs Code.:

Synonyms:(2R,3R,4S,7S)-7-(3-(tert-butyldimethylsilyloxy)phenyl)-3-hydroxy-7-methoxy-2,4-dimethylheptanal

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Chemical Property of (2R,3R,4S,7S)-7-(3-(tert-butyldimethylsilyloxy)phenyl)-3-hydroxy-7-methoxy-2,4-dimethylheptanal

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Technology Process of (2R,3R,4S,7S)-7-(3-(tert-butyldimethylsilyloxy)phenyl)-3-hydroxy-7-methoxy-2,4-dimethylheptanal

There total 8 articles about (2R,3R,4S,7S)-7-(3-(tert-butyldimethylsilyloxy)phenyl)-3-hydroxy-7-methoxy-2,4-dimethylheptanal 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: 48.0%

: 1450899-51-0
(2S,5S)-5-(3-(tert-butyldimethylsilyloxy)phenyl)-5-methoxy-2-methylpentanal

: 123-38-6
propionaldehyde

: 1450899-53-2
(2R,3R,4S,7S)-7-(3-(tert-butyldimethylsilyloxy)phenyl)-3-hydroxy-7-methoxy-2,4-dimethylheptanal

Guidance literature:: With D-Prolin; In N,N-dimethyl-formamide; at 2 ℃; for 48h; stereoselective reaction; Inert atmosphere;
DOI:10.1021/jo401248n

Reference yield:

: 1-(3-((tert-butyldimethylsilyl)oxy)phenyl)prop-2-en-1-ol

: 1450899-53-2
(2R,3R,4S,7S)-7-(3-(tert-butyldimethylsilyloxy)phenyl)-3-hydroxy-7-methoxy-2,4-dimethylheptanal

Guidance literature:: Multi-step reaction with 7 steps

1.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide; dichloromethane / 3.08 h / 0 - 20 °C / Inert atmosphere

2.1: titanium tetrachloride; titanium(IV) isopropylate; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.58 h / Inert atmosphere

2.2: 0.58 h / -5 °C / Inert atmosphere

3.1: dimethylsulfide borane complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / dichloromethane; toluene / 5 h / -5 - 0 °C / Inert atmosphere

4.1: 2,6-di-tert-butyl-pyridine / dichloromethane / 18.08 h / 0 - 20 °C / Inert atmosphere

5.1: sodium tetrahydroborate / tetrahydrofuran; water / 14 h / 20 °C

6.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide; dichloromethane / 3.08 h / 0 - 20 °C / Inert atmosphere

7.1: D-Prolin / N,N-dimethyl-formamide / 48 h / 2 °C / Inert atmosphere

With titanium(IV) isopropylate; sodium tetrahydroborate; 2,6-di-tert-butyl-pyridine; dimethylsulfide borane complex; titanium tetrachloride; N-ethyl-N,N-diisopropylamine; D-Prolin; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo401248n

Reference yield:

: 1450899-48-5
(R)-4-benzyl-3-((2S,5S)-5-(3-(tert-butyldimethylsilyloxy)-phenyl)-5-hydroxy-2-methylpentanoyl)oxazolidin-2-one

: 1450899-53-2
(2R,3R,4S,7S)-7-(3-(tert-butyldimethylsilyloxy)phenyl)-3-hydroxy-7-methoxy-2,4-dimethylheptanal

Guidance literature:: Multi-step reaction with 4 steps

1: 2,6-di-tert-butyl-pyridine / dichloromethane / 18.08 h / 0 - 20 °C / Inert atmosphere

2: sodium tetrahydroborate / tetrahydrofuran; water / 14 h / 20 °C

3: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide; dichloromethane / 3.08 h / 0 - 20 °C / Inert atmosphere

4: D-Prolin / N,N-dimethyl-formamide / 48 h / 2 °C / Inert atmosphere

With sodium tetrahydroborate; 2,6-di-tert-butyl-pyridine; D-Prolin; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1021/jo401248n