(2S,3S)-3--2-<(tert-butyldimethylsilyl)oxy>-4-phenylbutanal

Base Information

Chemical Name:(2S,3S)-3--2-<(tert-butyldimethylsilyl)oxy>-4-phenylbutanal
CAS No.:144944-04-7
Molecular Formula:C₂₁H₃₅NO₄Si
Molecular Weight:393.599
Hs Code.:

(2S,3S)-3-<N-(tert-butoxycarbonyl)amino>-2-<(tert-butyldimethylsilyl)oxy>-4-phenylbutanal

Synonyms:(2S,3S)-3--2-<(tert-butyldimethylsilyl)oxy>-4-phenylbutanal

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (2S,3S)-3--2-<(tert-butyldimethylsilyl)oxy>-4-phenylbutanal

Chemical Property:

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Technology Process of (2S,3S)-3--2-<(tert-butyldimethylsilyl)oxy>-4-phenylbutanal

There total 20 articles about (2S,3S)-3--2-<(tert-butyldimethylsilyl)oxy>-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: 84.0%

: 1174892-46-6
tert-butyl (2S,3S)-3-(tert-butyldimethylsilyloxy)-4-hydroxy-1-phenylbutan-2-ylcarbamate

: 144944-04-7
(2S,3S)-3--2-<(tert-butyldimethylsilyl)oxy>-4-phenylbutanal

Guidance literature:: With sodium carbonate; Dess-Martin periodane; In dichloromethane; at 20 ℃; for 2h;
DOI:10.1021/ml3000148

Reference yield:

: 229981-28-6
(3R,4S)-N-(tert-butoxycarbonyl)-4-amino-3-(tert-butyldimethylsilyloxy)-5-phenylpent-1-ene

: 144944-04-7
(2S,3S)-3--2-<(tert-butyldimethylsilyl)oxy>-4-phenylbutanal

Guidance literature:: (3R,4S)-N-(tert-butoxycarbonyl)-4-amino-3-(tert-butyldimethylsilyloxy)-5-phenylpent-1-ene; With ozone; In dichloromethane; at -78 ℃;

With oxygen; In dichloromethane; at -78 ℃;

With dimethylsulfide; In dichloromethane; at -78 - 23 ℃; for 4h;

Reference yield:

: 55177-35-0
(E)-4-phenyl-2-butenal

: 144944-04-7
(2S,3S)-3--2-<(tert-butyldimethylsilyl)oxy>-4-phenylbutanal

Guidance literature:: Multi-step reaction with 7 steps

1: 1.) 4 A MS / 1.) CH₂Cl₂, room temperature, 0.5 h, 2.) EtOAc, room temperature, 18 h

2: 92 percent / NBS / 1,2-dimethoxy-ethane; H₂O / 3 h / Ambient temperature

3: 97 percent / ethanol / 3 h / Ambient temperature

4: 97 percent / NaN₃, NH₄Cl / ethanol; H₂O / 360 h / Heating

5: 70 percent / H₂ / 5percent Pd on carbon / ethyl acetate / 17 h

6: 90 percent / 2,6-lutidine / CH₂Cl₂ / 4 h / -40 °C

7: 1.) DIBALH, 2.) SiO₂, oxalic acid / 1.) toluene, CH₂Cl₂, -78 deg C, 3 h, 2.) CH₂Cl₂, H₂O, room temperature, 20 h

With 2,6-dimethylpyridine; N-Bromosuccinimide; sodium azide; hydrogen; oxalic acid; silica gel; diisobutylaluminium hydride; ammonium chloride; palladium on activated charcoal; In 1,2-dimethoxyethane; ethanol; dichloromethane; water; ethyl acetate;
DOI:10.1021/jo962277g