(2S,4S,5S)-5-<(tert-Butyldiphenylsilyl)oxy>-7-dibromo-2,4-dimethyl-6-heptenal

Base Information

Chemical Name:(2S,4S,5S)-5-<(tert-Butyldiphenylsilyl)oxy>-7-dibromo-2,4-dimethyl-6-heptenal
CAS No.:147121-99-1
Molecular Formula:C₂₅H₃₂Br₂O₂Si
Molecular Weight:552.421
Hs Code.:

Synonyms:(2S,4S,5S)-5-<(tert-Butyldiphenylsilyl)oxy>-7-dibromo-2,4-dimethyl-6-heptenal

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Chemical Property of (2S,4S,5S)-5-<(tert-Butyldiphenylsilyl)oxy>-7-dibromo-2,4-dimethyl-6-heptenal

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Technology Process of (2S,4S,5S)-5-<(tert-Butyldiphenylsilyl)oxy>-7-dibromo-2,4-dimethyl-6-heptenal

There total 6 articles about (2S,4S,5S)-5-<(tert-Butyldiphenylsilyl)oxy>-7-dibromo-2,4-dimethyl-6-heptenal 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: 57.0%

: 147121-98-0
(2'S,4S,4'S,5'S)-3-<5'-<(tert-Butyldiphenylsilyl)oxy>-7'-dibromo-2',4'-dimethylhept-6'-enoyl>-4-isopropyl-1,3-oxazolidin-2-one

: 147122-19-8
(2S,4S,5S)-5-<(tert-Butyldiphenylsilyl)oxy>-7-dibromo-2,4-dimethyl-6-heptenol

: 147121-99-1
(2S,4S,5S)-5-<(tert-Butyldiphenylsilyl)oxy>-7-dibromo-2,4-dimethyl-6-heptenal

Guidance literature:: With diisobutylaluminium hydride; In dichloromethane; -78 to -10 deg C, then 16 h;
DOI:10.1021/jo00060a036

Reference yield:

: 147122-17-6
(S)-3-[(2S,4S,5S,6R)-5-(tert-Butyl-diphenyl-silanyloxy)-6,7-dihydroxy-2,4-dimethyl-heptanoyl]-4-isopropyl-oxazolidin-2-one

: 147121-99-1
(2S,4S,5S)-5-<(tert-Butyldiphenylsilyl)oxy>-7-dibromo-2,4-dimethyl-6-heptenal

Guidance literature:: Multi-step reaction with 4 steps

1: NaIO₄ / H₂O; tetrahydrofuran / 16 h / 25 °C

2: PPh₃ / CH₂Cl₂ / 0.5 h / 0 °C

3: 34 percent / DIBAL-H / CH₂Cl₂ / -50 to -10 deg C, then 16 h

4: 1) oxalyl chloride, DMSO, 2) NEt₃ / 1) CH₂Cl₂, -78 deg C, 30 min, 2) to 25 deg C over 1 h

With sodium periodate; oxalyl dichloride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane; water;
DOI:10.1021/jo00060a036

Reference yield:

: 147122-18-7
(2S,3S,5S)-2-(tert-Butyl-diphenyl-silanyloxy)-6-((S)-4-isopropyl-2-oxo-oxazolidin-3-yl)-3,5-dimethyl-6-oxo-hexanal

: 147121-99-1
(2S,4S,5S)-5-<(tert-Butyldiphenylsilyl)oxy>-7-dibromo-2,4-dimethyl-6-heptenal

Guidance literature:: Multi-step reaction with 3 steps

1: PPh₃ / CH₂Cl₂ / 0.5 h / 0 °C

2: 34 percent / DIBAL-H / CH₂Cl₂ / -50 to -10 deg C, then 16 h

3: 1) oxalyl chloride, DMSO, 2) NEt₃ / 1) CH₂Cl₂, -78 deg C, 30 min, 2) to 25 deg C over 1 h

With oxalyl dichloride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; triphenylphosphine; In dichloromethane;
DOI:10.1021/jo00060a036