203174-51-0

Basic information

• Product Name: (E)-(1S,3S)-3-(tert-Butyl-diphenyl-silanyl)-4-methyl-1-phenyl-hex-4-en-1-ol
• Synonyms: (E)-(1S,3S)-3-(tert-Butyl-diphenyl-silanyl)-4-methyl-1-phenyl-hex-4-en-1-ol
• CAS NO: 203174-51-0
• Molecular Weight: 428.69
• Mol File: 203174-51-0.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (E)-(1S,3S)-3-(tert-Butyl-diphenyl-silanyl)-4-methyl-1-phenyl-hex-4-en-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-(1S,3S)-3-(tert-Butyl-diphenyl-silanyl)-4-methyl-1-phenyl-hex-4-en-1-ol(203174-51-0)
• EPA Substance Registry System: (E)-(1S,3S)-3-(tert-Butyl-diphenyl-silanyl)-4-methyl-1-phenyl-hex-4-en-1-ol(203174-51-0)

Safety Data

• Hazardous Substances Data: 203174-51-0(Hazardous Substances Data)

Upstream product

• 203174-47-4 (E)-(S)-4-Methyl-1-phenyl-3-phenylsulfanyl-hex-4-en-1-ol 
• 497-02-9 (E)-2-methyl-2-buten-1-ol 
• 28127-58-4 sec-butyl tiglate 
• 203174-49-6 tert-Butyl-((E)-(S)-4-methyl-1-phenyl-3-phenylsulfanyl-hex-4-enyloxy)-diphenyl-silane 

Downstream Products

• 203174-61-2 (2S,4S,5S,6S)-4-(tert-Butyl-diphenyl-silanyl)-5,6-dimethyl-2-phenyl-tetrahydro-pyran-2-ol 
• 203174-70-3 tert-Butyl-phenyl-((2S,3S,4R,5S,6S)-2,3,5-trimethyl-6-phenyl-tetrahydro-pyran-4-yl)-silanol 
• 203174-55-4 (S)-2-((2S,3S,4S,5S)-2-tert-Butyl-4,5-dimethyl-2-phenyl-[1,2]oxasilolan-3-yl)-1-phenyl-ethanol 
• 203174-67-8 2-((2S,3S,4S,5S)-2-tert-Butyl-4,5-dimethyl-2-phenyl-[1,2]oxasilolan-3-yl)-1-phenyl-ethanone 
• 203174-53-2 (1S,3S,4S,5S)-3-(tert-Butyl-diphenyl-silanyl)-4-methyl-1-phenyl-hexane-1,5-diol 

Relevant articles and documents

Approaching the C33-C38 fragments of amphotericin B and nystatin by a retro-[1,4]-Brook rearrangement and the stereoselective manipulation of the resulting allylsilane

Sulfide S-4 (98.6% ee) furnished allylsilane S,S-anti-2 through a potassium naphthalenide induced, highly stereoselective retro-Brook rearrangement. Treatment with diethylborane followed by NaOOH/H2O2 delivered alcohol 9 as a single diastereomer. Cylization (→10), oxidation (→16), and methylation gave ketone 17. Reduction of 17 with Et3SiH in CF3CO2H was accompanied by an unprecedented rearrangement of the neighboring oxasilolane ring to the C-silylated tetrahydropyran 20. It was oxidized to alcohol 21 which - if one inverted its OH group - would become a new C33-C38 building block for the polyol/polyene antibiotics amphotericin B and nystatin.