143216-82-4

Usage

Uses

Used in Organic Synthesis:
(3beta,4alpha,17Z)-3,4-bis[tert-butyl(dimethyl)silyl]oxy-N-methoxygona-1,5(10),6,8,11,13-hexaen-17-imine is used as a reagent in organic synthesis for its unique structure and functional groups, which can be utilized in various chemical reactions to form new compounds.
Used in Chemical Reactions:
This complex organic compound is used as a reagent in chemical reactions due to its imine functional group and silicon-containing groups, which can participate in a variety of reactions to produce desired products.
Used in Biochemical Research:
(3beta,4alpha,17Z)-3,4-bis[tert-butyl(dimethyl)silyl]oxy-N-methoxygona-1,5(10),6,8,11,13-hexaen-17-imine is used in biochemical research for its potential applications in studying complex biological systems and interactions, given its unique structure and functional groups.
Used in Material Science:
This chemical is used in material science for its potential applications in the development of new materials with specific properties, such as those with unique electronic, optical, or mechanical characteristics, due to its complex structure and composition.

Upstream product

• 17521-83-4 3-methoxy-6,7,16,17-tetrahydro-15H-cyclopenta-phenanthren-17-one 
• 143216-80-2 15,16-dihydrocyclopentaphenanthren-3,4,17-trione 17-methoxime 
• 143216-79-9 15,16-dihydro-3-hydroxycyclopentaphenanthren-17-one methoxime 
• 792-07-4 3-methoxy-16,17-dihydro-15H-cyclopenta-phenanthren-17-one 
• 69739-34-0 t-butyldimethylsiyl triflate 
• 143216-81-3 (3S,4S)-3,4-Dihydroxy-3,4,15,16-tetrahydro-cyclopenta[a]phenanthren-17-one O-methyl-oxime 
• 24684-50-2 15,16-dihydro-3-hydroxycyclopentaphenanthren-17-one 

Downstream Products

• 143216-84-6 (+/-)-2α-bromo-1,2,3,4,15,16-hexahydro-trans-1β,3α,4β-trihydroxycyclopentaphenanthren-17-one 
• 143290-36-2 3,4,15,16-tetrahydro-trans-3,4-dihydroxycyclopentaphenanthren-17-one 
• 143216-83-5 3,4,15,16-tetrahydro-trans-3,4-bis<(tert-butyldimethylsilyl)oxy>cyclopentaphenanthren-17-one 

Relevant academic research and scientific papers

Synthesis of the Putative Active Metabolites of the Cyclopentaphenanthrenes. Synthesis of the trans-3,4-Dihydro 3,4-Diol and syn-3,4-Diol 1,2-Epoxide Derivatives of the Mutagen 15,16-Dihydrocyclopentaphenanthren-17-one

The first synthesis of the trans-dihydro diol and syn-diol epoxide derivatives of a biologically active cyclopentaphenanthrene is described.The cyclopentaphenanthrene skeleton is rapidly and efficiently assembled utilizing the Lewis acid-catalyzed Diels-Alder reaction of 1,2-dihydro-7-methoxy-4-vinylnaphthalene (5) with an α-heterosubstituted cyclopentenone, a "cyclopentynone" equivalent.It was found that the Diels-Alder reaction of α-(phenylselenenyl)- (6a) or α-bromocyclopentenone (6b) with 5 in the presence of 1.5 equiv of SnCl4 followed by elimination with hydrogen peroxide or DBU produced the key intermediate 15,16-dihydro-3-methoxycyclopentaphenanthren-17-one (10) in 28percent or 59percent overall yield, respectively.The synthesis of the A-ring metabolites features the use of a unique methoxime protecting group for the 17-ketone.The deprotection of the 17-methoxime group of the highly acid-sensitive 3,4-trans-dihydro 3,4-diol bis(TBDMS) ether 15b was achieved through the use of the low-valent titanium reagent produced upon reduction of TiCl3-3THF by DIBAL-H (51percent).Treatment of bis-(TBDMS) ether 16 with TBAF in THF provided the desired 3,4-trans-dihydro 3,4-diol (3) (83percent), thus achieving the synthesis of 3 in 10 steps in 9.6percent overall yield from 6b.In addition, the bay-region syn-3,4-diol 1,2-epoxide (4a) was also synthesized from 3 in two steps in 59percent overall yield.