51092-15-0

Upstream product

• 876908-23-5 (25R)-2α,3α-epoxy-5-hydroxy-5β-spirostan-6-one 
• 56786-63-1 (25R)-3β,5-dihydroxy-5α-spirostan-6-one 
• 876908-18-8 (25R)-3β-(t-butyldimethylsilyloxy)-5α-spirostane-5,6β-diol 
• 876908-20-2 (25R)-3β,5-dihydroxy-5β-spirostan-6-one 
• 321857-67-4 (25R)-5-hydroxy-5α-spirostan-6-one 
• 56816-69-4 (25R)-spirostan-22α-O-3β,5α,6β-triol 
• 523981-69-3 (25R)-3α,5-cyclo-5α-spirostan-6β-ol 
• 200353-19-1 (25R)-5-hydroxy-5β-spirost-2-en-6-one 
• 16653-41-1 trigonegenin B 
• 127128-79-4 (25R)-3α,5-cyclo-5α-spirostan-6-one 

Relevant academic research and scientific papers

Novel 5β-hydroxyspirostan-6-ones ecdysteroid antagonists: Synthesis and biological testing

Eight new 5β-hydroxy-spirostan-6-ones bearing hydroxy and amino functions in the A ring, i.e., 3β-OH, 3α-OH, 2β,3β-OH, 2α,3β-OH, 3β-NH2, 2α-NH2-3β-OH, 2β-NH2-3β-OH, and 2β-OH-3β-NH2, were efficiently synthesized, and their antiecdysteroid activities were evaluated on the metamorphosis bioassay of mosquito Aedes aegypti. To our knowledge, these new steroids represent the first 5β-hydroxy-spirostanes which have been tested for antiecdysteroid activity in mosquitoes. The higher antagonistic effect was found for compounds bearing the 3β-hydroxy and 2β,3β-dihydroxy functionality, which show promise as environmental friendly insecticides.

The preparation of the spirostanic analogues of brassinolide and castasterone

Methods for the preparation of the spirostanic analogues of brassinosteroids (25R)-5α-spirostan-6-one-2α,3α-diol and (25R)-B-homo-5α-spirostan-6-oxo-7-oxalactone-2α,3α-diol, starting from diosgenin, were examined. The best preparative route was via diosgenin tosylation, isosteroidal rearrangement with potassium acetate in aqueous acetone, oxidation with Jones reagent, cyclopropyl ring opening with hydrobromic acid, hydrogen bromide elimination with lithium bromide and carbonate, dihydroxylation with osmium tetroxide and N-methylmorpholine N-oxide, producing (25R)-5α-spirostan-6-one-2α,3α-diol in 57.3% overall yield and lactonization with trifluoroperoxyacetic acid producing (25R)-B-homo-5α-spirostan-6-oxo-7-oxalactone-2α,3α-diol in 24.6% overall yield from diosgenin. The shortest route to (25R)-5α-spirostan-6-one-2α,3α-diol results in only 39.4% overall yield.

Synthesis of spirostanic analogues of brassinosteroids via homogeneous permanganate dihydroxylation

Homogeneous non-aqueous permanganate dihydroxylation is used to synthesize spirostanic analogues of brassinosteroids bearing a variety of oxygen functions on ring B.