85228-11-1

Upstream product

• 86678-41-3 (2R, 3S, 22R, 23R)-22,23-dihydroxy-2,3-isopropylidenedioxy-B-homo-7-oxa-5α-ergost-24(28)-en-6-one 
• 81481-13-2 (22E,24S)-2α,3α-Dihydroxy-5α-stigmast-22-en-6-one 2,3-acetonide 
• 93488-32-5 (2R, 3S, 6S, 7S, 24S, 22E)-6,7-epoxy-24-ethyl-7-hydroxy-2,3-isopropylidenedioxy-6-trimethylsilyloxy-5α-cholest-22-ene 
• 93488-30-3 (2R, 3S, 24S, 22E)-24-ethyl-2,3-isopropylidenedioxy-6-trimethylsilyloxy-5α-cholesta-6,22-diene 
• 87240-51-5 (2R, 3S, 24S, 22E)-24-ethyl-2,3-isopropylidenedioxy-7-oxa-B-homo-5α-cholest-22-en-6-one 
• 93344-80-0 C₃₅H₅₆O₈ 
• 86400-83-1 (22R,23R)-23-hydroxy-2α,3α-isopropylidenedioxy-22-methoxymethoxy-B-homo-7-oxa-5α-ergost-24(28)-en-6-one 
• 86400-81-9 (22R)-2α,3α-isopropylidenedioxy-22-methoxymethoxy-6-oxo-B-homo-24-nor-7-oxa-5α-cholan-22-al trimethylene dithioacetal 
• 85764-17-6 2α,3α,22-triacetoxy-B-homo-23,24-dinor-7-oxa-5α-cholan-6-one 
• 86400-82-0 (22R)-2α,3α-isopropylidenedioxy-22-methoxymethoxy-6-oxo-B-homo-24-nor-7-oxa-5α-cholan-23-al 
• 119850-42-9 (22R,23R,24R)-22,23-epoxy-2α,3α-isopropylidenedioxy-B-homo-7-oxa-5α-ergostan-6-one 
• 119829-51-5 (22E,24R)-2α,3α-isopropylidenedioxy-5α-ergost-22-en-6-one 
• 3152-46-3 (22E)-3α,5-cyclo-5α-ergosta-22-en-6-one 
• 72050-68-1 24R-methyl-5α-cholesta-2,22-dien-6-one 

Relevant academic research and scientific papers

A Novel Synthesis of Brassinolide and Related Compounds

A stereoselective synthesis of the natural promoting steroids, brassinolide, homobrassinolide, and typhasterol is described, which involves construction of a side chain by lactonisation of Z-(5) under acidid conditions to give an α,β-unsaturated δ-lactone (6) with the inversion of the configuration at C-22 of the epoxy steroid in quantitative yield.

SYNTHESIS OF NATURALLY OCCURRING BRASSINOSTEROIDS EMPLOYING CLEAVAGE OF 23,24-EPOXIDES AS KEY REACTIONS. SYNTHESIS OF BRASSINOLIDE, CASTASTERONE, DOLICHOLIDE, DOLICHOSTERONE, HOMODOLICHOLIDE, HOMODOLICHOSTERONE, 6-DEOXOCASTASTERONE AND 6-DEOXODOLICHOSTERONE

Eight new plant growth-promoting steroids (brassinolide, castasterone, dolicholide, dolichosterone, homodolicholide, homodolichosterone, 6-deoxocastasterone and 6-deoxodolichosterone) were synthesized by the regio- and stereoselective ring-opening reactions of 23,24-epoxides prepared from stigmasterol.

Stereoselective Synthesis of the Plant-growth-promoting Steroids Dolicholide and Dolichosterone

Stereoselective syntheses of dolicholide (3), (22R,23R)-2α,3α,22,23-tetrahydroxy-B-homo-7-oxa-5α-ergost-24(28)-en-6-one, and dolichosterone (4), (22R,23R)-2α,3α,22,23-tetrahydroxy-5α-ergost-24(28)-en-6-one, were achieved from the known (22E,24S)-2α,3α-diacetoxy-5α-stigmast-22-en-6-one (5) which is readily available from stigmasterol.The key step in the construction of the (22R,23R)-vicinal diol function in the steroidal side-chain was new and used the method of chelation control.