4736-92-9

Upstream product

• 20817-72-5 (22E)-stigmasta-4,22-dien-3-one 
• 71-41-0 pentan-1-ol 
• 83-48-7 Stigmasterol 
• 71-23-8 propan-1-ol 
• 4736-95-2 5α-stigmast-22-en-3-one 
• 5405-37-8 24-ethyl-5α-cholest-22-en-3β-yl acetate 

Downstream Products

• 5405-37-8 5β-stigmasten-(22t)-yl-(3α)-acetate 
• 53106-51-7 benzoic acid-(5β-stigmasten-(22t)-yl-(3α)-ester) 
• 83-45-4 Stigmastanol 
• 5405-37-8 24-ethyl-5α-cholest-22-en-3β-yl acetate 
• 108814-74-0 benzoic acid-(5α-stigmasten-(22t)-yl-(3β)-ester) 
• 110556-84-8 (2S,3S,4R,5S)-3-Ethyl-2-methyl-5-phenylselanyl-6-((1R,3aS,3bR,5aS,6aS,9aR,10aS,10bS,12aS)-8,8,10a,12a-tetramethyl-hexadecahydro-7,9-dioxa-dicyclopenta[a,h]phenanthren-1-yl)-heptan-4-ol 
• 110612-23-2 (2S,3R,4S,5S)-5-Ethyl-6-methyl-4-phenylselanyl-2-((1R,3aS,3bR,5aS,6aS,9aR,10aS,10bS,12aS)-8,8,10a,12a-tetramethyl-hexadecahydro-7,9-dioxa-dicyclopenta[a,h]phenanthren-1-yl)-heptan-3-ol 

Relevant academic research and scientific papers

TERPENOIDS AND STEROLS FROM THE WOOD OF ABIES PINSAPO

From the neutral fraction of the hexane extract of the wood of Abies pinsapo 11 sesquiterpenoids, seven diterpenoids, three triterpenoids and two sterols have been identified.Three of them are new natural products: 3β-hydroxy-13-epimanool, (23R,25R)-3α-methoxy-9,19-cyclo-9β-lanostan-26,23-olide and (22S)-5α-ergostane-3α,22-diol.Their structure were established by spectroscopic methods and chemical correlations. Key words: Abies pinsapo; Pinaceae; wood; labdane diterpenoids; cyclolanostanolides; sterols.

Synthesis of 6-Deoxohomodolichosterone, a New Plant-growth-promoting Steroid

6-Deoxohomodolichosterone (1), a new member of the brassinosteroid family, was synthesized in twelve steps from stigmasterol (4).Birch reduction of the dienone (5) gave directly 5α-stigmast-22-en-3β-ol (6), the mesylate of which was treated with lithium bromide in refluxing dimethylformamide.Selective oxidation of the 2-ene function of the resulting 2,22-diene (7), followed by acetonide formation, provided the acetonide 22-alkene (8).Epoxide-ring opening of the (22R,23R)-epoxide (9), derived from (8), with phenylselenolate anion, treatment with 30percent hydrogen peroxide, and epoxidation with peracid afforded the 22-hydroxy-23,24-epoxide (15).Ready cleavage of the epoxide ring of compound (15) with aluminium isopropoxide and deprotection yielded 6-deoxohomodolichosterone (1).