22425-77-0

Upstream product

• 22425-82-7 methyl maslinate 
• 108-24-7 acetic anhydride 
• 557765-95-4 C₃₁H₄₈O₆S 
• 292859-56-4 methyl 2α-tosyloxy-3β-hydroxy-12-oleanen-28-oate 
• 127-08-2 potassium acetate 
• 292859-65-5 methyl 2β,3β-epoxy-12-oleanen-28-oate 

Downstream Products

• 35482-95-2 methyl 2α-acetoxy-3-oxo-12-oleanen-28-oate 

Relevant academic research and scientific papers

Remote hydroxylation of methyl groups by regioselective cyclopalladation. Partial synthesis of hyptatic acid-A

(Chemical Equation Presented) Hyptatic acid-A (32), a 2α,3β,24- trihydroxyolean-12-en-28-oic acid, previously isolated from Hyptis capitata, was obtained from maslinic acid (2). The regioselective cyclopalladation of the axial methyl group on C-4 of maslinic acid afforded the C-24 hydroxymethylene group due to the presence of a C-2-OR substituent. Nevertheless, hederagenin (7) (23-hydroxy derivative) was formed when this oxygenated group was not present.

Epoxides, cyclic sulfites, and sulfate from natural pentacyclic triterpenoids: Theoretical calculations and chemical transformations

Several triterpenic derivatives, with the A-ring functionalized, were semisynthesized from oleanolic and maslinic acids. The reactivities of sulfites, sulfate, and epoxides in these triterpene compounds were investigated under different reaction conditions. Moreover, contracted A-ring triterpenes (five-membered rings) were obtained, by different treatments of the sulfate 7. From the epoxide 8, deoxygenated and halohydrin derivatives were semisynthesized with several nucleophiles. Ozonolysis and Beckmann reactions were used to yield 4-aza compounds, from five-membered ring olanediene triterpenes. The X-ray structure of sulfate 7 is given and compared with density functional theory geometries. Theoretical 13C and 1H chemical shifts (gauge-invariant atomic orbital method at the B3LYP/6-31G*//B3LYP/6-31G* level) and 3JH,H coupling constants were calculated for compounds 5-9 and 34-36, identifying the (R)- or (S)-sulfur and α- or β-epoxide configurations together with 4-aza or 3-aza structures.

Semi-synthesis of triterpene A-ring derivatives from oleanolic and maslinic acids. Part II. Theoretical and experimental 13C chemical shifts

Maslinic acid was obtained from olive-pressing residues, an several derivatives were formed. Rearrangements of 2-tosyloxy-derivatives of methyl maslinate made out by acetolysis. The main product of these rearrangements contained a cyclopentanic A-ring as