82373-95-3

Usage

Uses

Used in Pharmaceutical Industry:
(22R,23R,24S)-2α,3α,22,23-tetrahydroxy-24-ethyl-B-homo-7-oxa-5α-cholestan-6-one is used as a pharmaceutical candidate for its potential therapeutic effects. Given its structural similarity to natural steroids and its tetrahydroxylated cholestan core, it may exhibit hormone-like activity or interact with biological receptors, making it a promising candidate for the development of new drugs targeting various diseases.
Used in Agricultural Industry:
As a derivative of Brassinolide, a plant hormone, (22R,23R,24S)-2α,3α,22,23-tetrahydroxy-24-ethyl-B-homo-7-oxa-5α-cholestan-6-one is used as a growth regulator in agriculture. It promotes cell elongation and division, which can lead to increased crop yields and improved plant health. Its application in this industry can contribute to more efficient and sustainable agricultural practices.
Used in Chemical Research:
(22R,23R,24S)-2α,3α,22,23-tetrahydroxy-24-ethyl-B-homo-7-oxa-5α-cholestan-6-one serves as a valuable compound for chemical research, particularly in the fields of organic chemistry and biochemistry. Its unique structure and stereochemistry make it an interesting subject for studying molecular interactions, synthesis pathways, and potential applications in various chemical processes.
Used in Drug Delivery Systems:
(22R,23R,24S)-2α,3α,22,23-tetrahydroxy-24-ethyl-B-homo-7-oxa-5α-cholestan-6-one's structural features and potential biological activity also make it a candidate for use in drug delivery systems. It could be employed as a carrier or component in the development of targeted drug delivery platforms, potentially improving the efficacy and bioavailability of therapeutic agents.

Upstream product

• 90524-95-1 (22R,23R,24S)-22,23-dihydroxy-24-ethyl-5α-cholestan-3,6-dione 
• 83509-42-6 28-homocastasterone 
• 74174-48-4 Acetic acid (1S,3aS,3bS,6aS,8S,9R,10aR,10bS,12aS)-8-acetoxy-1-((1S,2R,3R,4S)-2,3-diacetoxy-4-ethyl-1,5-dimethyl-hexyl)-10a,12a-dimethyl-6-oxo-hexadecahydro-5-oxa-benzo[3,4]cyclohepta[1,2-e]inden-9-yl ester 
• 74174-48-4 Acetic acid (1S,3aS,3bS,6aS,8S,9R,10aR,10bS,12aS)-8-acetoxy-1-((1S,2S,3S,4S)-2,3-diacetoxy-4-ethyl-1,5-dimethyl-hexyl)-10a,12a-dimethyl-6-oxo-hexadecahydro-5-oxa-benzo[3,4]cyclohepta[1,2-e]inden-9-yl ester 
• 83-48-7 Stigmasterol 
• 74174-45-1 (22E)-stigmasta-2,22-dien-6-one 
• 90524-97-3 (22R,23R,24S)-3β-hydroxy-22,23-isopropylidenedioxy-B-homo-7-oxa-5α-stigmastan-6-one 
• 90524-96-2 (22R,23R,24S)-3β,22,23-trihydroxy-B-homo-7-oxa-5α-stigmastan-6-one 
• 90540-47-9 (22R,23R,24S)-3β,22,23-triacetoxy-B-homo-7-oxa-5α-stigmastan-6-one 
• 90524-98-4 (22R,23R,24S)-22,23-isopropylidenedioxy-3β-methylsulphonyloxy-B-homo-7-oxa-5α-stigmastan-6-one 
• 90524-99-5 (22R,23R,24S)-22,23-isopropylidenedioxy-B-homo-7-oxa-5α-stigmast-2-en-6-one 
• 83509-43-7 (2R,3S,22R,23R,24S)-2,3,22,23-Tetraacetoxy-24-ethyl-B-homo-7-oxa-5α-cholestan-6-one 

Relevant academic research and scientific papers

Preparation method of 28-homobrassinolide

The invention relates to a preparation method of 28-homobrassinolide, and belongs to the technical field of organic synthesis. The preparation method comprises the following steps: preparing a corresponding asymmetric epoxide from (2,22)-diene-24S-ethyl-5alpha-cholest-6-one under the action of a chiral catalyst and an oxidizing agent, and then carrying out esterification, oxidation and hydrolysisreactions to obtain a product. The catalyst provided by the invention has the advantages of high selectivity, high efficiency, and low dosage, and the method has advantages of low cost, simple process, convenient operation, environmental protection and good industrial application value.

Preparation method of 28-homobrassinolide

The invention relates to a preparation method of 28-homobrassinolide, and belongs to the technical field of organic synthesis. The 28-homobrassinolide is obtained by taking (2,22)-dien-24S-ethyl-5[alpha]-cholest-6-one as a raw material through two steps comprising Sharpless asymmetric dihydroxylation and Baeyer-Villiger oxidation reaction under action of a chiral catalyst and an oxidizing agent. The preparation method is efficient and environmentally friendly, has few steps and simple process, is convenient to operate, and has a good industrial application value.

Preparation method for synthesizing 28-brassinolide through three-step method

The invention discloses a preparation method for synthesizing 28-brassinolide through a three-step method. According to the preparation method, the 28-brassinolide is prepared from the raw material (2,22)-diene-24S-ethyl-5alpha-cholest-6-ketone through oxidation, esterification and hydrolysis reaction. The preparation method has the advantages of green and environmental protection, no pollution, environmental friendliness, easily available raw material, wide source, low cost, simple method and suitability for industrialized production. By the preparation method, the problems in the prior art of high preparation cost and difficulty in industrialized production are solved.

Preparation method with four-step synthesis of 28-homobrassinolide

The invention discloses a preparation method with four-step synthesis of 28-homobrassinolide, which takes (2,22)-diene-24S-ethyl-5alpha-cholest-6-ketone as a raw material, and 28-homobrassinolide is obtained from epoxidation, esterification, Baeyer-Villiger oxidation and hydrolysis reaction, the preparation method provided by the invention has the advantages of green environmental protection, no pollution, environment friendliness, easily available raw materials, wide source, low cost, simple method and suitability for industrial production, and the preparation method solves the problems of high preparation cost and difficulty in industrial production in the prior art.

Brassinosteroids and analogs as neuroprotectors: Synthesis and structure-activity relationships

We have demonstrated previously that the brassinosteroid (BR) 24-epibrassinolide exerts neuroprotective effects deriving from its antioxidative properties. In this study, we synthesized 2 natural BRs and 5 synthetic analogs and analyzed their neuroprotect

SYNTHESIS AND BIOLOGICAL ACTIVITY OF 28-HOMOBRASSINOLIDE AND ANALOGUES

28-Homobrassinolide has been synthesized from stigmasterol in an overall yield of 21percent.The biological activity of 28-homobrassinolide, brassinolide, 24-epibrassinolide, 22S,23S,24-epibrassinolide, and 22S,23S,28-homobrassinolide have been compared in the soybean epicotyl elongation assay.All the steroids except 22S,23S,28-homobrassinolide exhibited a similar biological activity, but the latter compound was substantially less active.There appears to be a correlation between biological activity and overall dimensions of the steroidal side chain.

STEREOSELECTIVE SYNTHESIS OF THE BRASSINOLIDE SIDE CHAIN: NOVEL SYNTHESIS OF BRASSINOLIDE AND RELATED COMPOUNDS

A stereoselective synthesis of the brassinolide side chain involves the lactonization of Z-10 under acidic condition to give an α,β-unsaturated-δ-lactone 11 with the inversion of the configuration at C-22 of the epoxy steroid in quantitative yield.The 22R,23R,24R-γ-hydroxy-δ-lactone 14 was used as key intermediate for the syntheses of brassinolide (1), homobrassinolide (2), and typhasterol (4) as well as the side chain of the dolicholide (3).

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 and Activity of Plant Growth-promoting Steroids, (22R,23R,24S)-28-Homobrassinosteroids, with Modifications in Rings A and B

In order to investigate the structure-activity relationship of brassinosteroids, fourteen (22R,23R,24S)-28-homobrassinosteroids with modifications in rings A and B were synthesized from (22E,24S)-3β-hydroxy-5α-stigmast-22-en-6-one (3a).The (22E,23R)-vicinal diol was introduced by epoxidation of the trans-C-22(23) double bond, followed by trans ring-opening of the resulting epoxides by HBr-AcOH, and then an inversion reaction at the carbon bearing bromine by acetoxy anion to give (22R,23R,24S)-3β,22,23-triacetoxy-5α-stigmastan-6-one (8a).Baeyer-Villiger oxidaton of (8a) gave the two regioisomeric 6-oxa- and 7-oxa-lactones (15a) and (16a).Introduction of a 3α-hydroxy group and C-2(3) or C-3(4) double bond was achieved by treatment of the 3β-methanesulphonate (10b), (17b), or (25b) with lithium carbonate in refluxing dimethylformamide.Further elaboration of ring A gave 28-homobrassinosteroids, 2-deoxybrassinosteroids, 2-deoxy-4α-hydroxybrassinosteroids, and their regioisomeric 6-oxolactone compounds.Bioassay using the rice-lamina inclination test indicated that the 3α,4α-diol analogue (23) has almost the same activity as the 2α,3α-diol (1b), and the 2-deoxysteroids (13) and (21) were also highly active, showing one-tenth the activity of the 28-homobrassinolide (1b).The following structural features of brassinosteroids are important for the high activity: (i) the (22R,23R)-vicinal diol moiety; (ii) the (24S)-methyl- or ethyl group; (iii) the 7-oxalactone or 6-oxo functionality in the B-ring; (iv) a 3α-hydroxy group, 2α,3α-vicinal diol, or 3α,4α-vicinal diol; and (v) an A,B-trans-fused ring junction.

Synthesis of Analogues of Brassinolide and Castasterone

Syntheses of 2α,3α,22R,23R-tetrahydroxy-24S-ethyl-B-homo-7-oxa-5α-cholestan-6-one (5) and 2α,3α-dihydroxy-24S-ethyl-B-homo-7-oxa-5α-cholestan-6-one (7) are described starting from stigmasterol and β-sitosterol respectively.