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Usage

Uses

Used in Biological Studies:
Typhasterol is used in biological studies for understanding the role of plant steroid hormones produced under Ni stress in the regulation of metal uptake and oxidative stress in Brassica juncea L. This helps in exploring the potential applications of Typhasterol in improving plant growth and stress tolerance.
Used in Agriculture:
Typhasterol can be used in agriculture as a plant growth regulator to enhance the growth and productivity of crops. Its role in regulating metal uptake and oxidative stress can help in developing stress-tolerant crop varieties and improving crop yields under adverse environmental conditions.
Used in Pharmaceutical Industry:
Although not explicitly mentioned in the provided materials, due to its classification as a brassinosteroid, Typhasterol may have potential applications in the pharmaceutical industry for the development of drugs targeting various physiological processes in humans. Further research would be required to explore its potential uses and efficacy in this industry.

Upstream product

• 124853-28-7 3-dehydroteasterone 
• 83066-62-0 Acetic acid (3S,8S,9S,10R,13S,14S,17R)-17-{(S)-1-[(4R,5R)-5-((S)-1-formyl-2-methyl-propyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-ethyl}-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester 
• 76976-84-6 (22R,23R,24R)-23,24-epoxy-3β-tetrahydropyranyloxycholest-5-en-22-ol acetate 
• 90095-31-1 C₃₄H₅₆O₇S 
• 83066-70-0 (22R,23R,24S)-22,23-isopropylidenedioxy-6-oxo-5α-ergostan-3β-yl methanesulphonate 
• 115350-48-6 Acetic acid (3R,5R,6S,8S,9S,10R,13S,14S,17R)-3-acetoxy-17-[(1S,2R)-2-hydroxy-1-methyl-2-((2R,3S)-3-methyl-5-oxo-tetrahydro-furan-2-yl)-ethyl]-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-6-yl ester 
• 115350-55-5 (22R,23R,24S)-3α,6α,22-triacetoxy-23-hydroxy-27-nor-5β-ergostan-26-oic acid lactone 
• 134224-84-3 (22R,23R)-3α,6α,22-triacetoxy-23-hydroxy-27-nor-5β-ergost-24-en-26-oic acid lactone 
• 115350-59-9 (3R,5R,6S,8S,9S,10R,13S,14S,17R)-17-{(S)-1-[(4R,5R)-5-((S)-2-[1,3]Dithian-2-yl-1-methyl-propyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-ethyl}-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthrene-3,6-diol 
• 124853-27-6 (22R,24S)-3α,6α-diacetoxy-24-carboxyethyl-5β-cholesten-22(29)-lact-23-one 
• 115368-99-5 Acetic acid (3R,5R,6S,8S,9S,10R,13S,14S,17R)-3-acetoxy-17-[(1S,2R)-2-hydroxy-1-methyl-2-((R)-3-methyl-5-oxo-2,5-dihydro-furan-2-yl)-ethyl]-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-6-yl ester 
• 115350-56-6 Propionic acid (3R,5R,6S,8S,9S,10R,13S,14S,17R)-17-[(1S,2R)-2-acetoxy-2-((2R,3S)-3,4-dimethyl-5-oxo-tetrahydro-furan-2-yl)-1-methyl-ethyl]-10,13-dimethyl-3-propionyloxy-hexadecahydro-cyclopenta[a]phenanthren-6-yl ester 
• 115350-52-2 Toluene-4-sulfonic acid (S)-3-{(4R,5R)-5-[(S)-1-((3R,5R,6S,8S,9S,10R,13S,14S,17R)-3,6-dihydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-methyl-butyl ester 
• 115350-49-7 Propionic acid (3R,5R,6S,8S,9S,10R,13S,14S,17R)-17-[(1S,2R)-2-((2R,3S)-3,4-dimethyl-5-oxo-tetrahydro-furan-2-yl)-2-hydroxy-1-methyl-ethyl]-10,13-dimethyl-3-propionyloxy-hexadecahydro-cyclopenta[a]phenanthren-6-yl ester 

Relevant academic research and scientific papers

3-Oxoteasterone and the Epimerization of Teasterone: Identification in Lily Anthers and Distylium racemosum Leaves and Its Biotransformation into Typhasterol

3-Oxo TE has been assumed to be involved as a biosynthetic intermediate in the epimerization of the C-3 hydroxyl group of teasterone to typhasterol.We have isolated and identified it in lily anthers by using normal-phase HPLC.Mass spectral analysis, chemical synthesis and identification of the biotransformation product by lily cell cultures confirmed it to be 3-oxo TE.Reduction of this compound stereoselectively transformed it into typhasterol in cell cultures.It is suggested that 3-oxo TE is distributed widely in the plant kingdom as a biosynthetic intermediate from TE to TY.

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.

Facile Syntheses of Brassinosteroids: Brassinolide, Castasterone, Teasterone and Typhasterol

(22R,23R,24S)-3α,5-Cyclo-22,23-diacetoxy-5α-ergostan-6-one (2b) is a new key intermediate of some naturally occuring brassinosteroids such as brassinolide (1a), castasterone (1b), teasterone (1c) and typhasterol (1d).The cycloketone 2b was prepared in 10 steps via (22R,23R,24S)-6β-benzyloxy-3α,5-cyclo-22,23-dihydroxy-5α-ergostane (5) from stigmasterol. 2b was treated with a catalytic amount of p-toluenesulfonic acid and sodium bromide to give an enone (7b), which was oxidized with osmium tetroxide and derived to give a 2α,3α-acetonide (8b). 8b was easily separated from its isomer by the use of silica gel column chromatography. 8b was oxidized with trifluoroperacetic acid and deacetylated to give 1a. 8b was deacetylated and deacetonized to give 1b. 2b was treated with dilute sulfuric acid in acetic acid to give a 3β-acetate (10). 10 was treated with sodium hydroxide to give 1c. 2b was treated with hydrobromic acid to give a 3β-bromide (12), which was treated with silver acetate to give a 3α-acetate (13). 13 was treated with sodium hydroxide to give 1d.

STUDY ON THE SYNTHESIS OF BRASSINOLIDE AND RELATED COMPOUNDS III STEREOSELECTIVE SYNTHESIS OF TYPHASTEROL FROM HYODEOXYCHOLIC ACID

Typhasterol 2 was synthesized stereoselectively from hyodeoxycholic acid 3.The aldehyde 5 derived from 3 was reacted with the anion of 3-methylbutenolide under kinetic condition to afford (22R,23R)-7 as the major product.Hydrogenation of 7 and its 22-acet

Synthesis of Teasterone and Typhasterol, Brassinolide-related Steroids with Plant-growth-promoting Activity

Brassinolide-related natural steroids, teasterone (4), (22R,23R,24S)-3β,22,23-trihydroxy-5α-ergostan-6-one, and typhasterol (3), 3α-isomer of (4), have been synthesized from crinosterol (5).The cyclopropyl ketone (6), obtained by solvolysis of crinosterol methanesulphonate followed by Jones oxidation, was transformed by treatment with acid and acetylation into (22E,24S)-6-oxo-5α-ergost-22-en-3β-yl acetate (7), which was epoxidized.Epoxide-ring opening of the separated (22R,23R)-epoxide (9) with 30 percent HBr-AcOH, followed by inversion reaction at the carbon bearing bromine, and acetylation, provided the (22R,23R,24S)-triacetate (10), which was saponified to yield teasterone (4).The sulphonate (11), derived from teasterone (4), was submitted to an improved inversion reaction with caesium acetate.Deprotection of the resulting 3α-acetate (12) provided typhasterol (3).

Stereoselective Synthesis of Plant Growth-promoting Steroids, Brassinolide, Castasterone, Typhasterol, and Their 28-Nor Analogues

Plant growth-promoting steroids, brassinolide (1a), (22R,23R,24S)-2α,3α,22,23-tetrahydroxy-B-homo-7-oxa-5α-ergostan-6-one, castasterone (2a), (22R,23R,24S)-2α,3α,22,23-tetrahydroxy-5α-ergostan-6-one, 28-norbrassinolide (1b), (22R,23R)-2α,3α,22,23-tetrahydroxy-B-homo-7-oxa-5α-cholestan-6-one, brassinone (2b), (22R,23R)-2α,3α,22,23-tetrahydroxy-5α-cholestan-6-one, and typhasterol (2c), (22R,23R,24S)-3α,22,23-trihydroxy-5α-ergostan-6-one, have been stereoselectively synthesized.These steroids show very strong biological activities in three different kinds of bioassays.