22S,23S-EPICASTASTERONE

Base Information

• Chemical Name: 22S,23S-EPICASTASTERONE
• CAS No.: 72050-69-2
• Molecular Formula: C₂₈H₄₈O₅
• Molecular Weight: 464.686
• Mol file: 72050-69-2.mol

Synonyms:22,23,24-Trisepicastasterone

Chemical Property of 22S,23S-EPICASTASTERONE

Chemical Property:

• PSA: 97.99000
• LogP: 3.80600

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Epicastasterone can be used as reactant/reagent in preparation for and plant growth-regulating activity of indolylacetoxy brassinosteroids.

Technology Process of 22S,23S-EPICASTASTERONE

There total 20 articles about 22S,23S-EPICASTASTERONE which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

→ (2R,3S,5S,17R)-17-((1S,4R)-2,3-Dihydroxy-1,4,5-trimethyl-hexyl)-2,3-dihydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-6-one (72050-69-2,72050-71-6,80736-41-0,80736-42-1,110416-32-5,113666-78-7,121398-05-8,121468-14-2,121468-15-3,121468-16-4,135559-13-6,147200-30-4,147200-31-5)

Guidance literature:

Dien 7, OsO4;

DOI:10.1021/jo00394a066

Reference yield:

→ (2R,3S,5S,10R,13S,17R)-17-((1S,2S,3S,4R)-2,3-Dihydroxy-1,4,5-trimethyl-hexyl)-2,3-dihydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-6-one (72050-69-2,72050-71-6,80736-41-0,80736-42-1,110416-32-5,113666-78-7,121398-05-8,121468-14-2,121468-15-3,121468-16-4,135559-13-6,147200-30-4,147200-31-5)

Guidance literature:

Dien 7, OsO4;

DOI:10.1021/jo00394a066

Reference yield:

Ergosterol (57-87-4) → (22S,23S,24R)-2α,3α,22,23-tetrahydroxy-5α-ergostan-6-one (72050-69-2,72050-71-6,80736-41-0,80736-42-1,110416-32-5,113666-78-7,121398-05-8,121468-14-2,121468-15-3,121468-16-4,135559-13-6,147200-30-4,147200-31-5)

Guidance literature:

Multi-step reaction with 6 steps

1: pyridine / Ambient temperature

2: water, potassium hydrocarbonate / acetone

3: CrO₃, pyridine

4: 94 percent / Li, liq. NH₃ / diethyl ether / 0.08 h / -70 - -60 °C

5: 72 percent / pyridine hydrobromide / dimethylformamide / Heating

6: OsO₄

With pyridine; chromium(VI) oxide; osmium(VIII) oxide; ammonia; water; Pyridine hydrobromide; lithium; potassium hydrogencarbonate; In diethyl ether; N,N-dimethyl-formamide; acetone;

upstream raw materials:

(22E,24R)-5α-ergosta-2,22-dien-6-one

Ergosterol

(22E,24R)-5α-ergosta-5,7,22-triene-3-p-toluenesulfonate

(22E,24R)-3α,5-cyclo-5α-ergosta-7,22-dien-6-one

Downstream raw materials:

(22R,23R,24R)-2α,3α,22,23-tetrahydro-B-homo-7-oxa-5α-ergostan-6-one

(22S,23S,24R)-2α,3α,22,23-tetrahydro-B-homo-7-oxa-5α-ergostan-6-one

Refernces

• 1、 Thompson,Mandava,Meudt,Lusby,Spaulding. "Synthesis and biological activity of brassinolide and its 22 beta, 23 beta-isomer: novel plant growth-promoting steroids.". . p. 567 - 580. Retrieved 2007/10/02.