Rubrosterone

Base Information

• Chemical Name: Rubrosterone
• CAS No.: 19466-41-2
• Molecular Formula: C₁₉H₂₆O₅
• Molecular Weight: 334.412
• UNII: ND477TPA7H
• ChEMBL ID: CHEMBL2087163
• Metabolomics Workbench ID: 155692
• Nikkaji Number: J14.207G
• Wikidata: Q7376194
• Wikipedia: Rubrosterone
• Mol file: 19466-41-2.mol

Synonyms:rubrosterone

Chemical Property of Rubrosterone

Chemical Property:

• Vapor Pressure: 6.06E-14mmHg at 25°C
• Boiling Point: 540.7°Cat760mmHg
• Flash Point: 294.8°C
• PSA: 94.83000
• Density: 1.34g/cm³
• LogP: 1.14390
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 0
• Exact Mass: 334.17802393
• Heavy Atom Count: 24
• Complexity: 654

Purity/Quality:

98%,99%, ^*data from raw suppliers

Rubrosteron ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC3C(=CC(=O)C4C3(CC(C(C4)O)O)C)C1(CCC2=O)O
• Isomeric SMILES: C[C@]12CC[C@H]3C(=CC(=O)[C@H]4[C@@]3(C[C@@H]([C@@H](C4)O)O)C)[C@@]1(CCC2=O)O
• Uses: Rubrosterone, possessing various remarkable bioactivities, is an insect-molting C19-steroid.

Technology Process of Rubrosterone

There total 11 articles about Rubrosterone 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:

rubrosterone 2,3-acetonide (19896-54-9) → rubrosterone (55191-58-7,144405-76-5,19466-41-2)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane;

Reference yield:

Acetic acid (2S,3R,5S,9R,10R,13S,14R)-3-acetoxy-14-hydroxy-10,13-dimethyl-6,17-dioxo-2,3,4,5,6,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-2-yl ester (27957-69-3) → rubrosterone (55191-58-7,144405-76-5,19466-41-2)

Guidance literature:

With sodium hydrogencarbonate; In methanol; Heating;

Reference yield:

5α-Androsta-2,7-dien-6α,17β-diol → rubrosterone (55191-58-7,144405-76-5,19466-41-2)

Guidance literature:

Multi-step reaction with 5 steps

1: CrO₃*2Py / CH₂Cl₂ / Ambient temperature

2: I₂ / acetic acid

3: (acetylation)

4: SeO₂ / 2-methyl-propan-2-ol; pyridine / Heating

5: aq. NaHCO₃ / methanol / Heating

With selenium(IV) oxide; iodine; dipyridine chromium trioxide; sodium hydrogencarbonate; In pyridine; methanol; dichloromethane; acetic acid; tert-butyl alcohol;

upstream raw materials:

Acetic acid (2S,3R,5S,9R,10R,13S,14R)-3-acetoxy-14-hydroxy-10,13-dimethyl-6,17-dioxo-2,3,4,5,6,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-2-yl ester

rubrosterone 2,3-acetonide

5α-Androsta-2,7-dien-6,17-dion

Acetic acid (2S,3R,5S,9R,10R,13S,14S)-3-hydroxy-10,13-dimethyl-6,17-dioxo-2,3,4,5,6,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-2-yl ester

Downstream raw materials:

rubrosterone 2,3-acetonide