(11beta,16alpha)-9-Fluoro-11,17-dihydroxy-21-iodo-16-methylpregna-1,4-diene-3,20-dione

Base Information

• Chemical Name: (11beta,16alpha)-9-Fluoro-11,17-dihydroxy-21-iodo-16-methylpregna-1,4-diene-3,20-dione
• CAS No.: 2029-18-7
• Molecular Formula: C22H28 F I O4
• Molecular Weight: 502.36
• DSSTox Substance ID: DTXSID001135597
• Mol file: 2029-18-7.mol

Synonyms:DTXSID001135597;(11beta,16alpha)-9-Fluoro-11,17-dihydroxy-21-iodo-16-methylpregna-1,4-diene-3,20-dione

Chemical Property of (11beta,16alpha)-9-Fluoro-11,17-dihydroxy-21-iodo-16-methylpregna-1,4-diene-3,20-dione

Chemical Property:

• PSA: 74.60000
• LogP: 3.33840
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 502.10164
• Heavy Atom Count: 28
• Complexity: 808

Purity/Quality:

Dexamethasone21-Iodide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CC2C3CCC4=CC(=O)C=CC4(C3(C(CC2(C1(C(=O)CI)O)C)O)F)C
• Isomeric SMILES: C[C@@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@@]4([C@]3([C@H](C[C@@]2([C@]1(C(=O)CI)O)C)O)F)C
• Uses: Dexamethasone 21-Iodide is a derivative of Dexamethasone (D298800), a glucocorticoid used as an anti-inflammatory agent.

Technology Process of (11beta,16alpha)-9-Fluoro-11,17-dihydroxy-21-iodo-16-methylpregna-1,4-diene-3,20-dione

There total 2 articles about (11beta,16alpha)-9-Fluoro-11,17-dihydroxy-21-iodo-16-methylpregna-1,4-diene-3,20-dione 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: 74.3%

Dexamethasone 21-mesylate (2265-22-7) → 9-fluoro-11β,17-dihydroxy-21-iodo-16α-methylpregn-4-ene-3,20-dione (2029-18-7)

Guidance literature:

With sodium iodide; In acetone; for 0.666667h; Heating;

Reference yield:

dexamethasone (50-02-2) → 9-fluoro-11β,17-dihydroxy-21-iodo-16α-methylpregn-4-ene-3,20-dione (2029-18-7)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / 1.5 h / 0 °C

2: NaI / acetone / 2 h / Heating

With pyridine; sodium iodide; In acetone;

DOI:10.1016/0223-5234(91)90137-C

Reference yield: 25.0%

N,N'-bis-benzyloxycarbonylcystine (6968-11-2,102203-30-5,102339-44-6) + 9-fluoro-11β,17-dihydroxy-21-iodo-16α-methylpregn-4-ene-3,20-dione (2029-18-7) → C66H78F2N2O16S2 (140209-98-9)

Guidance literature:

With triethylamine; In N,N-dimethyl-formamide; at 40 ℃; for 2h;

DOI:10.1016/0223-5234(91)90137-C

upstream raw materials:

Dexamethasone 21-mesylate

dexamethasone

Downstream raw materials:

C₆₆H₇₈F₂N₂O₁₆S₂

Refernces

• 1、 Rapi, Gianfranco,Ginanneschi, Mauro,Chelli, Mario. "A Facile Synthesis of 21-(1-Imidazolyl) Steroids". . p. 101 - 109. Retrieved 2007/10/02.