6-(5'-Nitro-2'-pyridyldithio)deoxydihydromorphine

Base Information

• Chemical Name: 6-(5'-Nitro-2'-pyridyldithio)deoxydihydromorphine
• CAS No.: 130178-43-7
• Molecular Formula: C₂₂H₂₃N₃O₄S₂
• Molecular Weight: 457.574
• DSSTox Substance ID: DTXSID90926624
• Mol file: 130178-43-7.mol

Synonyms:6-(5'-nitro-2'-pyridyldithio)deoxydihydromorphine;NPDM

Chemical Property of 6-(5'-Nitro-2'-pyridyldithio)deoxydihydromorphine

Chemical Property:

• Boiling Point: 649°Cat760mmHg
• Flash Point: 346.3°C
• PSA: 142.01000
• Density: 1.53g/cm³
• LogP: 4.63460
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 3
• Exact Mass: 457.11299857
• Heavy Atom Count: 31
• Complexity: 725

Purity/Quality:

85.0-99.8% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1CCC23C4C1CC5=C2C(=C(C=C5)O)OC3C(CC4)SSC6=NC=C(C=C6)[N+](=O)[O-]
• Isomeric SMILES: CN1CCC23[C@@H]4[C@H]1CC5=C2C(=C(C=C5)O)O[C@@H]3[C@@H](CC4)SSC6=NC=C(C=C6)[N+](=O)[O-]

Technology Process of 6-(5'-Nitro-2'-pyridyldithio)deoxydihydromorphine

There total 5 articles about 6-(5'-Nitro-2'-pyridyldithio)deoxydihydromorphine 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: 84.0%

5-Nitro-2-pyridinesulfenyl chloride (130156-01-3) + 6-β-sulfhydryldihydromorphine (22223-00-3) → 6-β-<5-nitro-2-pyridinesulfenyl>thio-dihydromorphine (130178-43-7)

Guidance literature:

In dichloromethane; at 0 ℃;

DOI:10.1248/cpb.38.1438

Reference yield:

3-acetoxy-6-β-acetylthiodihydromorphine (22222-98-6) → 6-β-<5-nitro-2-pyridinesulfenyl>thio-dihydromorphine (130178-43-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 531 mg / NaBH₄ / ethanol / 1 h / Ambient temperature

2: 397 mg / K₂CO₃ / CH₂Cl₂ / 0.17 h / Ambient temperature

With sodium tetrahydroborate; potassium carbonate; In ethanol; dichloromethane;

DOI:10.1016/S0968-0896(96)00219-2

Reference yield:

3-O-acetyldihydromorphine (58752-60-6) → 6-β-<5-nitro-2-pyridinesulfenyl>thio-dihydromorphine (130178-43-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 76 percent / diisopropylazodicarboxylate, Ph₃P / tetrahydrofuran

2: 531 mg / NaBH₄ / ethanol / 1 h / Ambient temperature

3: 397 mg / K₂CO₃ / CH₂Cl₂ / 0.17 h / Ambient temperature

With sodium tetrahydroborate; di-isopropyl azodicarboxylate; potassium carbonate; triphenylphosphine; In tetrahydrofuran; ethanol; dichloromethane;

DOI:10.1016/S0968-0896(96)00219-2

upstream raw materials:

5-Nitro-2-pyridinesulfenyl chloride

6-β-sulfhydryldihydromorphine

3-acetoxy-6-β-acetylthiodihydromorphine

3-O-acetyldihydromorphine