7,8-Dihydromorphine-6-glucuronide

Base Information

• Chemical Name: 7,8-Dihydromorphine-6-glucuronide
• CAS No.: 70001-26-2
• Molecular Weight: 463.48
• DSSTox Substance ID: DTXSID801018775
• Nikkaji Number: J1.274.871J
• Mol file: 70001-26-2.mol

Synonyms:70001-26-2;DTXSID801018775;7,8-Dihydromorphine-6-glucuronide

Chemical Property of 7,8-Dihydromorphine-6-glucuronide

Chemical Property:

• Boiling Point: 727.0±60.0 °C(Predicted)
• PKA: 2.80±0.70(Predicted)
• Density: 1.61±0.1 g/cm3(Predicted)
• Storage Temp.: -20°C
• XLogP3: -1.8
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 3
• Exact Mass: 463.18423150
• Heavy Atom Count: 33
• Complexity: 798

Purity/Quality:

Dihydromorphine-3-D-glucuronide solution 1.0 mg/mL in methanol: water (1:1), certified reference material ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CN1CCC23C4C1CC5=C2C(=C(C=C5)O)OC3C(CC4)OC6C(C(C(C(O6)C(=O)O)O)O)O
• Isomeric SMILES: CN1CC[C@]23[C@@H]4[C@H]1CC5=C2C(=C(C=C5)O)O[C@H]3[C@H](CC4)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)C(=O)O)O)O)O
• Uses: Dihydromorphine 6-O-β-D-Glucuronide is a metabolite of Hydromorphone (H714650).

Technology Process of 7,8-Dihydromorphine-6-glucuronide

There total 9 articles about 7,8-Dihydromorphine-6-glucuronide 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: 85.0%

C32H39NO14 (330823-63-7) → Dihydromorphine 6-β-D-glucuronide (70001-26-2)

Guidance literature:

With sodium hydroxide; In methanol; at 20 ℃;

DOI:10.1016/S0040-4020(00)01080-2

Reference yield:

dihydromorphine (509-60-4,13004-73-4,26626-12-0) → Dihydromorphine 6-β-D-glucuronide (70001-26-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 100 percent / aq. NaHCO₃ / methanol; CH₂Cl₂ / 1 h / 0 - 20 °C

2: 75 percent / 3 Angstroem molecular sieves; ZnBr₂ / CHCl₃ / Heating

3: 85 percent / aq. NaOH / methanol / 20 °C

With sodium hydroxide; 3 A molecular sieve; sodium hydrogencarbonate; zinc dibromide; In methanol; dichloromethane; chloroform;

DOI:10.1016/S0040-4020(00)01080-2

Reference yield:

(3R,4S,5S,6S)-2-bromo-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (57820-69-6) → Dihydromorphine 6-β-D-glucuronide (70001-26-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 75 percent / 3 Angstroem molecular sieves; ZnBr₂ / CHCl₃ / Heating

2: 85 percent / aq. NaOH / methanol / 20 °C

With sodium hydroxide; 3 A molecular sieve; zinc dibromide; In methanol; chloroform;

DOI:10.1016/S0040-4020(00)01080-2

upstream raw materials:

C₄₃H₅₃NO₁₃

C₃₂H₃₉NO₁₄

(3R,4S,5S,6S)-2-bromo-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

3-O-methoxycarbonyl dihydromorphine

Refernces

• 1、 Rukhman,Yudovich,Nisnevich,Gutman. "6-O-Glycosylation of morphine derivatives using thioglycosides as glycosyl donors". . p. 1241 - 1246. Retrieved 2007/10/03.