Morphine 3,6-diglucuronide

Base Information

• Chemical Name: Morphine 3,6-diglucuronide
• CAS No.: 64947-41-7
• Molecular Formula: C₂₉H₃₅NO₁₅
• Molecular Weight: 637.595
• European Community (EC) Number: 635-728-3
• DSSTox Substance ID: DTXSID901018778
• Nikkaji Number: J492.497E
• Wikidata: Q76422130
• Mol file: 64947-41-7.mol

Synonyms:64947-41-7;Morphine 3,6-diglucuronide;morphine-3,6-diglucuronide;SCHEMBL3017103;DTXSID901018778

Chemical Property of Morphine 3,6-diglucuronide

Chemical Property:

• Melting Point: 240-245 °C (dec.)
• Boiling Point: 951.7±65.0 °C(Predicted)
• PKA: 2.77±0.70(Predicted)
• PSA: 245.37000
• Density: 1.76±0.1 g/cm3(Predicted)
• LogP: -3.38210
• Storage Temp.: 2-8°C
• XLogP3: -4.4
• Hydrogen Bond Donor Count: 8
• Hydrogen Bond Acceptor Count: 16
• Rotatable Bond Count: 6
• Exact Mass: 637.20066941
• Heavy Atom Count: 45
• Complexity: 1200

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 20/21/22-43
• Safety Statements: 36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1CCC23C4C1CC5=C2C(=C(C=C5)OC6C(C(C(C(O6)C(=O)O)O)O)O)OC3C(C=C4)OC7C(C(C(C(O7)C(=O)O)O)O)O
• Isomeric SMILES: CN1CC[C@]23[C@@H]4[C@H]1CC5=C2C(=C(C=C5)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)C(=O)O)O)O)O)O[C@H]3[C@H](C=C4)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)C(=O)O)O)O)O

Technology Process of Morphine 3,6-diglucuronide

There total 3 articles about Morphine 3,6-diglucuronide 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: 89.0%

morphine-3,6-di(methyl 2,3,4-tri-O-isobutyryl-β-D-glucopyranuronate) (150607-98-0) → morphine-3,6-di-β-D-glucuronide (64947-41-7)

Guidance literature:

With sodium hydroxide; acetic acid; In methanol;

DOI:10.1016/S0040-4020(00)00664-5

Reference yield:

(2S,3S,4S,5R,6R)-2-(methoxycarbonyl)-6-(2,2,2-trichloro-1-iminoethoxy)tetrahydro-2H-pyran-3,4,5-triyl tris(2-methylpropanoate) (150607-96-8) → morphine-3,6-di-β-D-glucuronide (64947-41-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 60 percent / BF₃*Et₂O; 4A molecular sieves / CH₂Cl₂ / 48 h / 20 °C

2: 89 percent / aq. NaOH; glacial acetic acid / methanol

With sodium hydroxide; 4 A molecular sieve; boron trifluoride diethyl etherate; acetic acid; In methanol; dichloromethane; 1: Substitution / 2: Hydrolysis;

DOI:10.1016/S0040-4020(00)00664-5

Reference yield:

methyl 2,3,4-tri-O-isobutyryl-D-glucopyranuronate → morphine-3,6-di-β-D-glucuronide (64947-41-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 85 percent / Na₂CO₃ / CH₂Cl₂

2: 60 percent / BF₃*Et₂O; 4A molecular sieves / CH₂Cl₂ / 48 h / 20 °C

3: 89 percent / aq. NaOH; glacial acetic acid / methanol

With sodium hydroxide; 4 A molecular sieve; boron trifluoride diethyl etherate; sodium carbonate; acetic acid; In methanol; dichloromethane; 1: Addition / 2: Substitution / 3: Hydrolysis;

DOI:10.1016/S0040-4020(00)00664-5

upstream raw materials:

morphine-3,6-di(methyl 2,3,4-tri-O-isobutyryl-β-D-glucopyranuronate)

(2S,3S,4S,5R,6R)-2-(methoxycarbonyl)-6-(2,2,2-trichloro-1-iminoethoxy)tetrahydro-2H-pyran-3,4,5-triyl tris(2-methylpropanoate)

Refernces