(s)-Propranolol glucuronide

Base Information

• Chemical Name: (s)-Propranolol glucuronide
• CAS No.: 58657-78-6
• Molecular Formula: C₂₂H₂₉NO₈
• Molecular Weight: 435.474
• UNII: L5J3CW7Z7X
• DSSTox Substance ID: DTXSID901310269
• Nikkaji Number: J602.782B
• Mol file: 58657-78-6.mol

Synonyms:(s)-propranolol glucuronide;(-)-Propranolol glucuronide;L5J3CW7Z7X;Propranolol glucuronide, (-)-;(2S,3S,4S,5R,6R)-3,4,5-Trihydroxy-6-((2S)-1-naphthalen-1-yloxy-3-(propan-2-ylamino)propan-2-yl)oxyoxane-2-carboxylic acid;UNII-L5J3CW7Z7X;DTXSID901310269;(1S)-1-(((1-METHYLETHYL)AMINO)METHYL)-2-(1-NAPHTHALENYLOXY)ETHYL .BETA.-D-GLUCOPYRANOSIDURONIC ACID;(1S)-1-(((1-Methylethyl)amino)methyl)-2-(1-naphthalenyloxy)ethyl beta-D-glucopyranosiduronic acid;.BETA.-D-GLUCOPYRANOSIDURONIC ACID, (1S)-1-(((1-METHYLETHYL)AMINO)METHYL)-2-(1-NAPHTHALENYLOXY)ETHYL;beta-D-Glucopyranosiduronic acid, (1S)-1-(((1-methylethyl)amino)methyl)-2-(1-naphthalenyloxy)ethyl

Chemical Property of (s)-Propranolol glucuronide

Chemical Property:

• XLogP3: -0.7
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 9
• Exact Mass: 435.18931688
• Heavy Atom Count: 31
• Complexity: 576

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)NCC(COC1=CC=CC2=CC=CC=C21)OC3C(C(C(C(O3)C(=O)O)O)O)O
• Isomeric SMILES: CC(C)NC[C@@H](COC1=CC=CC2=CC=CC=C21)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)C(=O)O)O)O)O

Technology Process of (s)-Propranolol glucuronide

There total 2 articles about (s)-Propranolol 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:

methyl <1-(1'-naphthoxy)-3-azido-2-propyl-2,3,4-tri-O-acetyl-β-D-glucopyranosid>uronate → (S)-propranolol β-D-glucuronide (58657-78-6)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂ / PtO₂ / ethanol / 8 h / 1551.4 Torr

2: 590 mg / NaOMe / methanol / 0.67 h / Ambient temperature

With hydrogen; sodium methylate; platinum(IV) oxide; In methanol; ethanol;

DOI:10.1021/jm00366a005

Reference yield:

methyl (2R)-<1-(1'-naphthoxy)-3-(isopropylamino)-2-propyl-2,3,4-tri-O-acetyl-β-D-glucopyranosid>uronate (87102-67-8) → (S)-propranolol β-D-glucuronide (58657-78-6)

Guidance literature:

With sodium methylate; In methanol; for 0.666667h; Ambient temperature;

DOI:10.1021/jm00366a005

upstream raw materials:

methyl (2R)-<1-(1'-naphthoxy)-3-(isopropylamino)-2-propyl-2,3,4-tri-O-acetyl-β-D-glucopyranosid>uronate