(8alpha,9R)-10,11-Dihydro-6'-methoxycinchonan-9,10,11-triol

Base Information

• Chemical Name: (8alpha,9R)-10,11-Dihydro-6'-methoxycinchonan-9,10,11-triol
• CAS No.: 78549-62-9
• Molecular Formula: C₂₀H₂₆N₂O₄
• Molecular Weight: 358.437
• DSSTox Substance ID: DTXSID201204041
• Mol file: 78549-62-9.mol

Synonyms:DTXSID201204041;(8alpha,9R)-10,11-Dihydro-6'-methoxycinchonan-9,10,11-triol;78549-62-9

Chemical Property of (8alpha,9R)-10,11-Dihydro-6'-methoxycinchonan-9,10,11-triol

Chemical Property:

• XLogP3: 0.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 358.18925731
• Heavy Atom Count: 26
• Complexity: 479

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC1=CC2=C(C=CN=C2C=C1)C(C3CC4CCN3CC4C(CO)O)O
• Isomeric SMILES: COC1=CC2=C(C=CN=C2C=C1)[C@H]([C@@H]3C[C@@H]4CCN3C[C@@H]4C(CO)O)O

Technology Process of (8alpha,9R)-10,11-Dihydro-6'-methoxycinchonan-9,10,11-triol

There total 4 articles about (8alpha,9R)-10,11-Dihydro-6'-methoxycinchonan-9,10,11-triol 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:

(S)-[(1S,4S,5R)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-1-aza-bicyclo[2.2.2]oct-2-yl]-(6-methoxy-quinolin-4-yl)-methanol (111726-40-0,111726-41-1) → (R)-1-{(1S,3R,4S)-6-[(S)-Hydroxy-(6-methoxy-quinolin-4-yl)-methyl]-1-aza-bicyclo[2.2.2]oct-3-yl}-ethane-1,2-diol (73489-79-9,73489-80-2,73522-65-3,73522-91-5,78549-62-9,80227-26-5)

Guidance literature:

With IR 120-H⁺ resin; In methanol;

DOI:10.1139/v87-448

Reference yield:

(S)-[(1S,4S,5R)-5-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-1-aza-bicyclo[2.2.2]oct-2-yl]-(6-methoxy-quinolin-4-yl)-methanol (111726-40-0,111726-41-1) → (S)-1-{(1S,3R,4S)-6-[(S)-Hydroxy-(6-methoxy-quinolin-4-yl)-methyl]-1-aza-bicyclo[2.2.2]oct-3-yl}-ethane-1,2-diol (73489-79-9,73489-80-2,73522-65-3,73522-91-5,78549-62-9,80227-26-5)

Guidance literature:

With IR 120-H⁺ resin; In methanol;

DOI:10.1139/v87-448

Reference yield:

d'acetylquinidine (18797-86-9,56652-53-0) → (S)-1-{(1S,3R,4S)-6-[(S)-Hydroxy-(6-methoxy-quinolin-4-yl)-methyl]-1-aza-bicyclo[2.2.2]oct-3-yl}-ethane-1,2-diol (73489-79-9,73489-80-2,73522-65-3,73522-91-5,78549-62-9,80227-26-5)

Guidance literature:

Multi-step reaction with 2 steps

2: 343 mg / IR 120-H⁺ resin / methanol

With IR 120-H⁺ resin; In methanol;

DOI:10.1139/v87-448

upstream raw materials:

(S)-[(1S,4S,5R)-5-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-1-aza-bicyclo[2.2.2]oct-2-yl]-(6-methoxy-quinolin-4-yl)-methanol

d'acetylquinidine

(S)-[(1S,4S,5R)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-1-aza-bicyclo[2.2.2]oct-2-yl]-(6-methoxy-quinolin-4-yl)-methanol