(R)-laudanosine

Base Information

• Chemical Name: (R)-laudanosine
• CAS No.: 85-63-2
• Molecular Formula: C21H27NO4
• Molecular Weight: 357.45
• UNII: EO6NL5AZ5Z
• Nikkaji Number: J430.265F
• Wikidata: Q105140900
• Metabolomics Workbench ID: 123718
• ChEMBL ID: CHEMBL1613
• Mol file: 85-63-2.mol

Synonyms:(R)-laudanosine;(-)-Laudanosine;85-63-2;D-Laudanosine;O-Methyllaudanidine;Laudanosine, (R)-;EO6NL5AZ5Z;UNII-EO6NL5AZ5Z;(R)-Laudanosine [USP];(1R)-1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-2-methyl-3,4-dihydro-1H-isoquinoline;(R)-1,2,3,4-Tetrahydro-6,7-dimethoxy-2-methyl-1-veratrylisoquinoline;Isoquinoline, 1-((3,4-dimethoxyphenyl)methyl)-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-, (1R)-;(1R)-1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline;(R)-N-methyltetrahydropapaverine;(R)-(-)-laudanosine;CHEMBL1613;SCHEMBL6130845;CHEBI:136734;KGPAYJZAMGEDIQ-QGZVFWFLSA-N;(R)-LAUDANOSINE [USP IMPURITY];CISATRACURIUM BESILATE IMPURITY C [EP IMPURITY];(1R)-6,7-Dimethoxy-1-[(3,4-dimethoxyphenyl)methyl]-2-methyl-1,2,3,4-tetrahydroisoquinoline

Chemical Property of (R)-laudanosine

Chemical Property:

• XLogP3: 3.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 357.19400834
• Heavy Atom Count: 26
• Complexity: 434

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1CCC2=CC(=C(C=C2C1CC3=CC(=C(C=C3)OC)OC)OC)OC
• Isomeric SMILES: CN1CCC2=CC(=C(C=C2[C@H]1CC3=CC(=C(C=C3)OC)OC)OC)OC

Technology Process of (R)-laudanosine

There total 46 articles about (R)-laudanosine 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: 95.51%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + (-) N-norlaudanosine (50896-90-7) → (R)-laudanosine (85-63-2,20412-65-1)

Guidance literature:

formaldehyd; (-) N-norlaudanosine; With disodium hydrogen phosphite pentahydrate; In tetrahydrofuran; Reflux;

With (R)-Mandelic Acid; In methanol; Reflux;

Reference yield: 77.0%

(-) N-norlaudanosine (50896-90-7) + dimethyl dicarbonate (4525-33-1) → (R)-laudanosine (85-63-2,20412-65-1)

Guidance literature:

(-) N-norlaudanosine; dimethyl dicarbonate; In dichloromethane; at 20 ℃; for 0.333333h;

With lithium aluminium tetrahydride; In diethyl ether; at 0 ℃; for 0.333333h; Further stages.;

DOI:10.1021/jo001397s

Reference yield:

N-[((1R,2S,5R)-8-phenylmenthoxy)carbonyl]-1-(4,5-dimethoxybenzyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline (136114-05-1,136114-06-2) → (-)-8-phenylmenthol (65253-04-5) + (S)-laudanosine (2688-77-9,20412-65-1) + (R)-laudanosine (85-63-2,20412-65-1)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; Title compound not separated from byproducts; Heating;

DOI:10.1016/S0040-4020(97)01018-1

upstream raw materials:

laudanosine

N-[((1R,2S,5R)-8-phenylmenthoxy)carbonyl]-1-(4,5-dimethoxybenzyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline

(Z)-1-<(3,4-Dimethoxyphenyl)methylene>-2-formyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline

2-[(4S)-4,5-dihydro-4-(1-methylethyl)-2-oxazolyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline

Downstream raw materials:

(-)-(R)-glaucine

2'-(β-N-Methyl-N-ethoxycarbonyl)aminoethyl-3,3',4,4'-tetramethoxystilben