11beta-Methoxy-5alpha-(3,5-dimethoxy-4-hydroxyphenyl)-5,6,11,11aalpha-tetrahydro-1H-oxazolo[3',4':1,6]pyrido[3,4-b]indol-3-one

Base Information

Chemical Name:11beta-Methoxy-5alpha-(3,5-dimethoxy-4-hydroxyphenyl)-5,6,11,11aalpha-tetrahydro-1H-oxazolo[3',4':1,6]pyrido[3,4-b]indol-3-one
CAS No.:177020-27-8
Molecular Formula:C₂₂H₂₂N₂O₆
Molecular Weight:410.426
Hs Code.:
DSSTox Substance ID:DTXSID401101437
Nikkaji Number:J747.577B
ChEMBL ID:CHEMBL71270

Synonyms:CHEMBL71270;DTXSID401101437;11beta-Methoxy-5alpha-(3,5-dimethoxy-4-hydroxyphenyl)-5,6,11,11aalpha-tetrahydro-1H-oxazolo[3',4':1,6]pyrido[3,4-b]indol-3-one;177020-27-8;1H,3H-Oxazolo[3',4':1,6]pyrido[3,4-b]indol-3-one, 5,6,11,11a-tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl)-11-methoxy-, [5R-(5alpha,11beta,11aalpha)]-

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Chemical Property of 11beta-Methoxy-5alpha-(3,5-dimethoxy-4-hydroxyphenyl)-5,6,11,11aalpha-tetrahydro-1H-oxazolo[3',4':1,6]pyrido[3,4-b]indol-3-one

Chemical Property:

XLogP3:2.4
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:4
Exact Mass:410.14778643
Heavy Atom Count:30
Complexity:635

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

Useful:

Canonical SMILES:COC1C2COC(=O)N2C(C3=C1C4=CC=CC=C4N3)C5=CC(=C(C(=C5)OC)O)OC
Isomeric SMILES:CO[C@H]1[C@H]2COC(=O)N2[C@@H](C3=C1C4=CC=CC=C4N3)C5=CC(=C(C(=C5)OC)O)OC

Technology Process of 11beta-Methoxy-5alpha-(3,5-dimethoxy-4-hydroxyphenyl)-5,6,11,11aalpha-tetrahydro-1H-oxazolo[3',4':1,6]pyrido[3,4-b]indol-3-one

There total 4 articles about 11beta-Methoxy-5alpha-(3,5-dimethoxy-4-hydroxyphenyl)-5,6,11,11aalpha-tetrahydro-1H-oxazolo[3',4':1,6]pyrido[3,4-b]indol-3-one 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: 47.0%

: 66460-63-7
4-Hydroxy-3,5-dimethoxy-benzaldehyd-dimethylacetal

: Acetic acid (1H-indol-3-yl)-((R)-2-oxo-oxazolidin-4-yl)-methyl ester

: 177020-27-8
(3aR,4R,10R)-10-(4-Hydroxy-3,5-dimethoxy-phenyl)-4-methoxy-3a,4,9,10-tetrahydro-3H-2-oxa-9,10a-diaza-cyclopenta[b]fluoren-1-one

Guidance literature:: With toluene-4-sulfonic acid; In methanol; dichloromethane; for 4h;
DOI:10.1021/jm9508806

Reference yield:

: 152153-01-0,157636-81-2
(S)-4-[(1H-indol-3-yl)methyl]oxazolidin-2-one

: 177020-27-8
(3aR,4R,10R)-10-(4-Hydroxy-3,5-dimethoxy-phenyl)-4-methoxy-3a,4,9,10-tetrahydro-3H-2-oxa-9,10a-diaza-cyclopenta[b]fluoren-1-one

Guidance literature:: Multi-step reaction with 2 steps

1: 98 percent / DDQ / tetrahydrofuran / 1.) -78 deg C, 30 min, 2.) RT, 24 h

2: 47 percent / p-TsOH / CH₂Cl₂; methanol / 4 h

With toluene-4-sulfonic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/jm9508806

Reference yield:

: 134-96-3
syringic aldehyde

: 177020-27-8
(3aR,4R,10R)-10-(4-Hydroxy-3,5-dimethoxy-phenyl)-4-methoxy-3a,4,9,10-tetrahydro-3H-2-oxa-9,10a-diaza-cyclopenta[b]fluoren-1-one

Guidance literature:: Multi-step reaction with 2 steps

1: p-TsOH

2: 47 percent / p-TsOH / CH₂Cl₂; methanol / 4 h

With toluene-4-sulfonic acid; In methanol; dichloromethane;
DOI:10.1021/jm9508806