(5S,5aS,8aR,9R)-9-(4-hydroxy-3,5-dimethoxyphenyl)-5-(4-nitroanilino)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one

Base Information

Chemical Name:(5S,5aS,8aR,9R)-9-(4-hydroxy-3,5-dimethoxyphenyl)-5-(4-nitroanilino)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one
CAS No.:127882-73-9
Molecular Formula:C27H24 N2 O9
Molecular Weight:520.496
Hs Code.:
UNII:0I81858VSZ
DSSTox Substance ID:DTXSID40155689
Nikkaji Number:J342.017E
Wikidata:Q27236812
Pharos Ligand ID:T4X3KCDPMBCJ
ChEMBL ID:CHEMBL283631
Mol file:127882-73-9.mol

Synonyms:furo(3',4':6,7)naphtho(2,3-d)-1,3-dioxol-6(5aH)-one, 5,8,8a,9-tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl)-9-((4-nitrophenyl)amino)-, (5R,5aR,8aS,9S)-;GL 331;GL-331;GL331

Suppliers and Price of (5S,5aS,8aR,9R)-9-(4-hydroxy-3,5-dimethoxyphenyl)-5-(4-nitroanilino)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
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price

Total 2 raw suppliers

Chemical Property of (5S,5aS,8aR,9R)-9-(4-hydroxy-3,5-dimethoxyphenyl)-5-(4-nitroanilino)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one

Chemical Property:

XLogP3:3.9
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:10
Rotatable Bond Count:5
Exact Mass:520.14818035
Heavy Atom Count:38
Complexity:863

Purity/Quality:: 98%min ^*data from raw suppliers

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:: SDS file from LookChem

Useful:

Canonical SMILES:COC1=CC(=CC(=C1O)OC)C2C3C(COC3=O)C(C4=CC5=C(C=C24)OCO5)NC6=CC=C(C=C6)[N+](=O)[O-]
Isomeric SMILES:COC1=CC(=CC(=C1O)OC)[C@H]2[C@@H]3[C@H](COC3=O)[C@@H](C4=CC5=C(C=C24)OCO5)NC6=CC=C(C=C6)[N+](=O)[O-]

Technology Process of (5S,5aS,8aR,9R)-9-(4-hydroxy-3,5-dimethoxyphenyl)-5-(4-nitroanilino)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one

There total 6 articles about (5S,5aS,8aR,9R)-9-(4-hydroxy-3,5-dimethoxyphenyl)-5-(4-nitroanilino)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-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: 44.0%

: 16477-16-0
4'-O-demethyl-4β-bromo-4-desoxypodophyllotoxin

: 100-01-6,104810-17-5
4-nitro-aniline

: 127882-73-9
4'-O-demethyl-4β-(4''-nitroanilino)-4-desoxypodophyllotoxin

Guidance literature:: With barium carbonate; In 1,2-dichloro-ethane; Ambient temperature;
DOI:10.1021/jm00171a050

Reference yield:

: 100-01-6,104810-17-5
4-nitro-aniline

: 746639-24-7
4β-iodo-4-O-demethylpodophyllotoxin

: 127882-73-9
4'-O-demethyl-4β-(4''-nitroanilino)-4-desoxypodophyllotoxin

Guidance literature:: With barium carbonate; In tetrahydrofuran; at 20 ℃; for 8h;
DOI:10.1016/S0960-894X(00)00407-8

Reference yield:

: 6559-91-7
4'-demethylepipodophyllotoxin

: 127882-73-9
4'-O-demethyl-4β-(4''-nitroanilino)-4-desoxypodophyllotoxin

Guidance literature:: Multi-step reaction with 2 steps

1: HBr / CH₂Cl₂; diethyl ether / 0.75 h / 0 °C

2: Et₃N, Bu₄N⁽¹⁺⁾*I^(1-) / tetrahydrofuran / 6 h / 25 - 35 °C

With hydrogen bromide; tetra-(n-butyl)ammonium iodide; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1016/0040-4039(96)00546-1