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4'-Demethylepipodophyllotoxin
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Name

4'-Demethylepipodophyllotoxin

 EINECS 613-823-0
CAS No. 6559-91-7 Density 1.446 g/cm3
PSA 103.68000 LogP 2.10620
Solubility N/A Melting Point 246-248 °C
Formula C21H20O8 Boiling Point 626.5 °C at 760 mmHg
Molecular Weight 400.385 Flash Point 224.4 °C
Transport Information N/A Appearance White crystalline powder
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 6559-91-7 (4'-Demethylepipodophyllotoxin) Hazard Symbols N/A
Synonyms

Epipodophyllotoxin,4'-demethyl- (7CI,8CI);Furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one,5,8,8a,9-tetrahydro-9-hydroxy-5-(4-hydroxy-3,5-dimethoxyphenyl)-, [5R-(5a,5ab,8aa,9b)]-;(-)-4'-Demethylepipodophyllotoxin;4'-Demethylepipodophyllotoxin;4'-O-demethylepipodophyllotoxin;

Article Data 36

4'-Demethylepipodophyllotoxin Synthetic route

518-28-5

podofilox

6559-91-7

4'-demethylepipodophyllotoxin

Conditions
ConditionsYield
With methanesulfonic acid; DL-methionine; trifluoroacetic acid at 40℃; for 0.75h;93%
Stage #1: podofilox With methanesulfonic acid; sodium iodide In dichloromethane at 0 - 20℃; for 5h;
Stage #2: With barium carbonate In water; acetone at 40℃; for 0.5h;		90%
Stage #1: podofilox With 1-(Trimethylsilyl)imidazole In dichloromethane at 0℃;
Stage #2: With water; barium carbonate In acetone		79%
156350-44-6

Carbonic acid benzyl ester 4-((5R,5aR,8aR)-6,9-dioxo-5,5a,6,8,8a,9-hexahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl)-2,6-dimethoxy-phenyl ester

6559-91-7

4'-demethylepipodophyllotoxin

Conditions
ConditionsYield
With ruthenium(II) chloride; (S)-N2,N2'-bis(pyridin-2-ylmethyl-1,1'-binaphthyl-2,2'-diamine); hydrogen In isopropyl alcohol at 20 - 25℃; under 38002.6 Torr; for 18h;89%
16477-16-0

4'-O-demethyl-4β-bromo-4-desoxypodophyllotoxin

6559-91-7

4'-demethylepipodophyllotoxin

Conditions
ConditionsYield
With water; barium carbonate In acetone at 40℃; for 4h;71%
With barium carbonate In water; acetone for 1h; Heating;52%
64-19-7

acetic acid

518-28-5

podofilox

A

6559-91-7

4'-demethylepipodophyllotoxin

B

102306-96-7

4'-demethyl-β-apopicropodophyllotoxin

C

102306-95-6

4'-demethyl-1-O-ethyl-1-epipodophyllotoxin

D

4375-07-9

epipodophyllotoxin

Conditions
ConditionsYield
With hydrogen bromide 1.) 15 min, 2.) RT, 20 h; Multistep reaction. Further byproducts given;
...Expand
64-19-7

acetic acid

518-28-5

podofilox

A

6559-91-7

4'-demethylepipodophyllotoxin

B

102306-96-7

4'-demethyl-β-apopicropodophyllotoxin

C

102306-97-8

3',4'-didemethylepipodophyllotoxin

D

4375-07-9

epipodophyllotoxin

Conditions
ConditionsYield
With hydrogen bromide 1.) 15 min, 2.) RT, 20 h; Multistep reaction. Further byproducts given;
...Expand
33419-42-0

etoposide

6559-91-7

4'-demethylepipodophyllotoxin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium iodide; chloro-trimethyl-silane / acetonitrile / 0 °C
2: water; barium carbonate / acetone / 20 °C
View Scheme
134-96-3

syringic aldehyde

6559-91-7

4'-demethylepipodophyllotoxin

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: sodium hydroxide / tetrahydrofuran / 25 - 30 °C
2.1: lithium diisopropyl amide / tetrahydrofuran / 3 h / -20 - -15 °C / Inert atmosphere
3.1: iron(III) chloride / dichloromethane / 1 h / 18 - 22 °C
4.1: triethylamine / dichloromethane / 1 h / -2 - 2 °C
5.1: palladium diacetate; triphenylphosphine; potassium carbonate / acetonitrile / 20 h / 75 - 85 °C
6.1: pyridine; ozone / dichloromethane; methanol / 5 h / -25 - -15 °C
6.2: 4 h / 20 °C / Inert atmosphere
7.1: (S)-N2,N2'-bis(pyridin-2-ylmethyl-1,1'-binaphthyl-2,2'-diamine); ruthenium(II) chloride; hydrogen / isopropyl alcohol / 18 h / 20 - 25 °C / 38002.6 Torr
View Scheme

C17H16O6

6559-91-7

4'-demethylepipodophyllotoxin

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: lithium diisopropyl amide / tetrahydrofuran / 3 h / -20 - -15 °C / Inert atmosphere
2.1: iron(III) chloride / dichloromethane / 1 h / 18 - 22 °C
3.1: triethylamine / dichloromethane / 1 h / -2 - 2 °C
4.1: palladium diacetate; triphenylphosphine; potassium carbonate / acetonitrile / 20 h / 75 - 85 °C
5.1: pyridine; ozone / dichloromethane; methanol / 5 h / -25 - -15 °C
5.2: 4 h / 20 °C / Inert atmosphere
6.1: (S)-N2,N2'-bis(pyridin-2-ylmethyl-1,1'-binaphthyl-2,2'-diamine); ruthenium(II) chloride; hydrogen / isopropyl alcohol / 18 h / 20 - 25 °C / 38002.6 Torr
View Scheme

C23H24O8

6559-91-7

4'-demethylepipodophyllotoxin

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: iron(III) chloride / dichloromethane / 1 h / 18 - 22 °C
2.1: triethylamine / dichloromethane / 1 h / -2 - 2 °C
3.1: palladium diacetate; triphenylphosphine; potassium carbonate / acetonitrile / 20 h / 75 - 85 °C
4.1: pyridine; ozone / dichloromethane; methanol / 5 h / -25 - -15 °C
4.2: 4 h / 20 °C / Inert atmosphere
5.1: (S)-N2,N2'-bis(pyridin-2-ylmethyl-1,1'-binaphthyl-2,2'-diamine); ruthenium(II) chloride; hydrogen / isopropyl alcohol / 18 h / 20 - 25 °C / 38002.6 Torr
View Scheme

C30H28O10

6559-91-7

4'-demethylepipodophyllotoxin

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: triethylamine / dichloromethane / 1 h / -2 - 2 °C
2.1: palladium diacetate; triphenylphosphine; potassium carbonate / acetonitrile / 20 h / 75 - 85 °C
3.1: pyridine; ozone / dichloromethane; methanol / 5 h / -25 - -15 °C
3.2: 4 h / 20 °C / Inert atmosphere
4.1: (S)-N2,N2'-bis(pyridin-2-ylmethyl-1,1'-binaphthyl-2,2'-diamine); ruthenium(II) chloride; hydrogen / isopropyl alcohol / 18 h / 20 - 25 °C / 38002.6 Torr
View Scheme

4'-Demethylepipodophyllotoxin Specification

The CAS registry number of 4'-Demethylepipodophyllotoxin is 6559-91-7. The IUPAC name is (5S,5aR,8aR,9R)-5-hydroxy-9-(4-hydroxy-3,5-dimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one. It belongs to the classes of Miscellaneous Natural Products; Plant Oils, Toxins, Phenolic Acids & Derivatives; Inhibitors. In addition, its molecular formula is C21H20O8 and the molecular weight is 400.38. Besides, it is off-white solid. And it can be used as a potent inhibitor of microtubule assembly.

Physical properties about this chemical are: (1)ACD/LogP: 0.71; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.71; (4)ACD/LogD (pH 7.4): 0.71; (5)ACD/BCF (pH 5.5): 2.05; (6)ACD/BCF (pH 7.4): 2.04; (7)ACD/KOC (pH 5.5): 58.17; (8)ACD/KOC (pH 7.4): 58; (9)H bond acceptors: 8; (10)H bond donors: 2; (11)Freely Rotating Bonds: 5; (12)Polar Surface Area: 81.68 Å2; (13)Index of Refraction: 1.637; (14)Molar Refractivity: 99.48 cm3; (15)Molar Volume: 276.8 cm3; (16)Polarizability: 39.43×10-24cm3; (17)Surface Tension: 60.3 dyne/cm; (18)Density: 1.446 g/cm3; (19)Flash Point: 224.4 °C; (20)Enthalpy of Vaporization: 97.48 kJ/mol; (21)Boiling Point: 626.5 °C at 760 mmHg; (22)Vapour Pressure: 1.46E-16 mmHg at 25 °C.

Preparation of 4'-Demethylepipodophyllotoxin: it can be prepared by 1-Brom-1-desoxy-4'-demethyl-epipodophyllotoxin. This reaction will need reagents BaCO3 and H2O and solvent acetone. The reaction time is 4 hours at reaction temperature of 40 °C. The yield is about 71%.

4'-Demethylepipodophyllotoxin can be prepared by 1-Brom-1-desoxy-4'-demethyl-epipodophyllotoxin.

Uses of 4'-Demethylepipodophyllotoxin: it can be used to get 2'-chloro-4'-O-demethylepipodophyllotoxin. This reaction will need reagent N-chlorosuccinimide and solvent dimethylformamide. The reaction time is 3.5 hours at ambient temperature. The yield is about 75%.

4'-Demethylepipodophyllotoxin can be used to get 2'-chloro-4'-O-demethylepipodophyllotoxin

People can use the following data to convert to the molecule structure.
(1)SMILES: O=C4OC[C@@H]5[C@H](O)c2cc1OCOc1cc2[C@@H](c3cc(OC)c(O)c(OC)c3)[C@@H]45
(2)InChI: InChI=1/C21H20O8/c1-25-15-3-9(4-16(26-2)20(15)23)17-10-5-13-14(29-8-28-13)6-11(10)19(22)12-7-27-21(24)18(12)17/h3-6,12,17-19,22-23H,7-8H2,1-2H3/t12-,17+,18-,19+/m0/s1
(3)InChIKey: YVCVYCSAAZQOJI-JHQYFNNDBA

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