Podophyllotoxin supplier | CasNO.518-28-5

Name
(5R,5aR,8aR,9R)-5,8,8a,9-Tetrahydro-9-hydroxy-5-(3,4,5-trimethoxyphenyl)-furo(3',4':6,7)naphtho[2,3-d]-1,3-dioxol-6(5aH)-one
EINECS 208-250-4
CAS No. 518-28-5
Article Data43
CAS DataBase
Density 1.37 g/cm³
Solubility
Melting Point 183-184 °C(lit.)
Formula C₂₂H₂₂O₈
Boiling Point 597.92 °C at 760 mmHg
Molecular Weight 414.412
Flash Point 210.181 °C
Transport Information UN 3462 6.1/PG 2
Appearance off-white fine crystalline powder
Safety 36/37/39-45-26
Risk Codes 21-25-36/37/38-23/25-23/24/25
Molecular Structure
Hazard Symbols T
Synonyms Podophyllinic acid lactone;(5R,5aR,8aR,9R)-5,8,8a,9-Tetrahydro-9-hydroxy-5-(3,4,5-trimethoxyphenyl)-furo(3',4':6,7)naphtho[2,3-d]-1,3-dioxol-6(5aH)-one;
PSA 92.68000
LogP 2.40920

Synthetic route

: 477-48-5, 477-49-6, 55515-07-6, 60660-51-7, 64550-42-1, 64937-82-2, 86594-36-7, 130322-38-2
podophyllotoxone

: 518-28-5
podofilox

Conditions

Conditions	Yield
With L-Selectride In tetrahydrofuran at -78℃; for 0.25h;	93%
With L-Selectride In tetrahydrofuran at -78℃; for 1.5h; Inert atmosphere;	87%
With lithium tri-t-butoxyaluminum hydride In diethyl ether at -78 - 20℃; for 18h; optical yield given as %de; diastereoselective reaction;	79%
With L-Selectride In tetrahydrofuran at -78℃; for 2h; Inert atmosphere;	70%

: 1256-91-3
(5R,6R,7R,8R)-methyl 8-hydroxy-7-(hydroxymethyl)-5-(3,4,5-trimethoxyphenyl)-5,6,7,8-tetrahydronaphtho[2,3-d][1,3]dioxole-6-carboxylate

: 518-28-5
podofilox

Conditions

Conditions	Yield
With 4 A molecular sieve; zinc(II) chloride In tetrahydrofuran at 64℃; for 2.5h;	85%
With molecular sieve; zinc(II) chloride In tetrahydrofuran	75%
With 4 A molecular sieve; zinc(II) chloride In tetrahydrofuran for 2.5h; Heating; Yield given;

: 261158-30-9
(1R,2R,3R,4R)-4-O-(2'-trimethylsilylethoxy)methylpodophyllotoxin

: 518-28-5
podofilox

Conditions

Conditions	Yield
With ethanethiol; magnesium bromide In diethyl ether; benzene at 0 - 20℃; for 11h; SEM deprotection;	81%

: 112711-16-7
(5R,5aR,8aR,9R)-9-((tert-butyldimethylsilyl)oxy)-5-(3,4,5-trimethoxyphenyl)-5,8,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one

: 518-28-5
podofilox

Conditions

Conditions	Yield
With triethylamine hydrofluoride In acetonitrile for 72h; Ambient temperature;	79%
With tetrabutyl ammonium fluoride; acetic acid In tetrahydrofuran at 0℃; for 2h; Inert atmosphere;	54%

: 563-80-4
3-methyl-butan-2-one

: 477-48-5, 477-49-6, 55515-07-6, 60660-51-7, 64550-42-1, 64937-82-2, 86594-36-7, 130322-38-2
podophyllotoxone

A: 7α-[(2R)-2-hydroxy-3-methylbut-2-yl]epi-podophyllotoxin

B: 7α-[(2S)-2-hydroxy-3-methylbut-2-yl]epi-podophyllotoxin

C: 477-51-0, 6258-33-9, 17187-81-4, 17301-90-5, 19186-35-7, 24150-39-8, 31892-96-3, 55568-81-5, 64550-41-0, 69222-20-4, 75171-57-2, 83023-41-0, 100348-38-7
deoxypodophyllotoxin

D: 518-28-5
podofilox

Conditions

Conditions	Yield
With titanium tetrachloride; zinc In tetrahydrofuran at -20 - -10℃; for 4h; McMurry reaction; Inert atmosphere;	A 45% B 9% C n/a D n/a

...Expand

: 67-64-1
acetone

: 477-48-5, 477-49-6, 55515-07-6, 60660-51-7, 64550-42-1, 64937-82-2, 86594-36-7, 130322-38-2
podophyllotoxone

A: 7α-(2-hydroxyprop-2-yl)podophyllotoxin

B: 7β-(2-hydroxyprop-2-yl)podophyllotoxin

C: 477-51-0, 6258-33-9, 17187-81-4, 17301-90-5, 19186-35-7, 24150-39-8, 31892-96-3, 55568-81-5, 64550-41-0, 69222-20-4, 75171-57-2, 83023-41-0, 100348-38-7
deoxypodophyllotoxin

D: 518-28-5
podofilox

Conditions

Conditions	Yield
With titanium tetrachloride; zinc In tetrahydrofuran at -20 - -10℃; for 4h; McMurry reaction; Inert atmosphere; optical yield given as %de;	A 45% B 9% C n/a D n/a

...Expand

: C32H35NO8S

A: 4375-07-9
epipodophyllotoxin

B: 518-28-5
podofilox

Conditions

Conditions	Yield
With trifluoroacetic acid In tetrahydrofuran; water at 0 - 25℃; for 27h; Inert atmosphere;	A 33% B 43%
With trifluoroacetic acid In tetrahydrofuran; water at 0 - 20℃; for 24h; Overall yield = 76 %; Overall yield = 43 mg;

: 1191-95-3
cyclobutanone

: 477-48-5, 477-49-6, 55515-07-6, 60660-51-7, 64550-42-1, 64937-82-2, 86594-36-7, 130322-38-2
podophyllotoxone

A: 1391928-23-6
7α-(1-hydroxycyclobutyl)epi-podophyllotoxin

B: 477-51-0, 6258-33-9, 17187-81-4, 17301-90-5, 19186-35-7, 24150-39-8, 31892-96-3, 55568-81-5, 64550-41-0, 69222-20-4, 75171-57-2, 83023-41-0, 100348-38-7
deoxypodophyllotoxin

C: 518-28-5
podofilox

Conditions

Conditions	Yield
With titanium tetrachloride; zinc In tetrahydrofuran at -20 - -10℃; for 4h; McMurry reaction; Inert atmosphere;	A 40% B n/a C n/a

...Expand

: 108-94-1
cyclohexanone

: 477-48-5, 477-49-6, 55515-07-6, 60660-51-7, 64550-42-1, 64937-82-2, 86594-36-7, 130322-38-2
podophyllotoxone

A: 7α-(1-hydroxycyclohexyl)podophyllotoxin

B: 7β-(1-hydroxycyclohexyl)podophyllotoxin

C: 477-51-0, 6258-33-9, 17187-81-4, 17301-90-5, 19186-35-7, 24150-39-8, 31892-96-3, 55568-81-5, 64550-41-0, 69222-20-4, 75171-57-2, 83023-41-0, 100348-38-7
deoxypodophyllotoxin

D: 518-28-5
podofilox

Conditions

Conditions	Yield
With titanium tetrachloride; zinc In tetrahydrofuran at -20 - -10℃; for 4h; McMurry reaction; Inert atmosphere; optical yield given as %de;	A 40% B 7% C n/a D n/a

...Expand

: 120-92-3
cyclopentanone

: 477-48-5, 477-49-6, 55515-07-6, 60660-51-7, 64550-42-1, 64937-82-2, 86594-36-7, 130322-38-2
podophyllotoxone

A: 7α-(1-hydroxycyclopentyl)epi-podophyllotoxin

B: 7β-(1-hydroxycyclopentyl)podophyllotoxin

C: 477-51-0, 6258-33-9, 17187-81-4, 17301-90-5, 19186-35-7, 24150-39-8, 31892-96-3, 55568-81-5, 64550-41-0, 69222-20-4, 75171-57-2, 83023-41-0, 100348-38-7
deoxypodophyllotoxin

D: 518-28-5
podofilox

Conditions

Conditions	Yield
With titanium tetrachloride; zinc In tetrahydrofuran at -20 - -10℃; for 4h; McMurry reaction; Inert atmosphere; optical yield given as %de;	A 40% B 8% C n/a D n/a

...Expand

: 29943-42-8
Tetrahydro-4H-pyran-4-one

: 477-48-5, 477-49-6, 55515-07-6, 60660-51-7, 64550-42-1, 64937-82-2, 86594-36-7, 130322-38-2
podophyllotoxone

A: 7α-(4-hydroxytetrahydropyran-4-yl)podophyllotoxin

B: 7β-(4-hydroxytetrahydropyran-4-yl)podophyllotoxin

C: 477-51-0, 6258-33-9, 17187-81-4, 17301-90-5, 19186-35-7, 24150-39-8, 31892-96-3, 55568-81-5, 64550-41-0, 69222-20-4, 75171-57-2, 83023-41-0, 100348-38-7
deoxypodophyllotoxin

D: 518-28-5
podofilox

Conditions

Conditions	Yield
With titanium tetrachloride; zinc In tetrahydrofuran at -20 - -10℃; for 4h; McMurry reaction; Inert atmosphere; optical yield given as %de;	A 38% B 15% C n/a D n/a

...Expand

: 100-50-5
3-Cyclohexene-1-carboxaldehyde

: 477-48-5, 477-49-6, 55515-07-6, 60660-51-7, 64550-42-1, 64937-82-2, 86594-36-7, 130322-38-2
podophyllotoxone

A: 7α-[(1R)-1-cyclohex-3-enyl-1-hydroxymethyl]epi-podophyllotoxin

B: 7α-[(1S)-1-cyclohex-3-enyl-1-hydroxymethyl]epi-podophyllotoxin

C: 477-51-0, 6258-33-9, 17187-81-4, 17301-90-5, 19186-35-7, 24150-39-8, 31892-96-3, 55568-81-5, 64550-41-0, 69222-20-4, 75171-57-2, 83023-41-0, 100348-38-7
deoxypodophyllotoxin

D: 518-28-5
podofilox

Conditions

Conditions	Yield
With titanium tetrachloride; zinc In tetrahydrofuran at -20 - -10℃; for 4h; McMurry reaction; Inert atmosphere;	A 38% B 9% C n/a D n/a

...Expand

: 119-61-9
benzophenone

: 477-48-5, 477-49-6, 55515-07-6, 60660-51-7, 64550-42-1, 64937-82-2, 86594-36-7, 130322-38-2
podophyllotoxone

A: 7α-(1-hydroxy-1,1-diphenylmethyl)epi-podophyllotoxin

B: 7β-(1-hydroxy-1,1-diphenylmethyl)podophyllotoxin

C: 477-51-0, 6258-33-9, 17187-81-4, 17301-90-5, 19186-35-7, 24150-39-8, 31892-96-3, 55568-81-5, 64550-41-0, 69222-20-4, 75171-57-2, 83023-41-0, 100348-38-7
deoxypodophyllotoxin

D: 518-28-5
podofilox

Conditions

Conditions	Yield
With titanium tetrachloride; zinc In tetrahydrofuran at -20 - -10℃; for 4h; McMurry reaction; Inert atmosphere; optical yield given as %de;	A 35% B 5% C n/a D n/a

...Expand

: 17931-55-4
bicyclo[3.3.1]nonan-9-one

: 477-48-5, 477-49-6, 55515-07-6, 60660-51-7, 64550-42-1, 64937-82-2, 86594-36-7, 130322-38-2
podophyllotoxone

A: 7α-(9-hydroxybicyclo[3.3.1]non-9-yl)podophyllotoxin

B: 7β-(9-hydroxybicyclo[3.3.1]non-9-yl)podophyllotoxin

C: 477-51-0, 6258-33-9, 17187-81-4, 17301-90-5, 19186-35-7, 24150-39-8, 31892-96-3, 55568-81-5, 64550-41-0, 69222-20-4, 75171-57-2, 83023-41-0, 100348-38-7
deoxypodophyllotoxin

D: 518-28-5
podofilox

Conditions

Conditions	Yield
With titanium tetrachloride; zinc In tetrahydrofuran at -20 - -10℃; for 4h; McMurry reaction; Inert atmosphere; optical yield given as %de;	A 30% B 20% C n/a D n/a

...Expand

: 75-07-0
acetaldehyde

: 77-76-9
2,2-dimethoxy-propane

: 477-48-5, 477-49-6, 55515-07-6, 60660-51-7, 64550-42-1, 64937-82-2, 86594-36-7, 130322-38-2
podophyllotoxone

A: 7α-([(1S)-1-hydroxyethyl]-2,2,5-trimethyl-1,3-dioxolan-4-yl)epi-podophyllotoxin acetonide

B: 7α-([(1R)-1-hydroxyethyl]-2,2,5-trimethyl-1,3-dioxolan-4-yl)epi-podophyllotoxin acetonide

C: 477-51-0, 6258-33-9, 17187-81-4, 17301-90-5, 19186-35-7, 24150-39-8, 31892-96-3, 55568-81-5, 64550-41-0, 69222-20-4, 75171-57-2, 83023-41-0, 100348-38-7
deoxypodophyllotoxin

D: 518-28-5
podofilox

Conditions

Conditions	Yield
Stage #1: acetaldehyde; podophyllotoxone With titanium tetrachloride; zinc In tetrahydrofuran at -20 - -10℃; for 4h; McMurry reaction; Inert atmosphere; Stage #2: 2,2-dimethoxy-propane With chloro-trimethyl-silane In acetone for 0.0833333h; Inert atmosphere;	A 15% B 30% C n/a D n/a

...Expand

: 123-72-8
butyraldehyde

: 477-48-5, 477-49-6, 55515-07-6, 60660-51-7, 64550-42-1, 64937-82-2, 86594-36-7, 130322-38-2
podophyllotoxone

A: 7α-[(1R)-1-hydroxybutyl]epi-podophyllotoxin

B: 7α-[(1S)-1-hydroxybutyl]epi-podophyllotoxin

C: 477-51-0, 6258-33-9, 17187-81-4, 17301-90-5, 19186-35-7, 24150-39-8, 31892-96-3, 55568-81-5, 64550-41-0, 69222-20-4, 75171-57-2, 83023-41-0, 100348-38-7
deoxypodophyllotoxin

D: 518-28-5
podofilox

Conditions

Conditions	Yield
With titanium tetrachloride; zinc In tetrahydrofuran at -20 - -10℃; for 4h; McMurry reaction; Inert atmosphere;	A 30% B 8% C n/a D n/a

...Expand

: 1131-62-0
1-(3,4-dimethoxyphenyl)ethanone

: 477-48-5, 477-49-6, 55515-07-6, 60660-51-7, 64550-42-1, 64937-82-2, 86594-36-7, 130322-38-2
podophyllotoxone

A: 1391928-22-5
7α-[(1R)-1-hydroxy-1-(3,4-dimethoxyphenyl)ethyl]epi-podophyllotoxin

B: 477-51-0, 6258-33-9, 17187-81-4, 17301-90-5, 19186-35-7, 24150-39-8, 31892-96-3, 55568-81-5, 64550-41-0, 69222-20-4, 75171-57-2, 83023-41-0, 100348-38-7
deoxypodophyllotoxin

C: 518-28-5
podofilox

Conditions

Conditions	Yield
With titanium tetrachloride; zinc In tetrahydrofuran at -20 - -10℃; for 4h; McMurry reaction; Inert atmosphere;	A 30% B n/a C n/a

...Expand

: 1072-72-6
Tetrahydrothiopyran-4-one

: 477-48-5, 477-49-6, 55515-07-6, 60660-51-7, 64550-42-1, 64937-82-2, 86594-36-7, 130322-38-2
podophyllotoxone

A: 7α-(4-hydroxytetrahydrothiopyran-4-yl)epi-podophyllotoxin

B: 477-51-0, 6258-33-9, 17187-81-4, 17301-90-5, 19186-35-7, 24150-39-8, 31892-96-3, 55568-81-5, 64550-41-0, 69222-20-4, 75171-57-2, 83023-41-0, 100348-38-7
deoxypodophyllotoxin

C: 518-28-5
podofilox

Conditions

Conditions	Yield
With titanium tetrachloride; zinc In tetrahydrofuran at -20 - -10℃; for 4h; McMurry reaction; Inert atmosphere;	A 15% B n/a C n/a

...Expand

: 477-51-0, 6258-33-9, 17187-81-4, 17301-90-5, 19186-35-7, 24150-39-8, 31892-96-3, 55568-81-5, 64550-41-0, 69222-20-4, 75171-57-2, 83023-41-0, 100348-38-7
deoxypodophyllotoxin

A: 477-48-5, 477-49-6, 55515-07-6, 60660-51-7, 64550-42-1, 64937-82-2, 86594-36-7, 130322-38-2
podophyllotoxone

B: 518-28-5
podofilox

Conditions

Conditions	Yield
In dimethyl sulfoxide for 72h; Forsythia intermedia; Yields of byproduct given;	A 6% B n/a

: 16481-54-2
podophyllotoxin-7′-O-β-D-glucopyranoside

: 518-28-5
podofilox

Conditions

Conditions	Yield
With emulsin-substance

: 186581-53-3, 908094-01-9
diazomethane

: 40505-27-9
4-demethylpodophyllotoxin

: 518-28-5
podofilox

Conditions

Conditions	Yield
With methanol; diethyl ether; acetone
In methanol; diethyl ether; acetone for 24h; Ambient temperature;	20 mg

: 1180-34-3
podophyllotoxinyl acetate

A: 477-48-5
(5aR,8aS,9R)-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxole-5,8-dione

B: 477-48-5, 477-49-6, 55515-07-6, 60660-51-7, 64550-42-1, 64937-82-2, 86594-36-7, 130322-38-2
podophyllotoxone

C: 518-28-5
podofilox

Conditions

Conditions	Yield
In dimethyl sulfoxide for 72h; Forsythia intermedia; Yield given. Yields of byproduct given;

...Expand

: 16481-54-2
podophyllotoxin-7′-O-β-D-glucopyranoside

A: 477-48-5, 477-49-6, 55515-07-6, 60660-51-7, 64550-42-1, 64937-82-2, 86594-36-7, 130322-38-2
podophyllotoxone

B: 518-28-5
podofilox

Conditions

Conditions	Yield
In dimethyl sulfoxide for 72h; Forsythia intermedia; Yield given. Yields of byproduct given;

: 477-51-0, 6258-33-9, 17187-81-4, 17301-90-5, 19186-35-7, 24150-39-8, 31892-96-3, 55568-81-5, 64550-41-0, 69222-20-4, 75171-57-2, 83023-41-0, 100348-38-7
deoxypodophyllotoxin

: 518-28-5
podofilox

Conditions

Conditions	Yield
With aspergillus niger sp In ethanol for 72h;
Multi-step reaction with 3 steps 1: N-Bromosuccinimide / 1,4-dioxane / 0.33 h / 20 °C / Inert atmosphere; Schlenk technique; Irradiation 2: dipyridinium dichromate / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere 3: L-Selectride / tetrahydrofuran / 1.5 h / -78 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: chromium(VI) oxide; 3,5-dimethyl-1H-pyrazole / dichloromethane / 2 h / 0 °C 2: L-Selectride / tetrahydrofuran / 0.25 h / -78 °C View Scheme

: 477-48-5, 477-49-6, 55515-07-6, 60660-51-7, 64550-42-1, 64937-82-2, 86594-36-7, 130322-38-2
podophyllotoxone

A: 4375-07-9
epipodophyllotoxin

B: 518-28-5
podofilox

Conditions

Conditions	Yield
With zinc(II) tetrahydroborate In diethyl ether; benzene for 3.5h; Product distribution; Ambient temperature; different reducing agents, solvents, reaction temperatures and times;
With zinc(II) tetrahydroborate In diethyl ether; benzene for 3.5h; Ambient temperature; Yield given. Yields of byproduct given;

: 7401-22-1
9-Chloro-9-desoxypodophyllotoxin

A: 155252-34-9
4β-azido-4-deoxypodophyllotoxin

B: 155325-17-0
4'-O-trimethyl-4-azido-4-desoxypodophyllotoxin

C: 4375-07-9
epipodophyllotoxin

D: 518-28-5
podofilox

Conditions

Conditions	Yield
With sodium azide In water; acetone at 50℃; for 5h; Yield given. Yields of byproduct given;

...Expand

: (3S,4R)-4-(Benzenesulfinyl-benzo[1,3]dioxol-5-yl-methyl)-3-[hydroxy-(3,4,5-trimethoxy-phenyl)-methyl]-dihydro-furan-2-one

: 518-28-5
podofilox

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate; mercury(II) oxide for 28h; Yield given;

: 7647-01-0
hydrogenchloride

: 67-64-1
acetone

: 4375-07-9
epipodophyllotoxin

: 518-28-5
podofilox

...Expand

: 7647-01-0
hydrogenchloride

: 78178-41-3
podophyllinic acid hydrazide

: 518-28-5
podofilox

: 123-75-1
pyrrolidine

: 518-28-5
podofilox

: 291272-81-6
picropodophyllic acid pyrrolidinyl amide

Conditions

Conditions	Yield
In benzene at 50℃; for 46h; Inert atmosphere;	100%

: 75-04-7
ethylamine

: 518-28-5
podofilox

: 116606-76-9
N-ethyl picropodophyllamide

Conditions

Conditions	Yield
In water for 1.5h; Reflux;	100%

: 518-28-5
podofilox

: 1449601-57-3
2’-chloropodophyllotoxin

Conditions

Conditions	Yield
With N-chloro-succinimide; 2,2,6,6-tetramethylpiperidin-1-oxoammonium trifluoromethanesulfonate In chloroform at 25℃; for 12h; Reagent/catalyst; Schlenk technique;	99%
With N-chloro-succinimide In N,N-dimethyl-formamide at 0 - 20℃; for 20h;	85%
With N-chloro-succinimide at 0 - 20℃; for 24h;	85%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 518-28-5
podofilox

: 112711-16-7
(5R,5aR,8aR,9R)-9-((tert-butyldimethylsilyl)oxy)-5-(3,4,5-trimethoxyphenyl)-5,8,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one

Conditions

Conditions	Yield
With 1H-imidazole In N,N-dimethyl-formamide	98%
With 1H-imidazole	90%
With 1H-imidazole In N,N-dimethyl-formamide	90%

: 4179-44-6
9,12-epoxy-9,11-octadecadienoic acid

: 518-28-5
podofilox

: 4-O-podophyllotoxinyl 9,12-epoxyoctadeca-9,11-dienoate

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 2h; Esterification;	98%

: 2578-97-4, 136145-04-5, 557-58-4
trans-ximenynic acid

: 518-28-5
podofilox

: 4-O-podophyllotoxinyl octadec-11E-en-9-ynoate

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 2h; Esterification;	98%

: 2906-60-7
5,6-dithia-decanedioic acid

: 518-28-5
podofilox

: C52H54O18S2

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 2h; Inert atmosphere;	98%

: 1374991-25-9
C39H32O9

: 518-28-5
podofilox

: C49H44O15

Conditions

Conditions	Yield
With H3PC18H15PC2F6NO4S2(1-)*Au(1+) In dichloromethane at 20℃; Inert atmosphere; Green chemistry;	98%

: 69739-34-0
t-butyldimethylsiyl triflate

: 518-28-5
podofilox

: 112711-16-7
(5R,5aR,8aR,9R)-9-((tert-butyldimethylsilyl)oxy)-5-(3,4,5-trimethoxyphenyl)-5,8,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one

Conditions

Conditions	Yield
With 2,6-dimethylpyridine In dichloromethane at 0℃; silylation;	97%

: 110-15-6
succinic acid

: 518-28-5
podofilox

: C48H46O18

Conditions

Conditions	Yield
With dmap; 1,2-dichloro-ethane In dichloromethane at 20℃; for 24h; Inert atmosphere;	97%

: 1313028-09-9
ortho-(cyclopropylethynyl)benzoic acid

: 518-28-5
podofilox

: podophyllotoxin 4-O-ortho-cyclopropylethynylbenzoate

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 2h;	97%
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20 - 35℃; for 2h; Inert atmosphere;	97%

: 1338797-64-0
8-(2-adamantyloxy)-8-oxo-octanoic acid

: 518-28-5
podofilox

2-adamantyl (5R,5aR,8aR,9R)-8-oxo-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-isobenzofuro[5,6-f][1,-3]benzodioxol-5-yl suberate: 2-adamantyl (5R,5aR,8aR,9R)-8-oxo-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-isobenzofuro[5,6-f][1,-3]benzodioxol-5-yl suberate

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 12h;	97%

: 518-28-5
podofilox

Conditions

Conditions	Yield
With phosphorus tribromide In benzene for 1h; Heating;	96%
With hydrogen bromide In diethyl ether; dichloromethane at 0℃; for 48h;

: 544-70-7, 544-71-8, 872-23-1, 1839-11-8, 2540-56-9
cis-9,trans-11-octadecadienoic acid

: 518-28-5
podofilox

: 4-O-podophyllotoxinyl octadeca-9Z,11E-dienoate

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 2h; Esterification;	96%

: 11,12-E-epoxyoctadec-9-ynoic acid

: 518-28-5
podofilox

: 4-O-podophyllotoxinyl 11,12-E-epoxyoctadec-9-ynoate

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 2h; Esterification;	96%

: 1338797-64-0
8-(2-adamantyloxy)-8-oxo-octanoic acid

: 518-28-5
podofilox

: 2-adamantyl (5R,5aR,8aR,9R)-8-oxo-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-isobenzofuro[5,6-f][1,-3]benzodioxol-5-yl suberate

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 12h;	97%

: 518-28-5
podofilox

: 106636-74-2
1α-bromo-desoxypodophyllotoxin

Conditions

Conditions	Yield
With phosphorus tribromide In benzene for 1h; Heating;	96%
With hydrogen bromide In diethyl ether; dichloromethane at 0℃; for 48h;

: 518-28-5
podofilox

: 155325-17-0
4'-O-trimethyl-4-azido-4-desoxypodophyllotoxin

Conditions

Conditions	Yield
With sodium azide; trifluoroacetic acid In dichloromethane at 25℃; Cooling with ice;	96%
With sodium azide; phosphorus tribromide
Multi-step reaction with 2 steps 1: PBr3 / benzene / 1 h / Heating 2: NaN3 / dimethylformamide View Scheme

: 5241-64-5
Boc-D-Trp-OH

: 518-28-5
podofilox

: (5R,9R)-8-oxo-9-(3,4,5-trimethoxyphenyl)-5,5a,6,8,8a,9-hexahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl (tert-butoxycarbonyl)-D-tryptophanate

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 4h;	95.5%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; Inert atmosphere;	72%

: 15761-38-3
L-N-Boc-Ala

: 518-28-5
podofilox

: (5R,8aR,9R)-8-oxo-9-(3,4,5-trimethoxyphenyl)-5,5a,6,8,8a,9-hexahydrofuro[30,4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl(tert-butoxycarbonyl)alaninate

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 12h;	95.4%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 12h;	95.4%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 4h;	92.1%

: 518-28-5
podofilox

: 4375-07-9
epipodophyllotoxin

Conditions

Conditions	Yield
Stage #1: podofilox With methanesulfonic acid; sodium bromide In acetonitrile at 20℃; for 1h; Inert atmosphere; Green chemistry; Stage #2: With barium carbonate In water at 20℃; Green chemistry;	95%
Stage #1: podofilox With sodium iodide In acetonitrile for 0.0833333h; Stage #2: With boron trifluoride diethyl etherate In acetonitrile at 0 - 20℃; Stage #3: With water; barium carbonate In acetone; acetonitrile at 20℃; for 0.5h;	85%
Stage #1: podofilox With sodium iodide In acetonitrile at 20℃; for 0.0833333h; Stage #2: With boron trifluoride diethyl etherate at 0℃; for 0.25h; Stage #3: With barium carbonate In water; acetone at 20℃; for 2h;	72%

: 701-99-5
Phenoxyacetyl chloride

: 518-28-5
podofilox

: podophyllotoxinyl phenoxyacetate

Conditions

Conditions	Yield
In pyridine; benzene Ambient temperature;	95%

: 762-72-1
allyl-trimethyl-silane

: 518-28-5
podofilox

: 136723-80-3
4-deoxy-4-allyl-(epi)-podophyllotoxin

Conditions

Conditions	Yield
With 4 A molecular sieve; boron trifluoride diethyl etherate In dichloromethane at 25℃; for 4h;	95%

: 13734-36-6
N-(tert-butoxycarbonyl)sarcosine

: 518-28-5
podofilox

: (5R,8aR,9R)-8-oxo-9-(3,4,5-trimethoxyphenyl)-5,5a,6,8,8a,9-hexahydrofuro[30,4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl-N-(tertbutoxycarbonyl)-N-methylglycinate

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 4h;	94.2%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 12h;	90.3%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 12h;	90.3%

: 108-30-5
succinic acid anhydride

: 518-28-5
podofilox

: 47789-93-5
Succinylpodophyllotoxin

Conditions

Conditions	Yield
With dmap; triethylamine In chloroform at 20℃; for 1h; Inert atmosphere;	94%
With 1H-imidazole; dmap at 20℃; for 13h;	91%
With pyridine at 25℃; for 16h;	73%

: 19117-94-3
9,10-dibromooctadecanoic acid

: 518-28-5
podofilox

: 4-O-podophyllotoxinyl 9,10-dibromooctadecanoate

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 2h; Esterification;	94%

: 15761-39-4
1-(tert-butoxycarbonyl)-L-proline

: 518-28-5
podofilox

: 1-(tert-butyl)-2-((5R,8aR,9R)-8-oxo-9-(3,4,5-trimethoxyphenyl)-5,5a,6,8,8a,9-hexahydrofuro[30,4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl)pyrrolidine-1,2-dicarboxylate

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 12h;	94%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 12h;	94%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 20h;

: 1338797-61-7
7-(2-adamantyloxy)-7-oxo-heptanoic acid

: 518-28-5
podofilox

: 2-adamantyl (5R,5aR,8aR,9R)-8-oxo-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-isobenzofuro[5,6-f][1,-3]benzodioxol-5-yl pimelate

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 12h;	94%

: 897364-02-2
p-tolyl 2-O-acetyl-3,4,6-tri-O-benzyl-1-thio-β-D-galactopyranoside

: 518-28-5
podofilox

: 7-O-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)podophyllotoxin

Conditions

Conditions	Yield
With rhodium (II) octanoate dimer; 2,6-di-tert-butyl-4-methylpyridinium trifluoromethanesulfonate; methyl 2-(4-chlorophenyl)-2-diazoacetate In dichloromethane at 0℃; for 2h; Molecular sieve;	94%

: 4426-72-6, 51433-48-8
hydrazine carboxamide

: 518-28-5
podofilox

: C23H27N3O9

Conditions

Conditions	Yield
With acetic acid In methanol for 6h; Reflux;	94%

: 518-28-5
podofilox

: 78178-41-3
podophyllinic acid hydrazide

Conditions

Conditions	Yield
With acetic acid; hydrazine In methanol for 6h; Reflux;	94%

Podophyllotoxin Specification

The Furo(3',4':6,7)naphtho(2,3-d)-1,3-dioxol-6(5alphaH)-one, 5,8,8alpha,9-, with CAS registry number 4354-76-1, belongs to the following product categories: Anti-viral Compounds; Anti-virals; Inhibitors; Intermediates & Fine Chemicals; Non-nucleoside Reverse Transcriptase; Pharmaceuticals. It has the systematic name of (5R,5alphaR,8alphaR,9R)-9-hydroxy-5-(3,4,5-trimethoxyphenyl)-5,8,8alpha,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5alphaH)-one. This chemical is a kind of white crystalline powder. And it should be stored at the temperature of 2-8°C. This chemical is mainly used as a potent inhibitor of microtubule assembly.

Physical properties of Furo(3',4':6,7)naphtho(2,3-d)-1,3-dioxol-6(5alphaH)-one, 5,8,8a,9-: (1)ACD/LogP: 2.35; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.345; (4)ACD/LogD (pH 7.4): 2.345; (5)ACD/BCF (pH 5.5): 35.633; (6)ACD/BCF (pH 7.4): 35.633; (7)ACD/KOC (pH 5.5): 449.188; (8)ACD/KOC (pH 7.4): 449.188; (9)#H bond acceptors: 8; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 5; (12)Index of Refraction: 1.606; (13)Molar Refractivity: 104.282 cm³; (14)Molar Volume: 302.394 cm³; (15)Surface Tension: 52.765 dyne/cm; (16)Density: 1.37 g/cm³; (17)Flash Point: 210.181 °C; (18)Enthalpy of Vaporization: 93.645 kJ/mol; (19)Boiling Point: 597.92 °C at 760 mmHg; (20)Vapour Pressure: 0 mmHg at 25°C.

When you are using this chemical, please be cautious about it as the following:
This chemical is irritates to eyes, respiratory system and skin. It is harmful in contact with skin. And it is toxic by inhalation, in contact with skin and if swallowed. When use it, you must wear suitable protective clothing, gloves and eye/face protection. If contact with eyes, you should rinse immediately with plenty of water and seek medical advice. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)

You can still convert the following datas into molecular structure:
(1)SMILES: COc1cc(cc(c1OC)OC)[C@@H]2c3cc4c(cc3[C@@H]([C@@H]5[C@@H]2C(=O)OC5)O)OCO4
(2)InChI: InChI=1/C22H22O8/c1-25-16-4-10(5-17(26-2)21(16)27-3)18-11-6-14-15(30-9-29-14)7-12(11)20(23)13-8-28-22(24)19(13)18/h4-7,13,18-20,23H,8-9H2,1-3H3/t13-,18+,19-,20-/m0/s1
(3)InChIKey: YJGVMLPVUAXIQN-XVVDYKMHBO
(4)Std. InChI: InChI=1S/C22H22O8/c1-25-16-4-10(5-17(26-2)21(16)27-3)18-11-6-14-15(30-9-29-14)7-12(11)20(23)13-8-28-22(24)19(13)18/h4-7,13,18-20,23H,8-9H2,1-3H3/t13-,18+,19-,20-/m0/s1
(5)Std. InChIKey: YJGVMLPVUAXIQN-XVVDYKMHSA-N

Product Name

(5R,5aR,8aR,9R)-5,8,8a,9-Tetrahydro-9-hydroxy-5-(3,4,5-trimethoxyphenyl)-furo(3',4':6,7)naphtho[2,3-d]-1,3-dioxol-6(5aH)-one

Synthetic route

Podophyllotoxin Specification

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