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Podophyllotoxin

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Name

Podophyllotoxin

EINECS 208-250-4
CAS No. 518-28-5 Density 1.37 g/cm3
PSA 92.68000 LogP 2.40920
Solubility N/A 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 Molecular Structure of 518-28-5 ((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) Hazard Symbols ToxicT
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;

Article Data 43

Podophyllotoxin Synthetic route

Conditions
ConditionsYield
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
ConditionsYield
With 4 A molecular sieve; zinc(II) chloride In tetrahydrofuran at 64℃; for 2.5h;85%
With molecular sieve; zinc(II) chloride In tetrahydrofuran75%
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
ConditionsYield
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
ConditionsYield
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

A

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

B

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

D

518-28-5

podofilox

Conditions
ConditionsYield
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
Conditions
ConditionsYield
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

C32H35NO8S

A

4375-07-9

epipodophyllotoxin

B

518-28-5

podofilox

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

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

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