143-62-4

Basic information

• Product Name: DIGITOXIGENIN
• Synonyms: 5BETA,20[22]-CARDENOLIDE-3BETA,14-DIOL;3BETA,14-DIHYDROXY-5BETA,20[22]-CARDENOLIDE;20(22),5BETA-CARDENOLID-3BETA,14BETA-DIOL;3,14,21-TRIHYDROXY-20(22)-NORCHOLENIC ACID LACTONE;DIGITOXIGENIN;THEVETIGENIN;3,14-dihydroxy-,(3-beta,5-beta)-card-20(22)-enolid;3-beta,14-dihydroxy-5-beta-card-20(22)-enolid
• CAS NO: 143-62-4
• Molecular Formula: C₂₃H₃₄O₄
• Molecular Weight: 374.51
• EINECS: 205-603-4
• Product Categories: Biochemistry;Steroids;Steroids (Others);ATPase
• Mol File: 143-62-4.mol
• Article Data: 28

Chemical Properties

• Melting Point: 253-255 °C (dec.)(lit.)
• Boiling Point: 423.5°C (rough estimate)
• Flash Point: 188.1°C
• Appearance: /
• Density: 1.0284 (rough estimate)
• Vapor Pressure: 2.36E-14mmHg at 25°C
• Refractive Index: 1.4433 (estimate)
• PKA: 14.93±0.70(Predicted)
• Water Solubility: 11.24mg/L(30 oC)
• Merck: 14,3162
• BRN: 95448
• CAS DataBase Reference: DIGITOXIGENIN(CAS DataBase Reference)
• NIST Chemistry Reference: DIGITOXIGENIN(143-62-4)
• EPA Substance Registry System: DIGITOXIGENIN(143-62-4)

Safety Data

• Hazard Codes: T
• Statements: 25
• Safety Statements: 45
• RIDADR: UN 3462 6.1/PG 2
• WGK Germany: 3
• RTECS: FH4975000
• HazardClass: 6.1(a)
• PackingGroup: II
• Hazardous Substances Data: 143-62-4(Hazardous Substances Data)

Usage

Uses

Cardiotonic;Na+ K+ ATPase inhibitor

Purification Methods

Dissolve digitoxigenin in EtOAc, wash it with H2O, dry it (Na2SO4), evaporate and recrystallise it from 40% aqueous EtOH or aqueous MeOH then EtOAc/Et2O. The UV has max at 218nm ( 14,500 M-1cm-1). The 3-acetate crystallises from Me2CO/Et2O with m 222-227o, [] D 20 +21o (c 1, CHCl3). [Wyss et al. Helv Chim Acta 43 644 1960, Cruz et al. J Org Chem 4 2 3580 1977, Beilstein 18 IV 1468.]

InChI:InChI=1/C23H34O4/c1-21-8-5-16(24)12-15(21)3-4-19-18(21)6-9-22(2)17(7-10-23(19,22)26)14-11-20(25)27-13-14/h11,15-19,24,26H,3-10,12-13H2,1-2H3/t15-,16+,17-,18+,19-,21+,22-,23+/m1/s1

Synthetic route

4-[(3S,5R,8R,9S,10S,13R,14S,17R)-3-(tert-Butyl-dimethyl-silanyloxy)-14-hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-5H-furan-2-one (182573-64-4) → (+)-digitoxigenin (143-62-4)

Conditions	Yield
With toluene-4-sulfonic acid In methanol for 24h; Ambient temperature;	97%
With sulfuric acid In methanol; water for 1h; Heating;	95%

digitoxin (71-63-6) → (+)-digitoxigenin (143-62-4)

Conditions	Yield
With sulfuric acid In methanol at 0℃; for 5h;	95%
With toluene-4-sulfonic acid In methanol at 20℃;	79%
With hydrogenchloride; ethanol; water

14-hydroxy-3β-tetrahydropyranyloxy-5β-card-20(22)-enolide (809-98-3) → (+)-digitoxigenin (143-62-4)

Conditions	Yield
With pyridinium p-toluenesulfonate In ethanol at 60℃; for 1h;	85%

(Digitoxigenin-3-yl)-4-O-acetyl-2,3,6-tridesoxy-α-L-erythro-hex-2-enopyranosid (29742-88-9, 33156-31-9, 99780-82-2) → (+)-digitoxigenin (143-62-4)

Conditions	Yield
With hydrogen; palladium on activated charcoal In ethanol for 2h; Product distribution;	69%

3β,14-dihydroxy-17β-(furan-3-yl)-5β,14β-androstane (1919-02-4) → (+)-digitoxigenin (143-62-4)

Conditions	Yield
Stage #1: 3β,14-dihydroxy-17β-(furan-3-yl)-5β,14β-androstane With oxygen; rose bengal; N-ethyl-N,N-diisopropylamine In dichloromethane at -78℃; Irradiation; Stage #2: With sodium tetrahydroborate; water In dichloromethane at 20℃; Further stages.;	61%

3β-O-(β-D-digitalosyl)-14-hydroxy-5β,14β-card-20(22)-enolide (18810-25-8) → 14-dehydrodigitoxigenin 3-O-β-D-digitaloside (14364-82-0) + 3β-hydroxy-5β-carda-14,20(22)-dienolide (4321-20-4) + (+)-digitoxigenin (143-62-4)

Conditions	Yield
at 245℃; other temp., other substrates;	A 4% B 2% C 6%

3β-O-(β-D-diginosyl)-14-hydroxy-5β,14β-card-20(22)-enolide (12738-19-1, 31087-87-3, 31087-88-4, 58407-69-5, 59284-73-0, 59284-75-2, 69461-00-3, 12708-27-9) → (+)-digitoxigenin (143-62-4)

Conditions	Yield
With methanol; sulfuric acid; water

3β-O-(β-D-digitalosyl)-14-hydroxy-5β,14β-card-20(22)-enolide (18810-25-8) → 14-dehydrodigitoxigenin 3-O-β-D-digitaloside (14364-82-0) + 6-deoxy-3-O-methyl-D-galactopyranose (484-37-7, 523-75-1, 25672-81-5, 78185-80-5, 78185-81-6, 118333-77-0, 484-36-6) + 3β-hydroxy-5β-carda-14,20(22)-dienolide (4321-20-4) + (+)-digitoxigenin (143-62-4)

Conditions	Yield
With water In 1,4-dioxane at 140℃; for 8h;	A 17 mg B 11 mg C 8 mg D 23 mg
With water In 1,4-dioxane at 140℃; for 8h; other cardenolide and flavonoid glycosides;	A 17 mg B 11 mg C 8 mg D 23 mg

digitoxin (71-63-6, 11054-89-0, 23394-08-3) → (+)-digitoxigenin (143-62-4)

Conditions	Yield
With sulfuric acid In methanol at 20℃; for 4h;	4 g

Digitoxigenin-3β-O-α-L-arabinofuranosid (78614-49-0, 99604-84-9, 105761-94-2, 119323-62-5) → L-arabinose (5328-37-0) + (+)-digitoxigenin (143-62-4)

Conditions	Yield
With phosphate buffer In water; dimethyl sulfoxide at 37℃; for 0.5h; 1 IE α-L-arabinofuranosidase (Aspergillus niger K 1), enzymatic cleavage;

digitoxin (71-63-6) → digitoxigen O-[2',6'-dideoxy-β-D-ribo-hexopyranosyl]-(1->4)-(2,6-dideoxy-β-D-ribo-hexopyranoside) (16479-50-8) + evatromonoside (18404-43-8) + (+)-digitoxigenin (143-62-4)

Conditions	Yield
In propan-1-ol at 125℃; for 1.16667h;
at 275℃;
at 275℃;

digitoxin (71-63-6) → digitoxigen O-[2',6'-dideoxy-β-D-ribo-hexopyranosyl]-(1->4)-(2,6-dideoxy-β-D-ribo-hexopyranoside) (16479-50-8) + β-D-digitoxopyranose (2053-00-1, 17050-70-3, 22899-74-7, 25029-50-9, 45742-39-0, 45742-40-3, 49871-87-6, 51020-42-9, 62413-93-8, 71328-50-2, 74112-04-2, 74112-05-3, 74112-09-7, 74112-10-0, 74112-11-1, 74112-14-4, 78185-01-0, 78185-02-1, 89253-95-2, 89253-96-3, 89253-97-4, 97276-35-2, 102850-49-7, 102850-50-0, 110043-58-8, 138458-66-9, 138458-67-0, 139630-51-6, 139683-22-0) + evatromonoside (18404-43-8) + (+)-digitoxigenin (143-62-4)

Conditions	Yield
With water In 1,4-dioxane at 100℃; for 35h; Further byproducts given;	A 41 mg B n/a C 33 mg D 80 mg

digitoxin (71-63-6) → digitoxigen O-[2',6'-dideoxy-β-D-ribo-hexopyranosyl]-(1->4)-(2,6-dideoxy-β-D-ribo-hexopyranoside) (16479-50-8) + β-D-digitoxosyl-(1<*>4)-β-D-digitoxose (90762-99-5, 90763-00-1, 90763-10-3, 90790-04-8) + evatromonoside (18404-43-8) + (+)-digitoxigenin (143-62-4)

Conditions	Yield
With water In 1,4-dioxane at 100℃; for 35h; Further byproducts given;	A 41 mg B n/a C 33 mg D 80 mg

14-hydroxy-3β-(tetra-O-acetyl-lin-tri[1β=>4]-D-ribo-2,6-dideoxy-hexopyranosyloxy)-5β,14β-card-20(22)-enolide (13238-31-8) → 3β-hydroxy-5β-carda-14,20(22)-dienolide (4321-20-4) + (+)-digitoxigenin (143-62-4)

Conditions	Yield
With hydrogenchloride In methanol at 50℃; for 0.5h; Mechanism;	A n/a B 15 mg

3β,14β,21-trihydroxy-5β-pregnane-20-one (3946-61-0) + malonyl coenzyme A → (+)-digitoxigenin (143-62-4)

Conditions	Yield
With 21-hydroxy-malonyltransferase enzyme; Hepes-KOH buffer In dimethyl sulfoxide at 90℃; for 1h;

hydrogenchloride (7647-01-0) + digitoxin (71-63-6) → (+)-digitoxigenin (143-62-4)

Conditions	Yield
at 30℃; Rate constant; Hydrolysis;

digilanide-A → (+)-digitoxigenin (143-62-4)

Conditions	Yield
With ethanol; sulfuric acid; water

evomonoside → (+)-digitoxigenin (143-62-4)

Conditions	Yield
With hydrogenchloride; water; acetone

purpureaglucoside-A → (+)-digitoxigenin (143-62-4)

Conditions	Yield
With hydrogenchloride; ethanol; water

digitoxigen (β-D-glucopyranosyl)-(1→4)-(2,6-dideoxy-β-D-ribohexopyranosyl)-(1→4)-(2,6-dideoxy-β-D-ribohexopyranosyl)-(1→4)-2,6-dideoxy-β-D-ribohexopyranoside (19855-40-4) + aqueous methanol. sulfuric acid → D-digitxose (527-52-6) + (+)-digitoxigenin (143-62-4) + digilanidobiose

Digitoxigenin 3-O-bisdigitoxosideacetyldigilanidobioside, or lanatoside A (17575-20-1) + diluted aq.-ethanolic sulfuric acid → D-digitxose (527-52-6) + (+)-digitoxigenin (143-62-4) + digilanidobiose

Conditions	Yield
at 40℃; anschliessendes Behandeln mit verd. wss. Schwefelsaeure;

Digitoxigenin 3-O-bisdigitoxosideacetyldigilanidobioside, or lanatoside A (17575-20-1) + diluted aqueous methanol. hydrochloric acid → D-digitxose (527-52-6) + (+)-digitoxigenin (143-62-4) + O3-acetyl-digilanidobiose

Conditions	Yield
anschliessendes Behandeln mit verd. wss. Salzsaeure;

Digitoxigenin 3-O-bisdigitoxosideacetyldigilanidobioside, or lanatoside A (17575-20-1) → (+)-digitoxigenin (143-62-4)

Conditions	Yield
With water

C27H36OSi (932024-66-3) → (+)-digitoxigenin (143-62-4)

Conditions

Yield

Multi-step reaction with 7 steps 1.1: 63 percent / K2CO3; org. peroxide / benzene / 20 °C 2.1: t-BuLi; lithium 2-thienylcyanocuprate / diethyl ether; tetrahydrofuran / -78 - -10 °C 2.2: 91 percent / diethyl ether; tetrahydrofuran / -78 - -30 °C 3.1: 99 percent / aq. TsOH / acetone / Heating 4.1: 82 percent / Cs2CO3 / acetonitrile / Heating 5.1: DIBAL-H / CH2Cl2 / -78 °C 5.2: KH; CS2; MeI / tetrahydrofuran / 20 °C 5.3: n-Bu3SnH; AIBN / benzene / Heating 6.1: 98 percent / TBAF / tetrahydrofuran / Heating 7.1: O2; Rose bengal; DIPEA / CH2Cl2 / -78 °C / Irradiation 7.2: 61 percent / NaBH4; H2O / CH2Cl2 / 20 °C View Scheme

C41H54O5Si (932024-72-1) → (+)-digitoxigenin (143-62-4)

Conditions

Yield

Multi-step reaction with 5 steps 1.1: 99 percent / aq. TsOH / acetone / Heating 2.1: 82 percent / Cs2CO3 / acetonitrile / Heating 3.1: DIBAL-H / CH2Cl2 / -78 °C 3.2: KH; CS2; MeI / tetrahydrofuran / 20 °C 3.3: n-Bu3SnH; AIBN / benzene / Heating 4.1: 98 percent / TBAF / tetrahydrofuran / Heating 5.1: O2; Rose bengal; DIPEA / CH2Cl2 / -78 °C / Irradiation 5.2: 61 percent / NaBH4; H2O / CH2Cl2 / 20 °C View Scheme

C39H50O4Si (932024-73-2) → (+)-digitoxigenin (143-62-4)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: DIBAL-H / CH2Cl2 / -78 °C 1.2: KH; CS2; MeI / tetrahydrofuran / 20 °C 1.3: n-Bu3SnH; AIBN / benzene / Heating 2.1: 98 percent / TBAF / tetrahydrofuran / Heating 3.1: O2; Rose bengal; DIPEA / CH2Cl2 / -78 °C / Irradiation 3.2: 61 percent / NaBH4; H2O / CH2Cl2 / 20 °C View Scheme

C39H52O3Si (932024-60-7) → (+)-digitoxigenin (143-62-4)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 98 percent / TBAF / tetrahydrofuran / Heating 2.1: O2; Rose bengal; DIPEA / CH2Cl2 / -78 °C / Irradiation 2.2: 61 percent / NaBH4; H2O / CH2Cl2 / 20 °C View Scheme

C39H50O4Si (932024-61-8) → (+)-digitoxigenin (143-62-4)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: 82 percent / Cs2CO3 / acetonitrile / Heating 2.1: DIBAL-H / CH2Cl2 / -78 °C 2.2: KH; CS2; MeI / tetrahydrofuran / 20 °C 2.3: n-Bu3SnH; AIBN / benzene / Heating 3.1: 98 percent / TBAF / tetrahydrofuran / Heating 4.1: O2; Rose bengal; DIPEA / CH2Cl2 / -78 °C / Irradiation 4.2: 61 percent / NaBH4; H2O / CH2Cl2 / 20 °C View Scheme

C27H34O2Si (932024-62-9) → (+)-digitoxigenin (143-62-4)

Conditions

Yield

Multi-step reaction with 6 steps 1.1: t-BuLi; lithium 2-thienylcyanocuprate / diethyl ether; tetrahydrofuran / -78 - -10 °C 1.2: 91 percent / diethyl ether; tetrahydrofuran / -78 - -30 °C 2.1: 99 percent / aq. TsOH / acetone / Heating 3.1: 82 percent / Cs2CO3 / acetonitrile / Heating 4.1: DIBAL-H / CH2Cl2 / -78 °C 4.2: KH; CS2; MeI / tetrahydrofuran / 20 °C 4.3: n-Bu3SnH; AIBN / benzene / Heating 5.1: 98 percent / TBAF / tetrahydrofuran / Heating 6.1: O2; Rose bengal; DIPEA / CH2Cl2 / -78 °C / Irradiation 6.2: 61 percent / NaBH4; H2O / CH2Cl2 / 20 °C View Scheme

acetic anhydride (108-24-7) + (+)-digitoxigenin (143-62-4) → digitoxigenin 3-acetate (808-19-5)

Conditions	Yield
With pyridine; dmap at 20 - 30℃; Inert atmosphere;	100%
In pyridine at 24℃; for 28h;	98%
With sodium acetate
In pyridine
With pyridine

3,4-dihydro-2H-pyran (110-87-2) + (+)-digitoxigenin (143-62-4) → 14-hydroxy-3β-tetrahydropyranyloxy-5β-card-20(22)-enolide (809-98-3)

Conditions	Yield
polymer bound diphenylphosphane hydrobromide In dichloromethane at 20℃; for 3h;	99%
With ethyl acetate; trichlorophosphate
With pyridinium p-toluenesulfonate In dichloromethane

C14H22O5 (1268341-16-7) + (+)-digitoxigenin (143-62-4) → C32H46O6 (1268341-20-3)

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); triphenylphosphine In dichloromethane; chloroform at 0℃;	98%

t-butyldimethylsiyl triflate (69739-34-0) + (+)-digitoxigenin (143-62-4) → 4-[(3S,5R,8R,9S,10S,13R,14S,17R)-3-(tert-Butyl-dimethyl-silanyloxy)-14-hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-5H-furan-2-one (182573-64-4)

Conditions	Yield
With pyridine In dichloromethane at 20℃; for 1h;	96%

C13H20O5 (1268341-15-6) + (+)-digitoxigenin (143-62-4) → C31H44O6 (1268341-19-0)

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); triphenylphosphine In dichloromethane; chloroform at 0℃;	94%

(+)-digitoxigenin (143-62-4) → digitoxigenone (1102-88-1)

Conditions	Yield
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In dimethyl sulfoxide for 3h; Ambient temperature;	92%
With N-methyl-2-indolinone; tetrapropylammonium perruthennate In dichloromethane at 20℃; Oxidation;	89%
Stage #1: (+)-digitoxigenin With chromium(VI) oxide; sulfuric acid In water; acetone at 0℃; for 0.333333h; Stage #2: In methanol; water; acetone at 0℃; for 0.333333h;	84%

C12H18O5 (1268341-13-4) + (+)-digitoxigenin (143-62-4) → C30H42O6 (1268341-17-8)

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); triphenylphosphine In dichloromethane; chloroform at 0℃;	90%

4-Nitrophenyl chloroformate (7693-46-1) + (+)-digitoxigenin (143-62-4) → 4-nitrophenyl carbamate-3-O-digitoxigenin

Conditions	Yield
With pyridine In 1,2-dichloro-ethane for 16h; Molecular sieve;	88.56%

tert-butyl ((2R,6R)-6-methyl-5-oxo-5,6-dihydro-2H-pyran-2-yl) carbonate (679412-06-7) + (+)-digitoxigenin (143-62-4) → (2R,6S)-2-methyl-6-(digitoxigenoxy)-2H-pyran-3(6H)-one (1256497-85-4)

Conditions	Yield
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; triphenylphosphine In tetrahydrofuran; dichloromethane at 0℃; for 8h; Inert atmosphere;	88%
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; triphenylphosphine In dichloromethane at 0℃; for 8h;	88%
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; triphenylphosphine In dichloromethane at 0℃; for 12h;	83%

C13H20O5 (1268341-14-5) + (+)-digitoxigenin (143-62-4) → C31H44O6 (1268341-18-9)

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); triphenylphosphine In dichloromethane; chloroform at 0℃;	88%

3,4-Di-O-acetyl-1,5-anhydro-2,6-didesoxy-D-ribo-hex-1-enit (69483-67-6) + (+)-digitoxigenin (143-62-4) → (Digitoxigenin-3-yl)-3,4-di-O-acetyl-2,6-didesoxy-2-iod-α-D-altropyranosid (83025-21-2, 99694-28-7, 99694-29-8)

Conditions	Yield
With N-iodo-succinimide In acetonitrile	86%
With N-iodo-succinimide In dichloromethane; acetonitrile for 168h;	86%

tert-butyl ((2S,6R)-6-methyl-5-oxo-5,6-dihydro-2H-pyran-2-yl) carbonate (912454-82-1) + (+)-digitoxigenin (143-62-4) → (2R,6R)-2-methyl-6-(digitoxygenoxy)-2H-pyran-3(6H)-one

Conditions	Yield
With triphenylphosphine; tris(dibenzylideneacetone)dipalladium (0) In tetrahydrofuran; dichloromethane; chloroform at 0℃; for 8h;	86%
With triphenylphosphine; tris(dibenzylideneacetone)dipalladium(0) chloroform complex In dichloromethane at 0℃; for 8h;	86%
With palladium; triphenylphosphine	86%
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; triphenylphosphine In tetrahydrofuran; dichloromethane at 0℃; for 8h; Inert atmosphere;	86%

­tert-­butyl-­5,6-­dihydro-­6-­methyl-­5-­oxo-­2H-­pyran-­2-­yl carbonate + (+)-digitoxigenin (143-62-4) → C29H40O6 (1256497-88-7)

Conditions	Yield
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; triphenylphosphine In tetrahydrofuran; dichloromethane at 0℃; for 8h; Inert atmosphere;	85%

1,5-anhydro-3,4-bis(triethylsilyl)-2,6-dideoxy-L-lyxo-hex-1-enitol (476469-65-5) + (+)-digitoxigenin (143-62-4) → 4-[(3S,5R,8R,9S,10S,13R,14S,17R)-14-Hydroxy-10,13-dimethyl-3-((2R,4S,5R,6S)-6-methyl-4,5-bis-triethylsilanyloxy-tetrahydro-pyran-2-yloxy)-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-5H-furan-2-one (476469-66-6)

Conditions	Yield
With camphor-10-sulfonic acid In dichloromethane; toluene at 20℃; for 12h;	84%

2,3,5-tri-O-acetyl-D-ribofuranosyl bromide (39110-68-4) + (+)-digitoxigenin (143-62-4) → 3-O-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)digitoxigenin (99617-50-2)

Conditions	Yield
With mercury(II) cyanide In acetonitrile at 60℃; for 2h;	83%

α/β-1-trichloroacetaimidate-2,3,4-tribenzoyl-L-ribose (1207607-99-5) + (+)-digitoxigenin (143-62-4) → C49H54O11 (1207607-91-7)

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate In dichloromethane at 0℃; for 0.333333h; Molecular sieve; Inert atmosphere;	82%

tert-butyl ((2S,6S)-6-methyl-5-oxo-5,6-dihydro-2H-pyran-2-yl) carbonate (865484-73-7) + (+)-digitoxigenin (143-62-4) → C29H40O6 (1256497-84-3)

Conditions	Yield
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; triphenylphosphine In tetrahydrofuran; dichloromethane at 0℃; for 6h; Inert atmosphere;	82%
With tris-(dibenzylideneacetone)dipalladium(0); triphenylphosphine In dichloromethane; chloroform at 0℃;	82%
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; triphenylphosphine In dichloromethane at 0℃; for 8h;	82%
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; triphenylphosphine In dichloromethane

tert-butyl ((2S,6S)-6-methyl-5-oxo-5,6-dihydro-2H-pyran-2-yl) carbonate (865484-73-7) + (+)-digitoxigenin (143-62-4) → (2S,6R)-2-methyl-6-(digitoxigenoxy)-2H-pyran-3(6H)-one

Conditions	Yield
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; triphenylphosphine In tetrahydrofuran; dichloromethane at 0℃; for 6h;	82%

4-oxo-4-(2-(trimethylsilyl)ethoxy)butanoic acid (93790-78-4) + (+)-digitoxigenin (143-62-4) → 14-hydroxy-5β,14β-card-20(22)-enolid-3β-yl 2-(trimethylsilyl)ethyl butanedioate (107938-48-7)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In benzene for 3h; Ambient temperature;	78%

(+)-digitoxigenin (143-62-4) → Menabegenin (508-88-3)

Conditions	Yield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 50℃; for 16h;	76%
With sodium acetate; sodium p-hydroxybenzenesulfonate; N,N-dimethyl-formamide at 125℃;

C46H46NO7PS (129823-37-6) + (+)-digitoxigenin (143-62-4) → (3β,5β,14β,17β)-3β-<(2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl)oxy>-14-hydroxycard-20(22)-enolide (103368-07-6, 103368-08-7) + (3β,5β,14β,17β)-3β-<(2,3,4-tri-O-benzyl-β-L-rhamnopyranosyl)oxy>-14-hydroxycard-20(22)-enolide (103368-07-6, 103368-08-7)

Conditions	Yield
With 4 A molecular sieve; boron trifluoride diethyl etherate In dichloromethane at -10℃; for 1h;	A 76% B 8%

Acetic acid (2S,3R,4S,6S)-6-[(2S,3R,4S)-4-(tert-butyl-dimethyl-silanyloxy)-2-methyl-3,4-dihydro-2H-pyran-3-yloxy]-3-((2S,4S,5R,6S)-4,5-diacetoxy-6-methyl-tetrahydro-pyran-2-yloxy)-2-methyl-tetrahydro-pyran-4-yl ester (476469-56-4) + (+)-digitoxigenin (143-62-4) → C53H84O16Si (476469-57-5)

Conditions	Yield
With camphor-10-sulfonic acid In dichloromethane; toluene at 20℃; for 10h;	75%

phenyl-β-D-glucopyranoside (1464-44-4) + (+)-digitoxigenin (143-62-4) → digitoxigenin 3-O-β-D-glucoside (17059-16-4)

Conditions	Yield
In water; acetonitrile at 10℃; for 12h; β-galactosidase (obt. from Asp. oryzae), phosphate buffer pH=5;	74.1%
With β-galactosidase In water; acetonitrile at 10℃; for 12h; phosphate buffer (pH 5);	74.1%

(+)-digitoxigenin (143-62-4) → 3β,14-dihydroxy-17β-(furan-3-yl)-5β,14β-androstane (1919-02-4)

Conditions	Yield
Stage #1: (+)-digitoxigenin With diisobutylaluminium hydride In tetrahydrofuran at -5℃; Stage #2: With manganese(IV) oxide In 1,4-dioxane; water; acetic acid	74%

(+)-digitoxigenin (143-62-4) → 3β,14-dihydroxy-17β-(furan-3-yl)-5β,14β-androstane (1919-02-4) + 24-Nor-5β,14β-chol-20(22)-en-3β,14,21,23-tetraol (116499-22-0) + 17β-(Fur-3-yl)-5β-androst-14-en-3β-yl-acetat (13957-85-2)

Conditions	Yield
With diisobutylaluminium hydride In tetrahydrofuran 1.) -30 deg C - -35 deg C, 1 h, 2.) up to 0 deg C during 30 min;	A 71% B 14.6% C 370 mg
With diisobutylaluminium hydride In tetrahydrofuran 1.) -30 deg C to -35 deg C, 1 h, 2.) up to 0 deg C during 30 min;	A 71% B 14.6% C 370 mg

4-isothiocyanato benzoyl chloride (53611-24-8) + (+)-digitoxigenin (143-62-4) → 14-hydroxy-3β-(4-isothiocyanatobenzoyloxy)-5β,14β-card-20(22)-enolide

Conditions	Yield
With dmap In pyridine at 20℃; for 3h; Esterification;	68%

Upstream product

• 12738-19-1 3β-O-(β-D-diginosyl)-14-hydroxy-5β,14β-card-20(22)-enolide 
• 71-63-6 digitoxin 
• 18810-25-8 3β-O-(β-D-digitalosyl)-14-hydroxy-5β,14β-card-20(22)-enolide 
• 71-63-6 digitoxin 
• 29742-88-9 (Digitoxigenin-3-yl)-4-O-acetyl-2,3,6-tridesoxy-α-L-erythro-hex-2-enopyranosid 
• 78614-49-0 Digitoxigenin-3β-O-α-L-arabinofuranosid 
• 809-98-3 14-hydroxy-3β-tetrahydropyranyloxy-5β-card-20(22)-enolide 
• 13238-31-8 14-hydroxy-3β-(tetra-O-acetyl-lin-tri[1β=>4]-D-ribo-2,6-dideoxy-hexopyranosyloxy)-5β,14β-card-20(22)-enolide 
• 3946-61-0 3β,14β,21-trihydroxy-5β-pregnane-20-one 
• 182573-64-4 4-[(3S,5R,8R,9S,10S,13R,14S,17R)-3-(tert-Butyl-dimethyl-silanyloxy)-14-hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-5H-furan-2-one 
• 7647-01-0 hydrogenchloride 
• 17575-20-1 Digitoxigenin 3-O-bisdigitoxosideacetyldigilanidobioside, or lanatoside A 
• 57292-22-5 digitoxigen O-[2'',6''-dideoxy-β-D-ribo-hexopyranosyl]-(1->4)-O-[3'-O-acetyl-2',6'-dideoxy-β-D-ribo-hexopyranosyl]-(1->4)-(3-O-acetyl-2,6-dideoxy-β-D-ribo-hexopyranoside 
• 17059-16-4 digitoxigenin 3-O-β-D-glucoside 

Downstream Products

• 2287-95-8 14-hydroxy-5β,14β-card-20(22)-enolid-3β-yl hydrogen butanedioate 
• 122215-18-3 3β-(2-carboxy-benzoyloxy)-14-hydroxy-5β,14β-card-20(22)-enolide 
• 808-19-5 digitoxigenin 3-acetate 
• 42716-82-5 digitoxigenin-3β-N,N-diethylglycyl ester 
• 35068-75-8 14-hydroxy-3β-(tetra-O-acetyl-β-D-glucopyranosyloxy)-5β,14β-card-20(22)-enolide 
• 3946-61-0 3β,14β,21-trihydroxy-5β-pregnane-20-one 
• 4427-85-4 3β,14β-dihydroxy-5β-20(R)-cardanolide 
• 464-82-4 (20S,21S)-14,21-epoxy-3β-hydroxy-5β,14β-cardanolide 
• 4321-20-4 3β-hydroxy-5β-carda-14,20(22)-dienolide 
• 4427-79-6 Δ¹⁴-anhydrodigitoxigenin 
• 1102-88-1 digitoxigenone 
• 1672-46-4 digoxigenin 
• 465-20-3 bufalin 
• 143-62-4 3-epidigitoxigenin 

Related news

Synthesis and biological evaluation of 2-Hydroxy derivatives of DIGITOXIGENIN (cas 143-62-4) and 3-EpiDIGITOXIGENIN (cas 143-62-4)1A preliminary account of this work has been presented at the First International Electronic Conference on Synthetic Organic Chemistry (ECSOC-1), A0012, 1–30 September 1997; http://www.mdpi.org/escoc-1.htm109/30/2019

The four stereoisomers of the 2-hydroxy derivatives of digitoxigenin and 3-epidigitoxigenin have been synthesized, their structures established by NMR, and their binding affinity for the digitalis receptor on Na+, K+-ATPase evaluated. These derivatives showed lower affinities than the parent com...detailed

Cytotoxic and cytostatic effects of DIGITOXIGENIN (cas 143-62-4) monodigitoxoside (DGX) in human lung cancer cells and its link to Na,K-ATPase09/29/2019

Cardiac glycosides (CGs) are natural compounds widely used to treat several cardiac conditions and more recently have been recognized as potential antitumor agents. They are known as Na,K-ATPases ligands, which is a promising drug target in cancer. In this study, the short and long-lasting cytot...detailed

Effect of ouabain, digoxin and DIGITOXIGENIN (cas 143-62-4) on potassium uptake and histamine release from rat peritoneal mast cells09/28/2019

Rat peritoneal mast cells were used to study the effects of digitalis glycosides on potassium uptake and histamine release induced by compound 48/80, substance P and egg-albumin (immunological release). In the absence of calcium all glycosides inhibited potassium uptake. Ouabain and digoxin enha...detailed

Relevant articles and documents

THERMAL TRANSFORMATION OF CARDIAC GLYCOSIDES II. ACIDLESS HYDROLYSIS OF LABILE GLYCOSIDES IN AQUEOUS ALCOHOLIC SOLUTIONS AND PROSPECTS FOR ITS UTILIZATION

The thermal transformations of cardiac glycosides in neutral alcoholic solutions have been investigated.The kinetics of their acidless hydrolysis at 100 and 142 deg C and the activation energy of the process have been studied.The possibility has been shown of the stepwise hydrolysis of natural trisdigitoxosides with the production of difficulty available mono- and bisdigitoxosides.The following were used as the objects of investigation: convallatoxin, glucostrophanthidin, cheirotoxin, desglucocheirotoxin, erycordin, erysimin, erysimoside, digitoxin, and cymarin.

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Digitoxigenin-3-O-β-D-glucopyranoside from the roots of Sapium sebiferum

The plant Sapium sebiferum is commonly known as Vilayati shisham in Hindi and belongs to natural order Euphorbiaceae. The plant is widely cultivated in India. The ethyl acetate soluble fraction of the concentrated ethyl alcohol soluble part of its roots when subjected to column chromatography yielded a yellow coloured compound, m.f. C29H44O9, m.p. 200-201 °C [α]D -19.3°, M+ = 536, which on various chemical degradations, colour reactions and spectral analysis was identified as digitoxigenin-3-O-β-D-glucopyranoside AC-4.

GLYCOSIDE COMPOUNDS AND PHARMACEUTICAL COMPOSITIONS THEREOF

The present invention provides glycoside compounds, methods of preparing such compounds, pharmaceutical compositions comprising such compounds, and a method for the treatment of hyperproliferative diseases using the same.