467-55-0

Basic information

• Product Name: Hecogenin
• Synonyms: HECOGENIN;5-ALPHA, 20-ALPHA, 22-ALPHA, 25D-SPIROSTAN-3-BETA-OL-12-ONE;5ALPHA-SPIROSTAN-3BETA-OL-12-ONE;3BETA-HYDROXY-5ALPHA-SPIROSTAN-12-ONE;25R,5ALPHA-SPIROSTAN-3BETA-OL-12-ONE;(25R)-5-Spirostan-3-ol-12-one;Hecoginin;HECOGENIN 98.0% BY HPLC
• CAS NO: 467-55-0
• Molecular Formula: C27H42O4
• Molecular Weight: 430.62
• EINECS: 207-392-4
• Product Categories: Steroids;Biochemistry;Steroids (Others);467-55-0
• Mol File: 467-55-0.mol
• Article Data: 23

Chemical Properties

• Melting Point: 268°C
• Boiling Point: 464.85°C (rough estimate)
• Flash Point: 177.8 °C
• Appearance: /
• Density: 1.0040 (rough estimate)
• Vapor Pressure: 2.45E-14mmHg at 25°C
• Refractive Index: 1.4840 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 15.10±0.70(Predicted)
• Merck: 14,4622
• CAS DataBase Reference: Hecogenin(CAS DataBase Reference)
• NIST Chemistry Reference: Hecogenin(467-55-0)
• EPA Substance Registry System: Hecogenin(467-55-0)

Safety Data

• Hazardous Substances Data: 467-55-0(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 467-55-0 differently. You can refer to the following data:
1. antiinflammatory
2. Hecogenin, is a sapogenin present in the leaves of species from the Agave genus, possessing wide spectrum of pharmacology activities, such as having antinociceptive properties.

Purification Methods

The saponin (~35 mg) in EtOAc is chromatographed on Al2O3 and eluted with *C6H6/Et2O, and the residue on evaporation is recrystallised from Me2CO. [Mazur et al. J Am Chem Soc 82 5889 1960, Marker et al. J Am Chem Soc 69 2167 1947, Beilstein 19 III/IV 2581.]

InChI:InChI=1/C27H42O4/c1-15-7-10-27(30-14-15)16(2)24-22(31-27)12-21-19-6-5-17-11-18(28)8-9-25(17,3)20(19)13-23(29)26(21,24)4/h15-22,24,28H,5-14H2,1-4H3/t15?,16-,17-,18-,19+,20-,21-,22-,24-,25-,26+,27?/m0/s1

Synthetic route

hecogenin acetate (915-35-5) → hecogenin (467-55-0)

Conditions	Yield
With methanol; potassium hydroxide In dichloromethane at 20℃; for 18h;	99%
With methanol; potassium carbonate In tetrahydrofuran for 24h;	97%
With potassium carbonate In tetrahydrofuran; methanol at 20℃; for 12h; Inert atmosphere;	95%

(2aS,4S,5'R,6aS,6bS,8aS,8bR,9S,10R,11aS,12aS,12bR)-5',6a,8a,9-tetramethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)icosahydrospiro[naphtho[2',1':4,5]indeno[2,1-b]furan-10,2'-pyran]-8(2H)-one → hecogenin (467-55-0)

Conditions	Yield
With sodium perborate tetrahydrate In tetrahydrofuran; water for 3h;	79%

α-D-glucopyranosyl(1->4)α-D-glucopyranosyl(1->4)α-D-glucopyranosyl(1->3)hecogenin → hecogenin (467-55-0)

Conditions	Yield
With sulfuric acid	44.8%

12-methylenetigogenin (108747-55-3) → hecogenin (467-55-0)

Conditions	Yield
With sodium periodate; potassium carbonate; tert-butyl alcohol Reagens 4: Kaliumpermanganat;

3-oxo-5α-hecogenin (2137-20-4) → hecogenin (467-55-0)

Conditions	Yield
With pyridine; sodium borate
With tetrahydrofuran; lithium aluminium tetrahydride; diethyl ether Behandeln des erhaltenen Reaktionsprodukts in Pyridin mit Bernsteinsaeure-anhydrid und mit Chrom(VI)-oxid und wss. Essigsaeure, danach mit methanol. Kalilauge;
Aspergillus niger;

3β-acetoxy-(25R)-5α-spirostan-12-one (4948-48-5) → hecogenin (467-55-0)

Conditions	Yield
With hydrogenchloride; ethanol

(25R)-12α-(Aminomethyl)-5α-spirostan-3β,12β-diol (78179-47-2) → (25R)-3β-Hydroxy-C-homo-5α-spirostan-12-on (72166-67-7) + (25R)-3β-Hydroxy-C-homo-5α-spirostan-12-on (72166-68-8) + (25R)-12α-(Azidomethyl)-5α-spirostan-3β,12β-diol + hecogenin (467-55-0)

Conditions	Yield
With sodium azide; sodium nitrite Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;

3-O-<<β-D-glucopyranosyl(1->3)-β-D-glucopyranosyl(1->2> <β-D-xylopyranosyl(1->4)>-β-D-galactopyranosyl>-(25R)-5α-spirostan-12-one-3β-ol → hecogenin (467-55-0)

Conditions	Yield
With hydrogenchloride In ethanol at 100℃; for 3.5h;

3-O-<<β-D-glucopyranosyl(1->3)-β-D-glucopyranosyl(1->2> <β-D-xylopyranosyl(1->4)>-β-D-galactopyranosyl>-(25R)-5α-spirostan-12-one-3β-ol → C39H62O14 + C45H72O19 + hecogenin (467-55-0)

Conditions	Yield
With hydrogenchloride In butan-1-ol at 70℃; for 2.5h;	A 13.5 mg B 16.5 mg C 15 mg

3-O-<<β-D-xylopyranosyl(1->4)-β-D-glucopyranosyl(1->3)-β-D-glucopyranosyl(1->2> <β-D-xylopyranosyl(1->4)>-β-D-galactopyranosyl>-(25R)-5α-spirostan-12-one-3β-ol → hecogenin (467-55-0)

Conditions	Yield
With hydrogenchloride In ethanol at 100℃; for 3.5h;
Multi-step reaction with 2 steps 1: 20 mg / 1M HCl / butan-1-ol / 2.5 h / 70 °C 2: 2M HCl / ethanol / 3.5 h / 100 °C View Scheme
Multi-step reaction with 2 steps 1: 20 mg / 1M HCl / butan-1-ol / 2.5 h / 70 °C 2: 15 mg / 1M HCl / butan-1-ol / 2.5 h / 70 °C View Scheme

3-O-<<β-D-xylopyranosyl(1->4)-β-D-glucopyranosyl(1->3)-β-D-glucopyranosyl(1->2> <β-D-xylopyranosyl(1->4)>-β-D-galactopyranosyl>-(25R)-5α-spirostan-12-one-3β-ol → C39H62O14 + C45H72O19 + 3-O-<<β-D-glucopyranosyl(1->3)-β-D-glucopyranosyl(1->2> <β-D-xylopyranosyl(1->4)>-β-D-galactopyranosyl>-(25R)-5α-spirostan-12-one-3β-ol + hecogenin (467-55-0)

Conditions	Yield
With hydrogenchloride In butan-1-ol at 70℃; for 2.5h;	A 10 mg B 13.5 mg C 20 mg D 10 mg

25(R)-5α-spirostan-3β-ol-12-one 3-O-β-D-glucopyranosyl-(1->2)-[β-D-xylopyranosyl-(1->3)]-O-β-D-glucopyranosyl-(1->4)-β-D-galactopyranoside (168960-81-4) → hecogenin (467-55-0)

Conditions	Yield
With hydrogenchloride In 1,4-dioxane; water for 2h; Heating;	4.9 mg

(25R)-3β-[(O-β-D-glucopyranosyl-(1->3)-O-β-D-glucopyranosyl-(1->2)-O-[O-α-L-rhamnopyranosyl-(1->4)-β-D-glucopyranosyl-(1->3)]-O-β-D-glucopyranosyl-(1->4)-β-D-galactopyranosyl)oxy]-5α-spirostan-12-one → D-Glucose (2280-44-6) + D-Galactose (10257-28-0) + L-rhamnose (73-34-7) + hecogenin (467-55-0)

Conditions	Yield
With hydrogenchloride In 1,4-dioxane at 100℃; for 3h; Product distribution; Hydrolysis;	A 20.8 mg B 8.1 mg C 5.8 mg D 11.8 mg

hydrogenchloride (7647-01-0) + 20-isohecogenin (107492-88-6) → hecogenin (467-55-0)

hydrogenchloride (7647-01-0) + 3β-acetoxy-(25R)-5α-spirostan-12-one (4948-48-5) → hecogenin (467-55-0)

cyclopseudohecogenin → hecogenin (467-55-0)

Conditions	Yield
With hydrogenchloride; methanol

hydrogenchloride (7647-01-0) + (25R)-3β-hydroxy-5α-spirostan-12-one-(2,4-dinitro-phenylhydrazone) (17990-60-2) + tin (II)-chloride → hecogenin (467-55-0)

(25R)-3β-[{O-β-D-xylopyranosyl-(1->3)-O-β-D-glucopyranosyl-(1->2)-O-[β-D-xylopyranosyl-(1->3)]-O-β-D-glucopyranosyl-(1->4)-β-D-galactopyranosyl}oxy]-5α-spirostan-12-one → hecogenin (467-55-0)

Conditions	Yield
With hydrogenchloride In 1,4-dioxane at 98℃; for 2h;	3.4 mg

(25R)-3β-hydroxy-5α-spirostan-12-one-3-O-β-xylopyranosyl(1->4)-[α-arabinopyranosyl(1->6)]-β-glucopyranoside → hecogenin (467-55-0)

Conditions	Yield
In ethanol; sulfuric acid at 100℃; for 6h;	2 mg

(25R)-12-ethylenedioxy-5α-spirostan-3β-ol (38673-31-3) → hecogenin (467-55-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: Jones' reagent 2: Aspergillus niger View Scheme

C31H48O6 → hecogenin (467-55-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: aq. KOH 2: Jones' reagent 3: Aspergillus niger View Scheme

25R-spirost-4-ene-3,12-dione (6875-60-1) → hecogenin (467-55-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: palladium/charcoal; dioxane; methanol. KOH-solution 2: sodium borate; pyridine View Scheme

(23Ξ,25R)-23-bromo-spirost-4-ene-3,12-dione → hecogenin (467-55-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: ethanol; acetic acid; zinc-powder 2: palladium/charcoal; dioxane; methanol. KOH-solution 3: sodium borate; pyridine View Scheme

(23Ξ,25R)-2α,4α,23-tribromo-5α-spirostan-3,12-dione → hecogenin (467-55-0)

Conditions	Yield
Multi-step reaction with 4 steps 1: sodium iodide; acetone / Behandeln des Reaktionsprodukts in Aceton und Dioxan mit Chrom(II)-chlorid in wss. Salzsaeure 2: ethanol; acetic acid; zinc-powder 3: palladium/charcoal; dioxane; methanol. KOH-solution 4: sodium borate; pyridine View Scheme

(25S)-hecogenin (467-55-0, 509-99-9, 545-78-8, 38676-82-3, 72203-53-3, 107492-88-6, 119008-59-2) → hecogenin (467-55-0)

Conditions	Yield
Multi-step reaction with 2 steps 2: ethanol; aqueous hydrochloric acid View Scheme

(25R)-2α,3α-epoxy-5α-spirostan-12-one (28180-63-4) → hecogenin (467-55-0)

Conditions

Yield

Multi-step reaction with 2 steps 1: benzene; diethyl ether; lithium alanate / Behandeln einer Loesung des Reaktionsprodukts in Essigsaeure mit Chrom(VI)-oxid und wss. Essigsaeure 2: tetrahydrofuran; lithium alanate; diethyl ether / Behandeln des erhaltenen Reaktionsprodukts in Pyridin mit Bernsteinsaeure-anhydrid und mit Chrom(VI)-oxid und wss. Essigsaeure, danach mit methanol. Kalilauge View Scheme

(25R)-3β-[(O-β-D-glucopyranosyl-(1->2)-O-[β-D-glucopyranosyl-(1->3)]-O-β-D-glucopyranosyl-(1->4)-β-D-galactopyranosyl)oxy]-5α-spirostan-12-one (1174898-06-6) → hecogenin (467-55-0)

Conditions	Yield
With hydrogenchloride; water In 1,4-dioxane at 95℃; for 2h; Inert atmosphere;	1.2 mg

(25R)-3β-[(O-α-L-arabinopyranosyl-(1 → 2)-O-[β-D-xylopyranosyl-(1 → 3)]-O-β-D-glucopyranosyl-(1 → 4)-O-[α-L-rhamnopyranosyl-(1 → 2)]-β-D-galactopyranosyl)oxy]-5α-spirostan-12-one (1499187-81-3) → D-xylose (58-86-6) + L-arabinose (5328-37-0) + L-Rhamnose (3615-41-6) + D-glucose (50-99-7) + D-Galactose (59-23-4) + hecogenin (467-55-0)

Conditions	Yield
With naringinase; potassium acetate; acetic acid In aq. buffer at 20℃; for 49h; pH=4.3; Enzymatic reaction;	A n/a B n/a C n/a D n/a E n/a F 3.1 mg

O-((2aS,4S,5'R,6aS,6bS,8aS,8bR,9S,10R,11aS,12aS,12bR)-5',6a,8a,9-tetramethyl-8-oxodocosahydrospiro[naphtho[2',1':4,5]indeno[2,1-b]furan-10,2'-pyran]-4-yl)-1H-imidazole-1-carbothioate → hecogenin (467-55-0)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 2,2'-azobis(isobutyronitrile); tris-(trimethylsilyl)silane / N,N-dimethyl acetamide; 1,4-dioxane / 48 h / Inert atmosphere; Schlenk technique; Irradiation 1.2: 2 h / Inert atmosphere; Schlenk technique; Irradiation 2.1: sodium perborate tetrahydrate / tetrahydrofuran; water / 3 h View Scheme

hecogenin (467-55-0) → 3-oxo-5α-hecogenin (2137-20-4)

Conditions	Yield
With Jones reagent In acetone at 20℃; for 0.333333h;	99%
Multi-step reaction with 4 steps 1: pyridine / Ambient temperature 2: BF3-Et2O / CH2Cl2 / Ambient temperature 3: aq. KOH 4: Jones' reagent View Scheme
With pyridinium chlorochromate In dichloromethane at 0 - 20℃; for 3h;

acetic anhydride (108-24-7) + hecogenin (467-55-0) → hecogenin acetate (915-35-5)

Conditions	Yield
With pyridine at 20℃;	95%

hecogenin (467-55-0) → 3β,12β-dihydroxy-(25R)-5α-spirostane (545-77-7, 16653-52-4, 38673-26-6, 90375-72-7, 90457-38-8, 107297-25-6)

Conditions	Yield
With ammonia; lithium In tetrahydrofuran at -78 - -33℃; for 5h; Reduction;	95%
With diethyl ether; acetic acid; platinum Hydrogenation;
Stage #1: hecogenin With sodium tetrahydroborate In tetrahydrofuran; methanol at 0℃; for 2h; Stage #2: With hydrogenchloride In tetrahydrofuran; methanol; water stereoselective reaction;

p-toluenesulfonyl chloride (98-59-9) + hecogenin (467-55-0) → (25R)-12-oxo-5α-spirostan-3β-yl tosylate (60433-68-3)

Conditions	Yield
With pyridine In dichloromethane at 4℃; for 24h;	94%
With pyridine at 20℃;	93%
With pyridine
With pyridine

1,2-bis(tert-butyldimethylsilyl)hydrazine (10000-20-1) + hecogenin (467-55-0) → C39H72N2O3Si2 (690275-05-9)

Conditions	Yield
With scandium tris(trifluoromethanesulfonate) In chloroform at 55℃; for 20h;	93%

2,3,4,6-tetra-O-benzoyl-D-glucopyranosyl trichloroacetimidate (149707-75-5) + hecogenin (467-55-0) → hecogenyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside (1373440-74-4)

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate In dichloromethane at 20℃; for 1h; Inert atmosphere; Molecular sieve;	91%

acetic anhydride (108-24-7) + hecogenin (467-55-0) → (25R)-23-acetyl-22,26-epoxy-12-oxo-5α-cholesta-22-ene-3β,16β-diyl diacetate (245124-65-6)

Conditions	Yield
With boron trifluoride diethyl etherate at 20℃; for 0.833333h; Ring cleavage; acetylation;	87%
With boron trifluoride diethyl etherate at 20℃; for 0.166667h;	87%

2-O-(4-methoxybenzoyl)-3,4-di-O-triethylsilyl-β-D-xylopyranosyl-(1→3)-2-O-acetyl-4-O-triethylsilyl-α,β-L-arabinopyranosyl trichloroacetimidate (321125-08-0) + hecogenin (467-55-0) → hecogenin-3-yl 2-O-(4-methoxybenzoyl)-3,4-di-O-triethylsilyl-β-D-xylopyranosyl-(1->3)-2-O-acetyl-3-O-triethylsilyl-α-L-arabinopyranoside

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate; 4 Angstroem MS In dichloromethane at -20℃;	86%

acetic anhydride (108-24-7) + hecogenin (467-55-0) → (25R)-26-hydroxy-12,22-dioxo-5α-cholestan-3β,16β-diyl diacetate (1228298-02-9)

Conditions	Yield
Stage #1: acetic anhydride; hecogenin With boron trifluoride diethyl etherate In dichloromethane at 0℃; Stage #2: With water In dichloromethane Cooling with ice;	86%
With boron trifluoride diethyl etherate In dichloromethane at 0℃; for 0.25h;	86%
With boron trifluoride diethyl etherate In dichloromethane at 0℃; for 0.5h;

tert-butyldimethylsilyl chloride (18162-48-6) + hecogenin (467-55-0) → (25R)-3β-(tert-butyl(dimethyl)silyloxy)-5α-spirostan-12-one (909880-00-8)

Conditions	Yield
With 1H-imidazole In N,N-dimethyl-formamide for 3h;	84%

O-carboxymethylhydroxylamine hydrochloride (20295-82-3) + hecogenin (467-55-0) → (25R)-12E-[O-(carboxymethyl)oximino]-5α-spirostan-3β-ol

Conditions	Yield
With pyridine at 20℃;	84%

3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-(α/β)-D-glucopyranosyl trichloroacetimidate (146728-55-4) + hecogenin (467-55-0) → hecogenin 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (869884-28-6)

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate In dichloromethane at -20℃; for 1h; Molecular sieve;	82%

t-butyldimethylsiyl triflate (69739-34-0) + hecogenin (467-55-0) → C39H70O4Si2 (1246949-40-5)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere;	80%
With triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere;	80%

hecogenin (467-55-0) → (25R)-3α-amino-5α-spirostan-12-one (1432631-48-5)

Conditions	Yield
Stage #1: hecogenin With methanesulfonyl chloride; triethylamine In dichloromethane Stage #2: With sodium azide In dimethyl sulfoxide at 70℃; Stage #3: With 10 wt% Pd(OH)2 on carbon; hydrogen	79%
Multi-step reaction with 3 steps 1: pyridine 2: sodium azide / 60 °C 3: triphenylphosphine; water / tetrahydrofuran / 20 °C View Scheme

1,1'-Thiocarbonyldiimidazole (6160-65-2) + hecogenin (467-55-0) → O-((2aS,4S,5'R,6aS,6bS,8aS,8bR,9S,10R,11aS,12aS,12bR)-5',6a,8a,9-tetramethyl-8-oxodocosahydrospiro[naphtho[2',1':4,5]indeno[2,1-b]furan-10,2'-pyran]-4-yl)-1H-imidazole-1-carbothioate

Conditions	Yield
With dmap In dichloromethane at 55℃; for 3h;	79%

4-Phenyl-3-thiosemicarbazide (5351-69-9) + hecogenin (467-55-0) → 3β-hydroxy-5α,25R-spirostan-12-(phenyl thiosemicarbazone)

Conditions	Yield
With pyridine at 20℃;	78%
In ethanol at 20℃;

N-(2-(trifluoromethyl)phenyl)hydrazinecarbothioamide (38901-29-0) + hecogenin (467-55-0) → 3β-hydroxy-5α,25R-spirostan-12-(3'-trifluoromethylphenyl thiosemicarbazone)

Conditions	Yield
With pyridine at 20℃;	75%

4-(2-methylphenyl)-3-thiosemicarbazide (614-10-8) + hecogenin (467-55-0) → 3β-hydroxy-5α,25R-spirostan-12-(3'-methylphenyl thiosemicarbazone)

Conditions	Yield
With pyridine at 20℃;	75%

4-(2'-nitrophenyl)-3-thiosemicarbazide (73305-12-1) + hecogenin (467-55-0) → 3β-hydroxy-5α,25R-spirostan-12-(3'-nitrophenyl thiosemicarbazone)

Conditions	Yield
With pyridine at 20℃;	72%

2-furancarbonyl chloride (527-69-5) + hecogenin (467-55-0) → 3β-O-(furoyl)-5α,25R-spirostan-12-one

Conditions	Yield
Stage #1: hecogenin With pyridine; dmap; triethylamine at 20℃; for 0.333333h; Stage #2: 2-furancarbonyl chloride	71%

2-Methoxybenzoyl chloride (21615-34-9) + hecogenin (467-55-0) → 3β-O-(4'-chlorobenzoyl)-5α,25R-spirostan-12-one

Conditions	Yield
Stage #1: hecogenin With pyridine; dmap; triethylamine at 20℃; for 0.333333h; Stage #2: 2-Methoxybenzoyl chloride	70%

N-methoxylamine hydrochloride (593-56-6) + hecogenin (467-55-0) → 12-Z,E-methyloximehecogenin (1033264-82-2)

Conditions	Yield
With pyridine In toluene at 20 - 50℃;	69.5%

hecogenin (467-55-0) → (25R)-C-homo-12a-oxa-3β-hydroxy-5α-spirostan-12-one (469-13-6)

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0 - 20℃; for 120h; Baeyer-Villiger oxidation; Darkness;	69%

hecogenin (467-55-0) → (25R)-5α-spirostan-3β,12β-diol diacetate (10007-76-8)

Conditions	Yield
With sodium tetrahydroborate In 1,4-dioxane; methanol at 10℃; for 0.5h;	68%
Multi-step reaction with 2 steps 1: 95 percent / liquid NH3; Li / tetrahydrofuran / 5 h / -78 - -33 °C 2: 90 percent / NEt3; DMAP / CH2Cl2 / 5.5 h View Scheme
Multi-step reaction with 2 steps 1: NaBH4 / dioxane; methanol / 0.5 h / 10 °C 2: 8.2 g / pyridine View Scheme
Multi-step reaction with 2 steps 1: platinum; acetic acid; diethyl ether / Hydrogenation View Scheme

4-cyanobenzoyl chlorIde (6068-72-0) + hecogenin (467-55-0) → 3β-O-(5'-cyanobenzoyl)-5α,25R-spirostan-12-one

Conditions	Yield
Stage #1: hecogenin With pyridine; dmap; triethylamine at 20℃; for 0.333333h; Stage #2: 4-cyanobenzoyl chlorIde	68%

4-(2'-chlorophenyl)-3-thiosemicarbazide (42135-75-1) + hecogenin (467-55-0) → 3β-hydroxy-5α,25R-spirostan-12-(3'-chlorophenyl thiosemicarbazone)

Conditions	Yield
With pyridine at 20℃;	65%

ortho-iodophenyl chlorothionoformate + hecogenin (467-55-0) → C34H45IO5S

Conditions	Yield
With dmap In dichloromethane at 0 - 20℃;	64%

4-nitro-benzoyl chloride (122-04-3) + hecogenin (467-55-0) → 3β-O-(5'-nitrobenzoyl)-5α,25R-spirostan-12-one

Conditions	Yield
Stage #1: hecogenin With pyridine; dmap; triethylamine at 20℃; for 0.333333h; Stage #2: 4-nitro-benzoyl chloride	63%

Upstream product

• 915-35-5 hecogenin acetate 
• 133024-11-0 Chloromaloside A 
• 132998-87-9 diuranthoside B 
• 132998-89-1 Chloromaloside C 
• 137853-58-8 YS-VIII 
• 137853-58-8 YS-VII 
• 6875-60-1 25R-spirost-4-ene-3,12-dione 
• 38673-27-7 (25R)-5β-spirostan-3,12-dione 
• 1499187-81-3 (25R)-3β-[(O-α-L-arabinopyranosyl-(1 → 2)-O-[β-D-xylopyranosyl-(1 → 3)]-O-β-D-glucopyranosyl-(1 → 4)-O-[α-L-rhamnopyranosyl-(1 → 2)]-β-D-galactopyranosyl)oxy]-5α-spirostan-12-one 
• 1174898-06-6 (25R)-3β-[(O-β-D-glucopyranosyl-(1->2)-O-[β-D-glucopyranosyl-(1->3)]-O-β-D-glucopyranosyl-(1->4)-β-D-galactopyranosyl)oxy]-5α-spirostan-12-one 
• 28180-63-4 (25R)-2α,3α-epoxy-5α-spirostan-12-one 
• 467-55-0 (25S)-hecogenin 
• 38673-31-3 (25R)-12-ethylenedioxy-5α-spirostan-3β-ol 

Downstream Products

• 1266102-60-6 C₄₆H₆₄O₆ 
• 1266102-70-8 (3α,5α,11β,16β)-3,11-bis(benzyloxy)-17-bromo-16-hydroxypregnan-20-one 
• 1266102-59-3 (3α,5α,11β)-3,11-bis(benzyloxy)pregn-16-en-20-one 
• 1246949-33-6 C₄₃H₅₈O₇ 
• 1266102-57-1 C₄₂H₅₂O₇ 
• 1266102-66-2 C₄₁H₅₀O₇ 
• 1266102-48-0 C₄₁H₅₂O₆ 
• 1266102-47-9 C₄₁H₅₂O₆ 

Relevant articles and documents

Steroidal saponins from the underground parts of Hosta longipes and their inhibitory activity on tumor promoter-induced phospholipid metabolism

Phytochemical study on the underground parts of Hosta longipes gave six new steroidal saponins together with a known one. The structures of the new compounds were determined by detailed analysis of their 1H- and 13C-NMR spectra including two-dimensional NMR spectroscopy, acid-catalyzed hydrolysis followed by chemical correlation, and by comparison with spectral data of known compounds. The isolated saponins and their aglycones were examined for inhibitory activity on 12-O-tetradecanoylphorbol-13-acetate (TPA)-stimulated 32P-incorporation into phospholipids of HeLa cells to identify new antitumor-promoter compounds.

SPIROSTANOL GLYCOSIDES FROM AGAVE CANTALA

Two spirostanol glycosides, cantalasaponins -2 and -4 were isolated from the methanolic extract of the rhizomes of Agave cantala and were characterized.The first glycoside was found to be lethal against Biomphalaria glabrata, tha snail vector of the disease schistosomiasis, at a concentration of 7 ppm. Key Word Index - Agave cantala; Agavaceae; saponins; spirostanol glycosides; schistosomiasis; Biomphalaria glabrata.

Deoxygenative Borylation of Secondary and Tertiary Alcohols

Two different approaches for the deoxygenative radical borylation of secondary and tertiary alcohols are presented. These transformations either proceed through a metal-free silyl-radical-mediated pathway or utilize visible-light photoredox catalysis. Readily available xanthates or methyl oxalates are used as radical precursors. The reactions show broad substrate scope and high functional-group tolerance, and are conducted under mild and practical conditions.

Synthetic pathway to 22,23-dioxocholestanic chain derivatives and their usefulness for obtaining brassinosteroid analogues

Recognizing the functionality of the pentacyclic steroidal derivative 7a as important synthon to obtain new brassinosteroid analogs, we have accomplished the derivatization of hecogenin, a sapogenin from the 25R serie containing a carbonyl group at C-12, to a 22,23-dioxocholestanic chain derivative. Starting from hecogenin acetate (5a) or hecogenin tosylate (5b), we obtained two pentacyclic derivatives (7a and 7b) which were subjected to an oxidation reaction on the double bond at C-12(23) to obtain a 22,23- dioxocholestanic chain, with the regeneration of the carbonyl group at C-12. Reduction of the carbonyl groups lead to the 20-epi-12,23-dihydroxy-22-oxo system 11a-b. The absolute configuration of compound 11a was established by X-ray diffraction analysis.