Tigogenin supplier | CasNO.77-60-1

Name
Tigogenin
EINECS 201-041-9
CAS No. 77-60-1
Article Data71
CAS DataBase
Density 1.11 g/cm³
Solubility
Melting Point 202-204 °C
Formula C₂₇H₄₄O₃
Boiling Point 516.6 °C at 760 mmHg
Molecular Weight 416.645
Flash Point 266.2 °C
Transport Information
Appearance White, micro-cryst. powder
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 5a-Spirostan-3b-ol (7CI);5a-Spirostan-3b-ol, (25R)- (8CI);(25R)-5a-Spirostan-3b-ol;
PSA 38.69000
LogP 5.79380

Synthetic route

: 512-04-9
diosgenin

: 77-60-1
tigogenin

Conditions

Conditions	Yield
With hydrogen; palladium dihydroxide In ethanol; dichloromethane	99%
With hydrogen; acetic acid; palladium on activated charcoal In ethanol; dichloromethane at 20℃; under 760 Torr; for 12h;	93%
With 5% Pd/C; hydrogen In ethyl acetate at 20℃; under 3750.38 Torr;
With 5%-palladium/activated carbon; hydrogen In methanol at 20℃; for 3h;

: 915-35-5
hecogenin acetate

: 77-60-1
tigogenin

Conditions

Conditions	Yield
Stage #1: hecogenin acetate With hydrazine hydrate In 2-ethoxy-ethanol at 136℃; Inert atmosphere; Stage #2: With potassium hydroxide In 2-ethoxy-ethanol at 136℃; for 3h; Inert atmosphere;	98%

: 61046-18-2
(25R)-5α-Spirostan-2β,3α-diol

: 77-60-1
tigogenin

Conditions

Conditions	Yield
With palladium 10% on activated carbon; hydrogen; acetic acid under 1500.15 Torr; for 24h;	98%

: 690275-05-9
C39H72N2O3Si2

: 77-60-1
tigogenin

Conditions

Conditions	Yield
With potassium tert-butylate; tert-butyl alcohol In dimethyl sulfoxide at 100℃; for 24h;	95%

: 26-O-β-D-glucopyransoyl-(25R)-5β-furostane-3β,22ξ,26-triol 3-O-[α-L-rhamnopyranosyl (1->)]-β-D-glucopyranside

: 77-60-1
tigogenin

Conditions

Conditions	Yield
With hydrogenchloride In ethanol for 3h; Heating;	57.9%

: 67-56-1
methanol

: trigoneoside VIIIb

A: 77-60-1
tigogenin

B: 97-30-3, 617-04-9, 709-50-2, 1824-94-8, 2152-78-5, 3396-99-4, 6819-48-3, 18469-06-2, 20550-04-3, 22277-65-2, 29411-57-2, 35437-40-2, 35437-43-5, 36191-11-4, 36191-12-5, 39598-79-3, 39598-80-6, 39598-89-5, 51023-63-3, 51223-62-2, 51224-38-5, 51224-39-6, 51224-40-9, 51224-41-0, 51819-81-9, 51819-82-0, 51819-83-1, 56688-81-4, 62279-53-2, 64281-79-4, 64281-80-7, 64912-19-2, 66101-73-3, 78184-90-4, 84368-39-8, 84368-40-1, 84368-41-2, 92142-37-5, 93302-26-2, 103421-28-9, 115794-08-6, 3149-68-6
methyl D-glucopyranoside

C: 91-09-8, 612-05-5, 1825-00-9, 2500-78-9, 3867-83-2, 3945-28-6, 5328-63-2, 6206-67-3, 6207-01-8, 6207-03-0, 7404-24-2, 17289-61-1, 18449-76-8, 33509-64-7, 36793-06-3, 41897-31-8, 41897-32-9, 41897-33-0, 41897-34-1, 41897-37-4, 41897-38-5, 41897-39-6, 53448-52-5, 65137-86-2, 89615-04-3, 89615-05-4, 131233-91-5, 14703-09-4
methyl xyloside

D: 1128-40-1, 1198-82-9, 2592-55-4, 5155-43-1, 6340-52-9, 10503-91-0, 14009-07-5, 14687-15-1, 14917-55-6, 15814-59-2, 24332-98-7, 34299-65-5, 42214-00-6, 42214-11-9, 57783-34-3, 57783-36-5, 57783-38-7, 57783-40-1, 57783-42-3, 58525-46-5, 58525-47-6, 58525-48-7, 62182-01-8, 62182-02-9, 65310-00-1, 65941-62-0, 68069-80-7, 71116-57-9, 72274-54-5, 72274-55-6, 73036-22-3, 83198-64-5, 85505-15-3, 102517-74-8, 109718-80-1, 109718-81-2, 125280-09-3, 129172-95-8, 63864-94-8
methyl L-rhamnopyranoside

Conditions

Conditions	Yield
With hydrogenchloride for 2.5h; Product distribution; Heating;	A 51.5% B n/a C n/a D n/a

...Expand

: 470-07-5
tigogenone

A: 77-60-1
tigogenin

B: 6788-40-5
(25R)-5α-Spirostan-3α-ol

Conditions

Conditions	Yield
With lithium aluminium tetrahydride In diethyl ether for 3h; Ambient temperature;	A 17% B 8%

: 64-17-5
ethanol

: 108990-28-9
(25R)-22-ethoxy-5α,22αH-furostan-3β,26-diol

: 64-19-7
acetic acid

: 77-60-1
tigogenin

...Expand

: 64-17-5
ethanol

: 118633-83-3
(25R)-5α-furost-22ξ-ene-3β,26-diol

: 64-19-7
acetic acid

: 77-60-1
tigogenin

...Expand

: 118633-83-3
(25R)-5α-furost-22ξ-ene-3β,26-diol

: 77-60-1
tigogenin

Conditions

Conditions	Yield
at 150℃;

: 122386-94-1
(25R)-3β.26-dihydroxy-5α-cholestanedione-(16.22)

: 555-31-7
aluminum isopropoxide

: 67-63-0
isopropyl alcohol

: 77-60-1
tigogenin

...Expand

: 67-56-1
methanol

: C69H118O26

A: 3149-37-9, 3149-38-0, 23009-68-9, 23262-64-8, 23397-56-0, 27552-00-7, 31085-65-1, 51385-14-9
methyl 2,3,6-tri-O-methyl α-D-galactopyranoside

B: 35939-71-0
methyl 2,4,6-tri-O-methyl-α-D-glucopyranoside

C: 77-60-1
tigogenin

D: 2296-43-7, 2876-84-8, 2876-85-9, 2876-86-0, 2876-87-1, 2876-90-6, 7381-06-8, 14187-58-7, 14550-94-8, 20188-52-7, 50773-45-0, 72984-55-5, 90760-77-3
methyl 2,3,4-tri-O-methyl α,β-D-xylopyranoside

E: 82262-93-9
methyl 4,6-di-O-methyl α,β-D-glucopyranoside

Conditions

Conditions	Yield
With hydrogenchloride Product distribution; Heating;

...Expand

: C69H116O37

: 77-60-1
tigogenin

Conditions

Conditions	Yield
With sulfuric acid In water at 110℃; for 10h;

: C63H104O31

: 77-60-1
tigogenin

Conditions

Conditions	Yield
With sulfuric acid In water at 110℃; for 10h;

: diurnoside

A: 87-72-9, 608-45-7, 608-46-8, 608-47-9, 2460-44-8, 6748-95-4, 6763-34-4, 7261-26-9, 7283-06-9, 7283-07-0, 7296-55-1, 7296-56-2, 7296-58-4, 7296-59-5, 7296-60-8, 7296-61-9, 7296-62-0, 7322-30-7, 10257-31-5, 10257-32-6, 10257-33-7, 10257-34-8, 10257-35-9, 19982-83-3, 20242-88-0, 28697-53-2, 36562-42-2, 41546-41-2, 89299-64-9, 107655-34-5, 115794-06-4, 115794-07-5, 130550-15-1, 130606-21-2
D-Xylose

B: 2280-44-6
D-Glucose

C: 10257-28-0
D-Galactose

D: 77-60-1
tigogenin

Conditions

Conditions	Yield
With hydrogenchloride In methanol at 110℃; for 4h;

...Expand

: (3β,5α,25R)-spirostan-3-yl O-β-D-xylopyranosyl-(1-3)-β-D-glucopyranosyl-(1-2)-[β-D-xylopyranosyl-(1-3)]-β-D-glucopyranosyl-(1-4)-β-D-galactopyranoside

: 77-60-1
tigogenin

Conditions

Conditions	Yield
With sulfuric acid In ethanol for 2h; Heating;

: 470-07-5
tigogenone

: 77-60-1
tigogenin

Conditions

Conditions	Yield
Aspergillus niger;

: 2530-07-6
tigogenin acetate

: 77-60-1
tigogenin

Conditions

Conditions	Yield
Aspergillus niger;

: 110124-76-0
(25R)-5α-spirostan-3β-ol 3-O-

: 77-60-1
tigogenin

Conditions

Conditions	Yield
With sulfuric acid at 105℃; for 12h;

: 35959-24-1
(25R)-5α-spirostan-3β-ol 3-O-β-D-galactopyranoside

: 77-60-1
tigogenin

Conditions

Conditions	Yield
With sulfuric acid at 105℃; for 12h;

: tigogenyl α-L-rhamnopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→4)]-β-D-galactopyranoside

: 77-60-1
tigogenin

Conditions

Conditions	Yield
With hydrogenchloride In 1,4-dioxane; water at 100℃;	7.2 mg

: 64-17-5
ethanol

: 512-04-9
diosgenin

palladium/charcoal: palladium/charcoal

: 77-60-1
tigogenin

Conditions

Conditions	Yield
Hydrogenation;

...Expand

: 64-19-7
acetic acid

: 512-04-9
diosgenin

palladium/charcoal: palladium/charcoal

: 77-60-1
tigogenin

Conditions

Conditions	Yield
Hydrogenation;

...Expand

: 64-17-5
ethanol

: 512-04-9
diosgenin

platinum: platinum

: 77-60-1
tigogenin

Conditions

Conditions	Yield
Hydrogenation;

...Expand

: 64-19-7
acetic acid

: 512-04-9
diosgenin

platinum: platinum

: 77-60-1
tigogenin

Conditions

Conditions	Yield
Hydrogenation;

...Expand

: 7803-57-8
hydrazine hydrate

: 107-21-1
ethylene glycol

: 28404-66-2
(25R)-3β-hydroxy-5α-spirostan-23-one

potassium hydroxide: potassium hydroxide

: 77-60-1
tigogenin

Conditions

Conditions	Yield
at 195℃;

...Expand

: 71-41-0
pentan-1-ol

: 6788-40-5
(25R)-5α-Spirostan-3α-ol

sodium: sodium

: 77-60-1
tigogenin

...Expand

tobacco saponin A: tobacco saponin A

: 77-60-1
tigogenin

Conditions

Conditions	Yield
With hydrogenchloride In methanol at 37℃; for 192h;

tobacco saponin B: tobacco saponin B

: 77-60-1
tigogenin

Conditions

Conditions	Yield
With hydrogenchloride In methanol at 37℃; for 192h;

tobacco saponin C: tobacco saponin C

: 77-60-1
tigogenin

Conditions

Conditions	Yield
With hydrogenchloride In methanol at 37℃; for 192h;

: 77-60-1
tigogenin

: 124-63-0
methanesulfonyl chloride

: C28H46O5S

Conditions

Conditions	Yield
With pyridine; dmap In dichloromethane at 20℃;	100%
With pyridine for 3h;

: 77-60-1
tigogenin

: 108-24-7
acetic anhydride

: 2530-07-6
tigogenin acetate

Conditions

Conditions	Yield
With pyridine at 45℃;	99%
With dmap In tetrahydrofuran at 20℃; for 24h; Inert atmosphere;	96%

: 77-60-1
tigogenin

: 151767-11-2
2,3,4,5-tetra-O-benzoyl-D-glucopyranosyl trichloroacetimidate

: 885453-92-9
tigogenin 3β-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside)

Conditions

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve In dichloromethane at 0 - 20℃;	97%

: 77-60-1
tigogenin

: 470-07-5
tigogenone

Conditions

Conditions	Yield
With chromium(VI) oxide; sulfuric acid In acetone at 30℃; for 0.5h; Jones oxidation;	93%
With pyridinium chlorochromate In dichloromethane	90.4%
With sodium acetate; silica gel; pyridinium chlorochromate In dichloromethane at 0 - 20℃; for 15h;	87%
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane at 0 - 20℃; for 24h; Solvent;	80.2%
With oxalyl dichloride; dimethyl sulfoxide; triethylamine 1) CH2Cl2, THF, -78 deg C, 30 min, 2a) -78 deg C, 40 min, 2b) up to r.t.; Yield given. Multistep reaction;

: 77-60-1
tigogenin

A: 566-61-0
allopregnenolone

B: 2857-75-2
(R)-4-methyl-δ-valerolactone

Conditions

Conditions	Yield
Stage #1: tigogenin With acetic anhydride In acetic acid at 200℃; for 1h; Stage #2: With dihydrogen peroxide; sodium phosphotungstate In water; butan-1-ol at 80℃; for 2h; Stage #3: With sodium hydroxide In water; butan-1-ol for 2h; Product distribution / selectivity; Heating / reflux;	A 92% B 80%
Stage #1: tigogenin With acetic anhydride In acetic acid at 200℃; for 1h; Stage #2: With sulfuric acid; dihydrogen peroxide; sodium molybdate In water; N,N-dimethyl-formamide at 80℃; for 2h; Stage #3: With potassium hydroxide In water; butan-1-ol at 80℃; for 2h; Product distribution / selectivity;	A 90% B 84%
Stage #1: tigogenin With acetic anhydride In acetic acid at 200℃; for 1h; Stage #2: With dihydrogen peroxide; H7[(PMo2O7)6]*xH2O In water; acetic anhydride; acetic acid at 80℃; for 2h; Stage #3: With potassium hydroxide In ethanol; water for 2h; Product distribution / selectivity; Heating / reflux;	A 86% B 80%

: 77-60-1
tigogenin

: 999-97-3
1,1,1,3,3,3-hexamethyl-disilazane

: 156590-26-0
(3β,5α,25R)-3-trimethylsilyloxyspirostane

Conditions

Conditions	Yield
In acetonitrile for 6h; Heating;	91%

: 77-60-1
tigogenin

: 514-33-0
(16S,20S)-3β-hydroxy-23,24-bis-norcholano-22,16-lactone

Conditions

Conditions	Yield
Stage #1: tigogenin With sulfuric acid; tetrabutylammomium bromide; iodine; acetic acid; trifluoroacetic acid In dichloromethane at 50℃; for 1h; Stage #2: With dihydrogen peroxide In dichloromethane; water at 0 - 20℃; Stage #3: With water; lithium hydroxide In tetrahydrofuran; dichloromethane for 1h; Reflux;	91%
Stage #1: tigogenin With peroxyacetic acid; sulfuric acid; iodine; acetic acid In acetic anhydride at 20℃; for 24h; Stage #2: With potassium hydroxide In ethanol at 20℃; for 12h;	89%
Stage #1: tigogenin With peroxyacetic acid; sulfuric acid; iodine In acetic acid at 20℃; Stage #2: With sodium hydroxide In water; acetic acid at 20℃; pH=13;	85%
Stage #1: tigogenin With sulfuric acid; iodine; acetic acid at 20℃; for 0.166667h; Stage #2: With peracetic acid; acetic acid for 14h; Stage #3: With sodium hydroxide at 20℃; pH=13;	85%

: 77-60-1
tigogenin

: 661460-75-9
(25R)-5α-cholestane-3β,16β,26-triol

Conditions

Conditions	Yield
With hydrogenchloride; zinc In ethanol for 0.5h; Heating;	90%

: 77-60-1
tigogenin

: 149625-81-0
(1aS,3R,3aS,6aS,6bR)-3-Triisopropylsilanyloxymethyl-tetrahydro-1,2,4,6-tetraoxa-cyclopropa[e]inden-5-one

: tigogenyl 3',4'-di-O-carbonyl-6'-O-(triisopropylsilyl)-β-D-galactopyranoside

Conditions

Conditions	Yield
With zinc(II) chloride In tetrahydrofuran	89%
With zinc(II) chloride In tetrahydrofuran; diethyl ether at -78 - 25℃; for 12h; Yield given;

: 77-60-1
tigogenin

: 81058-27-7
2,3,4,6-tetra-O-pivaloyl-α-D-glucopyranosyl bromide

: 100102-42-9
<(25R)-5α-Spirostan-3β-yl>-2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranosid

Conditions

Conditions	Yield
With molecular sieve; silver carbonate In diethyl ether for 24h; Ambient temperature;	88%

: 77-60-1
tigogenin

: 149707-75-5
2,3,4,6-tetra-O-benzoyl-D-glucopyranosyl trichloroacetimidate

: 885453-92-9
tigogenin 3β-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside)

Conditions

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate In dichloromethane at 20℃; for 1h; Inert atmosphere; Molecular sieve;	87%
Stage #1: tigogenin; 2,3,4,6-tetra-O-benzoyl-D-glucopyranosyl trichloroacetimidate In dichloromethane for 1h; Molecular sieve; Inert atmosphere; Stage #2: With trimethylsilyl trifluoromethanesulfonate In dichloromethane at 0℃; for 3h; Inert atmosphere;	65%

: 77-60-1
tigogenin

: 4025-57-4
(20S)-5α-pregnan-3β,16β,20-triol

Conditions

Conditions	Yield
Stage #1: tigogenin With boron trifluoride diethyl etherate; 3-chloro-benzenecarboperoxoic acid In dichloromethane at 10℃; for 2h; Baeyer-Villiger oxidation; Stage #2: With sodium hydroxide In methanol Ring cleavage; Further stages.;	85%
With potassium sulfate; dipotassium peroxodisulfate; sulfuric acid Erhitzen des Reaktionsprodukts mit aethanol. KOH;

: 77-60-1
tigogenin

: 2,3,4-tri-O-benzoyl-β-D-xylopyranosyl-(1->3)-[2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->2)]-4,6-di-O-benzylidene-α-D-galactopyranosyl trichloroacetimidate

: 1269649-29-7
tigogenyl 2,3,4-tri-O-benzoyl-β-D-xylopyranosyl-(1->3)-[2,3,4-tri-O-acetyl-α-L-rhamnopyransyl-(1->2)]-4,6-di-O-benzylidene-β-D-galactopyranoside

Conditions

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate In dichloromethane at 0℃; for 0.666667h; Inert atmosphere;	81%

: 77-60-1
tigogenin

: 440-03-9
2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-β-D-glucopyranosyl fluoride

: 101490-77-1
tigogenin cellobioside heptaacetate (β-anomer)

Conditions

Conditions	Yield
In toluene at 112℃; for 6.5h;	75%

: 77-60-1
tigogenin

: 129823-36-5
C45H44NO7PS

: 129823-40-1
C53H70O7

Conditions

Conditions	Yield
With 4 A molecular sieve; boron trifluoride diethyl etherate In dichloromethane at -10℃; for 0.333333h;	73%

: 77-60-1
tigogenin

: 321125-08-0
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

: tigogenin-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

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate; 4 Angstroem MS In dichloromethane at -20℃;	71%

: 77-60-1
tigogenin

: 615570-19-9
3,6-di-O-benzoylated-isopropyl-β-D-1-thiogalactopyranoside

: tigogenyl 3,6-di-O-benzoyl-β-D-galactopyranoside

Conditions

Conditions	Yield
With N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate In dichloromethane at -40℃; for 0.666667h; Inert atmosphere;	71%

: 77-60-1
tigogenin

: 129823-34-3
C53H52NO8PS

: 129823-39-8
C61H78O8

Conditions

Conditions	Yield
With 4 A molecular sieve; boron trifluoride diethyl etherate In dichloromethane at -10℃; for 0.333333h;	70%

: 77-60-1
tigogenin

: 130948-37-7
C53H52NO8PS

: 129823-39-8, 130948-40-2, 130948-41-3, 130948-43-5
C61H78O8

Conditions

Conditions	Yield
With 4 A molecular sieve; boron trifluoride diethyl etherate In dichloromethane at -23℃; for 8h;	70%

: 77-60-1
tigogenin

: 2137-22-6
spirosta-Δ1,4-diene-3-one

Conditions

Conditions	Yield
With diphenyl diselenide; 3-iodylbenzoic acid In toluene for 7h; Reflux;	70%

: 77-60-1
tigogenin

: 108-24-7
acetic anhydride

: 1169-20-6
3β-acetoxy-5α-pregn-16-en-20-one

Conditions

Conditions	Yield
Multistep reaction.;	69.5%
Stage #1: tigogenin; acetic anhydride With pyridine for 1h; Reflux; Stage #2: titanium tetrachloride In acetic anhydride at 100℃; Reflux; Stage #3: With chromium(VI) oxide; acetic acid In water; acetone at 15 - 18℃;	69.5%
Stage #1: tigogenin; acetic anhydride In pyridine for 1h; Reflux; Stage #2: titanium tetrachloride In pyridine at 100℃; for 2h; Reflux; Stage #3: With chromium(VI) oxide; sodium acetate; acetic acid In pyridine; water; acetone at 15 - 18℃; for 1h;	69.5%
Stage #1: tigogenin; acetic anhydride With pyridine; ammonium chloride at 125 - 135℃; for 9h; Stage #2: With chromium(VI) oxide; water; acetic acid In 1,2-dichloro-ethane at 7 - 20℃;	55%
Stage #1: tigogenin; acetic anhydride With acetic acid at 208 - 225℃; under 3600.36 - 4875.49 Torr; for 1.08333h; Stage #2: With chromic acid at 12 - 98℃; for 0.75h; Temperature;

: 77-60-1
tigogenin

: isopropyl 2,3,6-tri-O-benzoyl-1-thio-β-D-galactopyranoside

: tigogenyl 2,3,6-tri-O-benzoyl-β-D-galactopyranoside

Conditions

Conditions	Yield
With N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate In dichloromethane at -40℃; for 0.5h; Inert atmosphere;	65%

: 77-60-1
tigogenin

: 773145-61-2
2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzoyl-α-D-glucopyranosyl trichloroacetimidate

: 1352548-84-5
3-O-[2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1→4)-2,3,6-tri-O-benzoyl-β-D-glucopyranosyl]tigogenin

Conditions

Conditions	Yield
Stage #1: tigogenin; 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzoyl-α-D-glucopyranosyl trichloroacetimidate In dichloromethane for 1h; Molecular sieve; Inert atmosphere; Stage #2: With trimethylsilyl trifluoromethanesulfonate In dichloromethane at 0℃; for 3h; Inert atmosphere;	61%

: 77-60-1
tigogenin

: 343980-32-5
(O-2,3,4,6-tetra-O-benzoyl-α-D-glucopyranosyl-(1→4)-2,3,6-tri-O-benzoyl-α-D-glucopyranosyl)-trichloroacetimidate

: 1352548-83-4
3-O-[2,3,4,6-tetra-O-benzoyl-α-D-glucopyranosyl-(1→4)-2,3,6-tri-O-benzoyl-β-D-glucopyranosyl]tigogenin

Conditions

Conditions	Yield
Stage #1: tigogenin; (O-2,3,4,6-tetra-O-benzoyl-α-D-glucopyranosyl-(1→4)-2,3,6-tri-O-benzoyl-α-D-glucopyranosyl)-trichloroacetimidate In dichloromethane for 1h; Molecular sieve; Inert atmosphere; Stage #2: With trimethylsilyl trifluoromethanesulfonate In dichloromethane at 0℃; for 3h; Inert atmosphere;	58%

: 77-60-1
tigogenin

: 6870-74-2
(3β,5α,22β,25R)-furostane-3,26-diol

Conditions

Conditions	Yield
With sodium cyanoborohydride In acetic acid for 2.5h; Ring cleavage;	55%

Tigogenin Specification

The CAS registry number of Tigogenin is 77-60-1. The systematic name is (3β,5α,25R)-spirostan-3-ol. Its EINECS registry number is 201-041-9. In addition, the molecular formula is C₂₇H₄₄O₃ and the molecular weight is 416.64. It belongs to the class of Miscellaneous Natural Products.

Physical properties about this chemical are: (1)ACD/LogP: 6.21; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 6.21; (4)ACD/LogD (pH 7.4): 6.21; (5)ACD/BCF (pH 5.5): 30645.03; (6)ACD/BCF (pH 7.4): 30645.03; (7)ACD/KOC (pH 5.5): 56613.64; (8)ACD/KOC (pH 7.4): 56613.64; (9)#H bond acceptors: 3; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 27.69 Å²; (13)Index of Refraction: 1.552; (14)Molar Refractivity: 119.65 cm³; (15)Molar Volume: 374.3 cm³; (16)Polarizability: 47.43 ×10^-24cm³; (17)Surface Tension: 43.8 dyne/cm; (18)Density: 1.11 g/cm³; (19)Flash Point: 266.2 °C; (20)Enthalpy of Vaporization: 90.78 kJ/mol; (21)Boiling Point: 516.6 °C at 760 mmHg; (22)Vapour Pressure: 7.83E-13 mmHg at 25°C.

Uses of Tigogenin: it can be used as raw materials of dehydro-methyl testosterone and rehabilitation dragons. And it can be used to get (20S)-5a-pregnanetriol-(3b.16b.20). This reaction is a kind of Baeyer-Villiger oxidation reaction. And it will need reagents MCPBA, BF₃*Et₂O and NaOH and solvents CH₂Cl₂ and methanol. The reaction time is 2 hours at reaction temperature of 10 °C. The yield is about 85%.

Tigogenin can be used to get (20S)-5a-pregnanetriol-(3b.16b.20)

You can still convert the following datas into molecular structure:
(1)SMILES: O1[C@@H]4[C@H]([C@@H]([C@]12OC[C@@H](CC2)C)C)[C@@]5(C)CC[C@@H]3[C@@]6(C)CC[C@H](O)C[C@@H]6CC[C@H]3[C@@H]5C4
(2)InChI: InChI=1/C27H44O3/c1-16-7-12-27(29-15-16)17(2)24-23(30-27)14-22-20-6-5-18-13-19(28)8-10-25(18,3)21(20)9-11-26(22,24)4/h16-24,28H,5-15H2,1-4H3/t16-,17+,18+,19+,20-,21+,22+,23+,24+,25+,26+,27-/m1/s1
(3)InChIKey: GMBQZIIUCVWOCD-MFRNJXNGBQ

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
rat	LDLo	intraperitoneal	10mg/kg (10mg/kg)		"Toxins of Animal and Plant Origin, Proceedings International Symposium, 2nd, 1970," de Vries A., and E. Kochva, eds., 3 vols., New York, Gordon and Breach Science Pub., 1971-73Vol. 2, Pg. 597, 1972.

Product Name

Tigogenin

Synthetic route

Tigogenin Specification

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