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Diosgenin CAS 512-04-9
Cas No: 512-04-9
USD $ 200.0-216.0 / Kilogram 1 Kilogram 1000 Kilogram/Month Antimex Chemical Limied Contact Supplier
E-0117 Diosgenin
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Healthy Product Dioscoreae Rhizoma Extract
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Diosgenin
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diosgenin
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Cas No: 512-04-9
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100% Pure Natural Plant Wild Yam Root Extract Diosgenin Powder 10:1
Cas No: 512-04-9
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Cas No: 512-04-9
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512-04-9 Usage

Chemical Properties

White to Off-White Dolid

Uses

pregnenolone and progesterone precursor

Purification Methods

Crystallise diosgenin from acetone, and chromatograph it on Al2O3 and elute with *C6H6/Et2O (9:1), then recrystallise it from MeOH. Its solubility is ~4% in H2O and 5% in CHCl3. The acetate crystallises from AcOH with m 198o; and has [] D 20 -119o (pyridine). [Marker et al. J Am Chem Soc 65 1199 1943. Mazur et al. J Am Chem Soc 82 5889 1960, Beilstein 19 IV 862.]

Uses

antiinflammatory, estrogen

Anticancer Research

It is a steroidal saponin and legumes and yams are the rich sources of it. It is a notoriousprecursor of several synthetic steroidal drugs. It suppresses growth of cells andinduces apoptosis in human osteosarcoma, colon cancer, and leukemia. Its anticancermechanism is by arresting the cell cycle, disrupting the calcium homeostasis,activating p53, releasing apoptosis inducing factors, and modulating caspase-3activity. It suppresses NF-κB activation induced by TNF as a result of DNA binding,IκBα kinase activation, degradation, phosphorylation, p65 nuclear translocation,and phosphorylation. It suppresses proliferation and invasion and induces apoptosisby downregulation of cFLIP, cyclin-D1, TRAF1, COX-2, c-myc, Bfl-1/A1, BclxL,IAP1, Bcl-2, and MMP-9 (Aggarwal et al. 2008; Raju and Mehta 2008).

Uses

Aglicone of saponin dioscin. Diosgenin exists in some food supplements and herbal medicines and lowers plasma cholesterol by increasing fecal cholesterol excretion. e and Progesterone.

512-04-9 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
TCI America (D1474)  Diosgenin  >95.0%(GC) 512-04-9 1g 195.00CNY Detail
TCI America (D1474)  Diosgenin  >95.0%(GC) 512-04-9 10g 690.00CNY Detail
Sigma (D1634)  Diosgenin  ≥93% 512-04-9 D1634-5G 565.11CNY Detail
Sigma (D1634)  Diosgenin  ≥93% 512-04-9 D1634-100G 6,259.50CNY Detail

512-04-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 13, 2017

Revision Date: Aug 13, 2017

1.Identification

1.1 GHS Product identifier

Product name diosgenin

1.2 Other means of identification

Product number -
Other names Spirost-5-en-3-ol, (3β,25R)-

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:512-04-9 SDS

512-04-9Synthetic route

pseudodiosgenin
6808-14-6, 7662-13-7

pseudodiosgenin

diosgenin
512-04-9

diosgenin

Conditions
ConditionsYield
With hydrogenchloride In methanol at 20℃; for 12h; Cycloaddition;100%
tert-butyldimethyl(((2’R,4S,5’R,6aR,6bS,8aS,8bR,9S,11aS,12aS,12bS)-5’,6a,8a,9-tetramethyl-1,3,3’,4,4’,5,5’,6,6a,6b,6’,7,8,8a,8b,9,11a,12,12a,12b-icosahydrospiro[naphtho[2’,1’:4,5]indeno[2,1-b]furan-10,2’-pyran]-4-yl)oxy)silane
86533-55-3

tert-butyldimethyl(((2’R,4S,5’R,6aR,6bS,8aS,8bR,9S,11aS,12aS,12bS)-5’,6a,8a,9-tetramethyl-1,3,3’,4,4’,5,5’,6,6a,6b,6’,7,8,8a,8b,9,11a,12,12a,12b-icosahydrospiro[naphtho[2’,1’:4,5]indeno[2,1-b]furan-10,2’-pyran]-4-yl)oxy)silane

diosgenin
512-04-9

diosgenin

Conditions
ConditionsYield
With chloro-methylsulfanyl-methane; water; potassium iodide In 1,4-dioxane at 50℃; for 2.3h; Catalytic behavior; Temperature; Time; Solvent; Reagent/catalyst;99%
diosgenin acetate
1061-54-7

diosgenin acetate

diosgenin
512-04-9

diosgenin

Conditions
ConditionsYield
With potassium hydrogensulfate; silica gel In methanol at 65℃; for 5h;90%
Aspergillus niger;
3-O-(tert-butyldiphenylsilyl)diosgenin
324740-29-6

3-O-(tert-butyldiphenylsilyl)diosgenin

diosgenin
512-04-9

diosgenin

Conditions
ConditionsYield
With perchloric acid on silica gel In acetonitrile at 50℃; for 0.5h; chemoselective reaction;84%
Conditions
ConditionsYield
With acetic acid at 20℃; Cycloaddition;A 68.3%
B 12.6%
diosgenin acetate
1061-54-7

diosgenin acetate

A

(25R)-5-spirostene
16863-51-7

(25R)-5-spirostene

B

diosgenin
512-04-9

diosgenin

Conditions
ConditionsYield
With tetrabutylammonium tetrafluoroborate In tetrahydrofuran Electrochemical reaction;A 53%
B 47%
Conditions
ConditionsYield
With hydrogenchloride for 2.5h; Product distribution; Heating;A n/a
B n/a
C n/a
D 50.8%
Conditions
ConditionsYield
With hydrogenchloride for 2.5h; Product distribution; Heating;A n/a
B n/a
C n/a
D 50.6%
C27H44O4

C27H44O4

diosgenin
512-04-9

diosgenin

Conditions
ConditionsYield
With silica gel50%
25R-spirost-5-en-3β-yl diphenyl phosphate
1414891-45-4

25R-spirost-5-en-3β-yl diphenyl phosphate

1,2:3,4-di-O-isopropylidene-α-D-galactopyranose
4064-06-6

1,2:3,4-di-O-isopropylidene-α-D-galactopyranose

A

3β-O-(1',2':3',4'-di-O-isopropylidene-α-D-galactopyranos-6'-yl)-(25R)-spirost-5-ene
1456599-14-6

3β-O-(1',2':3',4'-di-O-isopropylidene-α-D-galactopyranos-6'-yl)-(25R)-spirost-5-ene

B

diosgenin
512-04-9

diosgenin

Conditions
ConditionsYield
With tetrabutylammonium tetrafluoroborate In dichloromethane at 25℃; Molecular sieve; Inert atmosphere; Electrochemical reaction;A 37%
B 7%
Conditions
ConditionsYield
With sulfuric acid In ethanol; water at 80℃;1.82%
With hydrogenchloride In 1,4-dioxane; water for 2h; Heating;8 mg
Multi-step reaction with 2 steps
1: 1 N H2SO4 / aq. ethanol
2: 1 N H2SO4 / aq. ethanol
View Scheme
kryptogenin
468-99-5

kryptogenin

diosgenin
512-04-9

diosgenin

Conditions
ConditionsYield
With aluminum isopropoxide; isopropyl alcohol
Multi-step reaction with 2 steps
1: pyridine
2: propanol-(2); sodium
View Scheme
Multi-step reaction with 2 steps
1: pyridine
2: isopropyl alcohol; sodium
View Scheme
kryptogenin diacetate
7554-95-2

kryptogenin diacetate

A

(25R)-16ξ,23ξH-fesene-(5)-triol-(3β,22ξ,26)

(25R)-16ξ,23ξH-fesene-(5)-triol-(3β,22ξ,26)

B

diosgenin
512-04-9

diosgenin

Conditions
ConditionsYield
With sodium; isopropyl alcohol
ethanol
64-17-5

ethanol

(22Ξ:25R)-22.26-epoxy-cholestene-(5)-triol-(3β.16β.22)

(22Ξ:25R)-22.26-epoxy-cholestene-(5)-triol-(3β.16β.22)

acetic acid
64-19-7

acetic acid

diosgenin
512-04-9

diosgenin

kryptogenin
468-99-5

kryptogenin

aluminum isopropoxide
555-31-7

aluminum isopropoxide

isopropyl alcohol
67-63-0

isopropyl alcohol

diosgenin
512-04-9

diosgenin

yamogenin
512-06-1

yamogenin

diosgenin
512-04-9

diosgenin

Conditions
ConditionsYield
With hydrogenchloride; ethanol; water
Multi-step reaction with 2 steps
1: acetic acid anhydride
2: ethanol; HCl; water
View Scheme
(25R)-3-β-hydroxyspirost-5-en-12-one
427-28-1

(25R)-3-β-hydroxyspirost-5-en-12-one

diosgenin
512-04-9

diosgenin

Conditions
ConditionsYield
With ethanol; sodium ethanolate; hydrazine hydrate
With alkali hydroxide; hydrazine hydrate; diethylene glycol
Diosgeninmonoacetat
1180-12-7

Diosgeninmonoacetat

diosgenin
512-04-9

diosgenin

Conditions
ConditionsYield
With hydrogenchloride; ethanol; water
methanol
67-56-1

methanol

C52H86O16

C52H86O16

A

tetramethoxyarabinose

tetramethoxyarabinose

B

C35H56O8

C35H56O8

C

Methyl-(6-desoxy-2,3,4-tri-O-methyl-α-L-mannopyranosid)
35939-73-2

Methyl-(6-desoxy-2,3,4-tri-O-methyl-α-L-mannopyranosid)

D

diosgenin
512-04-9

diosgenin

Conditions
ConditionsYield
With hydrogenchloride at 100℃; for 1h;
diosgenin 3-O-<α-L-rhamnopyranosyl(1<*>2)>-<β-D-glucopyranosyl(1<*>4)>-β-D-glucopyranoside
53846-52-9, 99661-97-9, 55659-75-1

diosgenin 3-O-<α-L-rhamnopyranosyl(1<*>2)>-<β-D-glucopyranosyl(1<*>4)>-β-D-glucopyranoside

diosgenin
512-04-9

diosgenin

Conditions
ConditionsYield
With hydrogenchloride In 1,4-dioxane for 3h; Heating;
Multi-step reaction with 3 steps
1: steroidal saponin-β-glucosidase from Aspergillus flavus / aq. buffer / 50 °C / pH 5 / Enzymatic reaction
2: steroidal saponin-α-1,2-rhamnosidase from C. lunata / aq. buffer / 50 °C / pH 5 / Enzymatic reaction
3: steroidal saponin-β-glucosidase from Aspergillus flavus / aq. buffer / 50 °C / pH 5 / Enzymatic reaction
View Scheme
(3β,25R)-spirost-5-en-3-yl 6-deoxy-α-L-mannopyranosyl-(1->2)-[6-deoxy-α-L-mannopyranosyl-(1->3)]-β-D-glucopyranoside
75055-90-2

(3β,25R)-spirost-5-en-3-yl 6-deoxy-α-L-mannopyranosyl-(1->2)-[6-deoxy-α-L-mannopyranosyl-(1->3)]-β-D-glucopyranoside

A

trillin
14144-06-0

trillin

B

diosgenin
512-04-9

diosgenin

Conditions
ConditionsYield
With sulfuric acid In methanol; water at 100℃; for 10h;A 75 mg
B 60 mg
(3β,25R)-spirost-5-en-3-ol-3-O-α-L-arabinofuranosyl-(1->4)-[α-L-rhamnopyranosyl-(1->2)]-β-D-glucopyranoside
50773-41-6

(3β,25R)-spirost-5-en-3-ol-3-O-α-L-arabinofuranosyl-(1->4)-[α-L-rhamnopyranosyl-(1->2)]-β-D-glucopyranoside

A

trillin
14144-06-0

trillin

B

ophiopogonin C
19057-67-1

ophiopogonin C

C

diosgenin
512-04-9

diosgenin

Conditions
ConditionsYield
With sulfuric acid In 1,4-dioxane at 100℃; for 4h;
at 290℃; further temp.;
26-(O-β-D-glucopyranosyl)-3-β-[4-O-(β-D-glucopyranosyl)-2-O-(α-L-rhamnopyranosyl)-β-D-glucopyranosyloxy]-22,26-dihydroxyfurost-5-ene
94992-08-2

26-(O-β-D-glucopyranosyl)-3-β-[4-O-(β-D-glucopyranosyl)-2-O-(α-L-rhamnopyranosyl)-β-D-glucopyranosyloxy]-22,26-dihydroxyfurost-5-ene

diosgenin
512-04-9

diosgenin

Conditions
ConditionsYield
With hydrogenchloride In 1,4-dioxane for 3h; Heating;
diosgenin-3-O-α-L-rhamnopyranosyl-(1->2)-β-D-glucopyranoside
116481-33-5

diosgenin-3-O-α-L-rhamnopyranosyl-(1->2)-β-D-glucopyranoside

diosgenin
512-04-9

diosgenin

Conditions
ConditionsYield
With sulfuric acid In water for 3h; Heating;
Acid hydrolysis;
26-O-β-D-glucopyranosyl-22-hydroxyfurost-5-ene-3β,26-diol 3-O-α-L-rhamnopyranosyl(1<*>2)-β-D-glucopyranoside
55972-80-0

26-O-β-D-glucopyranosyl-22-hydroxyfurost-5-ene-3β,26-diol 3-O-α-L-rhamnopyranosyl(1<*>2)-β-D-glucopyranoside

diosgenin
512-04-9

diosgenin

Conditions
ConditionsYield
With hydrogenchloride In 1,4-dioxane for 3h; Heating;
permethylate of taccaoside
75050-63-4

permethylate of taccaoside

A

O4,O6-dimethyl-α-D-glucopyranose
24462-98-4

O4,O6-dimethyl-α-D-glucopyranose

C

diosgenin
512-04-9

diosgenin

Conditions
ConditionsYield
With sulfuric acid In methanol; water at 100℃; for 10h;A n/a
B n/a
C 16 mg
degalactototigonin
19108-08-8

degalactototigonin

A

(25R)-5α-spirost-5-en-3β-ol 3-O-β-D-galactopyranoside
14270-72-5

(25R)-5α-spirost-5-en-3β-ol 3-O-β-D-galactopyranoside

B

diosgenin 3-O-β-D-glucopyranosyl-(1->4)-β-D-galactopyranoside
55639-73-1, 60454-77-5, 74759-15-2, 99661-95-7, 104732-63-0, 108945-21-7, 111137-19-0, 144071-57-8

diosgenin 3-O-β-D-glucopyranosyl-(1->4)-β-D-galactopyranoside

C

(25R)-spirost-5-en-3β-ol 3-O-β-D-glucopyranosyl-(1->2)-β-D-glucopyranosyl-(1->4)-β-D-galactopyranoside
60454-78-6

(25R)-spirost-5-en-3β-ol 3-O-β-D-glucopyranosyl-(1->2)-β-D-glucopyranosyl-(1->4)-β-D-galactopyranoside

D

diosgenin
512-04-9

diosgenin

Conditions
ConditionsYield
With hydrogenchloride In 1,4-dioxane; water for 1h; Heating;A 120 mg
B 170 mg
C 320 mg
D 140 mg
deltonin per-O-methylate
94901-56-1

deltonin per-O-methylate

diosgenin
512-04-9

diosgenin

Conditions
ConditionsYield
With hydrogenchloride In methanol for 2h; Heating;
C61H102O20
50773-46-1

C61H102O20

diosgenin
512-04-9

diosgenin

Conditions
ConditionsYield
With hydrogenchloride In methanol for 2h; Heating;
rhapissaponin
94898-69-8

rhapissaponin

diosgenin
512-04-9

diosgenin

Conditions
ConditionsYield
With hydrogenchloride In 1,4-dioxane; water for 2h; Heating;2 mg
p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

diosgenin
512-04-9

diosgenin

(25R)-3β-O-(p-toluenesulfonyloxy)spirost-5-ene
4965-78-0

(25R)-3β-O-(p-toluenesulfonyloxy)spirost-5-ene

Conditions
ConditionsYield
With pyridine In dichloromethane for 3h; Darkness;100%
With pyridine at 20℃; for 6h;97.7%
With pyridine
2,3,4,6-tetra-O-benzoyl-D-glucopyranosyl trichloroacetimidate
149707-75-5

2,3,4,6-tetra-O-benzoyl-D-glucopyranosyl trichloroacetimidate

diosgenin
512-04-9

diosgenin

trillin
14144-06-0

trillin

Conditions
ConditionsYield
Stage #1: 2,3,4,6-tetra-O-benzoyl-D-glucopyranosyl trichloroacetimidate; diosgenin With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve In dichloromethane at 20℃; for 0.25h; Glycosylation;
Stage #2: With sodium methylate Substitution;
100%
C41H40Cl3NO16

C41H40Cl3NO16

diosgenin
512-04-9

diosgenin

C39H62O12

C39H62O12

Conditions
ConditionsYield
Stage #1: C41H40Cl3NO16; diosgenin With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve In dichloromethane at 20℃; for 0.25h; Glycosylation;
Stage #2: With sodium methylate Substitution;
100%
benzoyl chloride
98-88-4

benzoyl chloride

diosgenin
512-04-9

diosgenin

diosgenin benzoate
4952-68-5

diosgenin benzoate

Conditions
ConditionsYield
With pyridine In dichloromethane at 20℃; for 12h;100%
succinic acid anhydride
108-30-5

succinic acid anhydride

diosgenin
512-04-9

diosgenin

4-(((25R)-spirost-5-ene-3β-yl)oxy)-4-oxobutanoic acid
4965-84-8

4-(((25R)-spirost-5-ene-3β-yl)oxy)-4-oxobutanoic acid

Conditions
ConditionsYield
With pyridine at 80℃;100%
With dmap In toluene at 80℃;99.2%
With dmap; triethylamine In dichloromethane at 80℃; for 72h;94%
acetyl chloride
75-36-5

acetyl chloride

diosgenin
512-04-9

diosgenin

(25R)-16,26-diacetoxy-4-cholesten-3,22-dione

(25R)-16,26-diacetoxy-4-cholesten-3,22-dione

Conditions
ConditionsYield
With pyridine at 20℃; for 0.5h;100%
bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

diosgenin
512-04-9

diosgenin

diosgenyl chloroformate
1337989-08-8

diosgenyl chloroformate

Conditions
ConditionsYield
Stage #1: bis(trichloromethyl) carbonate; diosgenin In tetrahydrofuran at 20℃;
Stage #2: With pyridine In tetrahydrofuran at 0℃; for 1h;
100%
In tetrahydrofuran at 0 - 20℃; for 6h;70%
With pyridine In dichloromethane at 20℃; for 3h; Inert atmosphere;
In dichloromethane
acetic anhydride
108-24-7

acetic anhydride

diosgenin
512-04-9

diosgenin

diosgenin acetate
1061-54-7

diosgenin acetate

Conditions
ConditionsYield
With pyridine In dichloromethane99%
With pyridine In dichloromethane at 20℃; for 6h;97%
With pyridine In dichloromethane at 20℃; for 6h;97%
tert-butylchlorodiphenylsilane
58479-61-1

tert-butylchlorodiphenylsilane

diosgenin
512-04-9

diosgenin

3-O-(tert-butyldiphenylsilyl)diosgenin
324740-29-6

3-O-(tert-butyldiphenylsilyl)diosgenin

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide at 20℃;99%
With 1H-imidazole In N,N-dimethyl-formamide96%
With 1H-imidazole In dichloromethane at 20℃; for 12h;93%
tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

diosgenin
512-04-9

diosgenin

tert-butyldimethyl(((2’R,4S,5’R,6aR,6bS,8aS,8bR,9S,11aS,12aS,12bS)-5’,6a,8a,9-tetramethyl-1,3,3’,4,4’,5,5’,6,6a,6b,6’,7,8,8a,8b,9,11a,12,12a,12b-icosahydrospiro[naphtho[2’,1’:4,5]indeno[2,1-b]furan-10,2’-pyran]-4-yl)oxy)silane
86533-55-3

tert-butyldimethyl(((2’R,4S,5’R,6aR,6bS,8aS,8bR,9S,11aS,12aS,12bS)-5’,6a,8a,9-tetramethyl-1,3,3’,4,4’,5,5’,6,6a,6b,6’,7,8,8a,8b,9,11a,12,12a,12b-icosahydrospiro[naphtho[2’,1’:4,5]indeno[2,1-b]furan-10,2’-pyran]-4-yl)oxy)silane

Conditions
ConditionsYield
With 1H-imidazole In dichloromethane; N,N-dimethyl-formamide at 20℃; for 2h; Inert atmosphere;99%
With 1H-imidazole; dmap In N,N-dimethyl-formamide at 50℃; for 0.5h;99%
With 1H-imidazole; dmap In N,N-dimethyl-formamide at 50℃; for 0.5h;98%
diosgenin
512-04-9

diosgenin

tigogenin
77-60-1

tigogenin

Conditions
ConditionsYield
With hydrogen; palladium dihydroxide In ethanol; dichloromethane99%
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;
2,3,4,6-tetra-O-benzoyl-D-glucopyranosyl ortho-(hex-1-ynyl)benzoate
1221151-98-9

2,3,4,6-tetra-O-benzoyl-D-glucopyranosyl ortho-(hex-1-ynyl)benzoate

diosgenin
512-04-9

diosgenin

diosgenyl 2,3,4,6-O-tetra-benzoyl-β-D-glucuronopyranoside
120969-06-4

diosgenyl 2,3,4,6-O-tetra-benzoyl-β-D-glucuronopyranoside

Conditions
ConditionsYield
trifluoromethanesulfonyloxy(triphenylphosphine)gold(I) In dichloromethane at 20℃;99%
3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl chloride
7772-87-4

3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl chloride

diosgenin
512-04-9

diosgenin

diosgenin 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranoside
575458-79-6

diosgenin 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Conditions
ConditionsYield
Stage #1: diosgenin With 2,4,6-trimethyl-pyridine; silver trifluoromethanesulfonate In dichloromethane at 20℃; for 0.166667h; Molecular sieve; Inert atmosphere;
Stage #2: 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl chloride In dichloromethane at 20℃; for 20h; Molecular sieve; Inert atmosphere;
99%
3,4,6-tri-O-benzyl-2-deoxy-2-(o-nitrobenzenesulfonylamino)-α-D-glucopyranosyl ortho-hexynylbenzoate

3,4,6-tri-O-benzyl-2-deoxy-2-(o-nitrobenzenesulfonylamino)-α-D-glucopyranosyl ortho-hexynylbenzoate

diosgenin
512-04-9

diosgenin

diosgenyl 3,4,6-tri-O-benzyl-2-deoxy-2-(2-dinitrobenzenesulfonylamino)-β-D-glucopyranoside

diosgenyl 3,4,6-tri-O-benzyl-2-deoxy-2-(2-dinitrobenzenesulfonylamino)-β-D-glucopyranoside

Conditions
ConditionsYield
With (triphenyl phosphite)gold(I) chloride; silver tetrakis(pentafluorophenyl)borate In dichloromethane at 0℃; for 0.5h; Molecular sieve;99%
acetic anhydride
108-24-7

acetic anhydride

diosgenin
512-04-9

diosgenin

pseudodiosgenin diacetate
2309-38-8

pseudodiosgenin diacetate

Conditions
ConditionsYield
Stage #1: acetic anhydride With aluminum (III) chloride at 20℃; for 0.25h; Green chemistry;
Stage #2: diosgenin at 140℃; for 3h; Reagent/catalyst; Green chemistry;
98%
With pyridine; ammonium chloride Reflux;86%
Ring cleavage; acetylation; Heating;56.3%
benzyl bromide
100-39-0

benzyl bromide

diosgenin
512-04-9

diosgenin

3-O-benzyl diosgenin
146333-24-6

3-O-benzyl diosgenin

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran; N,N-dimethyl-formamide at 90℃;98%
Stage #1: diosgenin With sodium hydride In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 1h;
Stage #2: benzyl bromide In tetrahydrofuran; N,N-dimethyl-formamide Heating; Further stages.;
97%
With sodium hydride In tetrahydrofuran; N,N-dimethyl-formamide Heating;96%
With tetra-(n-butyl)ammonium iodide; sodium hydride In tetrahydrofuran for 16h; Heating;90%
With sodium hydride
3,4,6-Tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranosyl bromide
67124-60-1

3,4,6-Tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranosyl bromide

diosgenin
512-04-9

diosgenin

diosgenyl 3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxy-carbonylamino)-β-D-glucopyranoside
1028758-82-8

diosgenyl 3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxy-carbonylamino)-β-D-glucopyranoside

Conditions
ConditionsYield
Stage #1: diosgenin With silver trifluoromethanesulfonate In diethyl ether; dichloromethane at 20℃; for 0.166667h; Inert atmosphere;
Stage #2: 3,4,6-Tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranosyl bromide In diethyl ether; dichloromethane at 20℃; for 20h; Inert atmosphere;
98%
N-(tert-butyloxycarbonyl)-L-isoleucine
13139-16-7

N-(tert-butyloxycarbonyl)-L-isoleucine

diosgenin
512-04-9

diosgenin

(25R)-spirost-5-en-3β-yl N-(t-butoxycarbonyl)-L-isoleucinate

(25R)-spirost-5-en-3β-yl N-(t-butoxycarbonyl)-L-isoleucinate

Conditions
ConditionsYield
Stage #1: N-(tert-butyloxycarbonyl)-L-isoleucine With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 0.166667h;
Stage #2: diosgenin In dichloromethane at 20℃; for 24h;
98%
t-Boc-L-valine
13734-41-3

t-Boc-L-valine

diosgenin
512-04-9

diosgenin

(25R)-spirost-5-en-3β-yl N-(t-butoxycarbonyl)-L-valinate

(25R)-spirost-5-en-3β-yl N-(t-butoxycarbonyl)-L-valinate

Conditions
ConditionsYield
Stage #1: t-Boc-L-valine With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 0.166667h;
Stage #2: diosgenin In dichloromethane at 20℃; for 24h;
98%
N-tert-butoxycarbonyl-L-methionine
2488-15-5

N-tert-butoxycarbonyl-L-methionine

diosgenin
512-04-9

diosgenin

(25R)-spirost-5-en-3β-yl N-(t-butoxycarbonyl)-L-methioninate

(25R)-spirost-5-en-3β-yl N-(t-butoxycarbonyl)-L-methioninate

Conditions
ConditionsYield
Stage #1: N-tert-butoxycarbonyl-L-methionine With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 0.166667h;
Stage #2: diosgenin In dichloromethane at 20℃; for 24h;
98%
diosgenin
512-04-9

diosgenin

(22R)-16β,22-epoxycholest-5-ene-3β,26-diol
6877-70-9

(22R)-16β,22-epoxycholest-5-ene-3β,26-diol

Conditions
ConditionsYield
With sodium cyanoborohydride In acetic acid for 2.5h; Ring cleavage;97%
With sodium cyanoborohydride; propionic acid at 30℃; for 40h; Time; Inert atmosphere;78%
With lithium aluminium tetrahydride; aluminium trichloride In diethyl ether59%
Multi-step reaction with 2 steps
1: DMAP; Et3N
2: LiAlH4; AlCl3
View Scheme
Multi-step reaction with 4 steps
1: DMAP; Et3N
2: LiAlH4; AlCl3
3: pyridine
4: 32 percent / aq. tetrabutylammonium tetrafluoroborate / tetrahydrofuran / Electrochemical reaction
View Scheme
2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl N-tosyl benzimidate
1393471-65-2

2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl N-tosyl benzimidate

diosgenin
512-04-9

diosgenin

diosgenyl 2,3,4-tri-O-benzoyl-α-L-rhamnoside
869884-32-2

diosgenyl 2,3,4-tri-O-benzoyl-α-L-rhamnoside

Conditions
ConditionsYield
Stage #1: 2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl N-tosyl benzimidate; diosgenin In dichloromethane for 0.5h; Molecular sieve; Inert atmosphere;
Stage #2: With trimethylsilyl trifluoromethanesulfonate In dichloromethane at 0℃; for 2h; Molecular sieve; Inert atmosphere;
97%
diosgen-3-yl ortho-hexynylbenzoate

diosgen-3-yl ortho-hexynylbenzoate

diosgenin
512-04-9

diosgenin

3,3'-oxybis-(3β,25R)-(3'β,25'R)-spirost-5-ene

3,3'-oxybis-(3β,25R)-(3'β,25'R)-spirost-5-ene

Conditions
ConditionsYield
With (triphenyl phosphite)gold(I) chloride; silver tetrakis(pentafluorophenyl)borate at 80℃; Inert atmosphere; Molecular sieve; Darkness;97%
3,4,6-tri-O-benzyl-2-deoxy-2-(p-nitrobenzenesulfonylamino)-α-D-glucopyranosyl ortho-hexynylbenzoate

3,4,6-tri-O-benzyl-2-deoxy-2-(p-nitrobenzenesulfonylamino)-α-D-glucopyranosyl ortho-hexynylbenzoate

diosgenin
512-04-9

diosgenin

diosgenyl 3,4,6-tri-O-benzyl-2-deoxy-2-(p-nitrobenzenesulfonylamino)-β-D-glucopyranoside

diosgenyl 3,4,6-tri-O-benzyl-2-deoxy-2-(p-nitrobenzenesulfonylamino)-β-D-glucopyranoside

Conditions
ConditionsYield
With (triphenyl phosphite)gold(I) chloride; silver tetrakis(pentafluorophenyl)borate In dichloromethane at 0℃; for 0.5h; Molecular sieve;97%
benzyl bromide
100-39-0

benzyl bromide

diosgenin
512-04-9

diosgenin

diosgenin-3-benzyl ether

diosgenin-3-benzyl ether

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran; N,N-dimethyl-formamide at 100℃; under 760.051 Torr; for 0.5h; Concentration;96.2%
3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-(α/β)-D-glucopyranosyl trichloroacetimidate
146728-55-4

3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-(α/β)-D-glucopyranosyl trichloroacetimidate

diosgenin
512-04-9

diosgenin

diosgenin 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranoside
575458-79-6

diosgenin 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Conditions
ConditionsYield
With trimethylsilyl trifluoromethanesulfonate In dichloromethane at -20℃; for 1h; Molecular sieve;96%
acetic anhydride
108-24-7

acetic anhydride

diosgenin
512-04-9

diosgenin

(25R)-23-acetyl-3,16-diacetoxy-22,23-pyran-cholesta-5,22-diene

(25R)-23-acetyl-3,16-diacetoxy-22,23-pyran-cholesta-5,22-diene

Conditions
ConditionsYield
With zinc(II) chloride at 20℃; for 72h;96%
acetic anhydride
108-24-7

acetic anhydride

diosgenin
512-04-9

diosgenin

(20S,25R)-23-acetyl-22,26-epoxycholesta-5,22-diene-3β,16β-diyl diacetate
245124-64-5

(20S,25R)-23-acetyl-22,26-epoxycholesta-5,22-diene-3β,16β-diyl diacetate

Conditions
ConditionsYield
With zinc(II) chloride at 20℃; for 40h;95%
With boron trifluoride diethyl etherate at 20℃; for 0.833333h; Ring cleavage; acetylation;85%
With boron trifluoride diethyl etherate at 20℃; for 0.166667h;85%
With boron trifluoride diethyl etherate
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