• Name

  Spirostan-6-one, 3,5-dihydroxy-, (3b,5a,25R)-

• EINECS 1312995-182-4
• CAS No. 56786-63-1
• Article Data5
• CAS DataBase
• Density 1.21±0.1 g/cm3 (20 oC 760 Torr)
• Solubility (0.025 g/L) (25 oC)
• Melting Point 268-270 oC (ethanol )
• Formula C27H42O5
• Boiling Point 578.4±50.0 °C(Predicted)
• Molecular Weight 446.627
• Flash Point
• Transport Information
• Appearance White or off-white powder
• Safety
• Risk Codes
• Molecular Structure
• Hazard Symbols
• Synonyms (3beta,5alpha,25R)-3,5-Dihydroxyspirostan-6-one;BB 16;Biobras 16;Brassinosteroid BB 16;DI 31;
• PSA 75.99000
• LogP 4.08770

Synthetic route

127128-79-4

(25R)-3α,5-cyclo-5α-spirostan-6-one

56786-63-1

(25R)-3β,5-dihydroxy-5α-spirostan-6-one

Conditions

Conditions	Yield
With acetic acid for 2h; Heating;	98%

5874-17-9

(25R)-3β-acetoxy-5-hydroxy-5α-spirostan-6-one

56786-63-1

(25R)-3β,5-dihydroxy-5α-spirostan-6-one

Conditions

Conditions	Yield
With sodium hydrogencarbonate In methanol; water for 3h; Reflux;	95%

56816-69-4

(25R)-spirostan-22α-O-3β,5α,6β-triol

56786-63-1

(25R)-3β,5-dihydroxy-5α-spirostan-6-one

Conditions

Conditions	Yield
With N-Bromosuccinimide In 1,4-dioxane; water at 20℃; for 2h; Darkness;	83%
Multi-step reaction with 3 steps 1: 84 percent / imidazole / dimethylformamide / 3 h 2: PCC / CH2Cl2 / 0 - 20 °C 3: 7.14 g / TBFA / tetrahydrofuran / 6 h View Scheme

C33H56O5Si

56786-63-1

(25R)-3β,5-dihydroxy-5α-spirostan-6-one

Conditions

Conditions	Yield
With TBFA In tetrahydrofuran for 6h;	7.14 g

876908-18-8

(25R)-3β-(t-butyldimethylsilyloxy)-5α-spirostane-5,6β-diol

56786-63-1

(25R)-3β,5-dihydroxy-5α-spirostan-6-one

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: PCC / CH2Cl2 / 0 - 20 °C 2: 7.14 g / TBFA / tetrahydrofuran / 6 h View Scheme

5,6-epoxyspirostane

56786-63-1

(25R)-3β,5-dihydroxy-5α-spirostan-6-one

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: perchloric acid / water; tetrahydrofuran / 3 h / 20 °C 2: N-Bromosuccinimide / water; 1,4-dioxane / 2 h / 20 °C / Darkness View Scheme

56786-63-1

(25R)-3β,5-dihydroxy-5α-spirostan-6-one

149707-75-5

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

1373440-75-5

5α-hydroxylaxogenyl 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;	94%

98-59-9

p-toluenesulfonyl chloride

56786-63-1

(25R)-3β,5-dihydroxy-5α-spirostan-6-one

(25R)-6-oxo-3β-(p-toluenesulfonyloxy)-5α-spirostane

Conditions

Conditions	Yield
With pyridine at 20℃; for 24h;	88%
With pyridine at 20℃; for 24h;
With pyridine at 20℃;
With pyridine

20295-82-3

O-carboxymethylhydroxylamine hydrochloride

56786-63-1

(25R)-3β,5-dihydroxy-5α-spirostan-6-one

(25R)-6E-[O-(carboxymethyl)oximino]-5-hydroxy-5α-spirostan-3β-ol

Conditions

Conditions	Yield
With pyridine at 20℃;	88%

56786-63-1

(25R)-3β,5-dihydroxy-5α-spirostan-6-one

74395-54-3

(25R)-5α-hydroxy-5α-spirosta-3,6-dione

Conditions

Conditions	Yield
With Jones reagent In water; acetone at 20℃;	81.5%

56786-63-1

(25R)-3β,5-dihydroxy-5α-spirostan-6-one

876908-20-2

(25R)-3β,5-dihydroxy-5β-spirostan-6-one

Conditions

Conditions	Yield
With potassium hydroxide In methanol for 24h; Heating;	74%

103-71-9

phenyl isocyanate

56786-63-1

(25R)-3β,5-dihydroxy-5α-spirostan-6-one

(25R)-5α-hydroxy-6-oxo-spirostan-3β-yl phenylcarbamate

Conditions

Conditions	Yield
With hydrogenchloride In chloroform; water for 24h; Reflux;	68%

56786-63-1

(25R)-3β,5-dihydroxy-5α-spirostan-6-one

74-88-4

methyl iodide

83110-94-5

6β-methyl-5α-(25R)-spirostane-3β,5,6α-triol

Conditions

Conditions	Yield
With magnesium 1.) ether, 2.) THF, 3 h, reflux; Yield given. Multistep reaction;

64-18-6

formic acid

56786-63-1

(25R)-3β,5-dihydroxy-5α-spirostan-6-one

C28H42O6

Conditions

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 24h; Mitsunobu reaction;

75-75-2

methanesulfonic acid

56786-63-1

(25R)-3β,5-dihydroxy-5α-spirostan-6-one

C28H44O7S

Conditions

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 40℃; for 24h; Mitsunobu reaction;
With dmap; di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 48.25h; Mitsunobu reaction; Inert atmosphere;

108-24-7

acetic anhydride

56786-63-1

(25R)-3β,5-dihydroxy-5α-spirostan-6-one

5874-17-9

(25R)-3β-acetoxy-5-hydroxy-5α-spirostan-6-one

Conditions

Conditions	Yield
With pyridine at 20℃;

56786-63-1

(25R)-3β,5-dihydroxy-5α-spirostan-6-one

325125-66-4

C27H40O5

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridine / 20 °C 2: 2.03 g / Jones reagent / acetone / 2 h / Heating View Scheme

56786-63-1

(25R)-3β,5-dihydroxy-5α-spirostan-6-one

C27H42O5

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: pyridine / 20 °C 2: 2.03 g / Jones reagent / acetone / 2 h / Heating 3: H2 / Pd/C / ethanol / 24 h View Scheme

56786-63-1

(25R)-3β,5-dihydroxy-5α-spirostan-6-one

909879-88-5

(25R)-5,6-seco-A-homo-5(10)-oxa-5-oxo-spirostan-6-oic acid

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: pyridine / 20 °C 2: 2.03 g / Jones reagent / acetone / 2 h / Heating 3: H2 / Pd/C / ethanol / 24 h 4: 1.54 g / mCPBA / CH2Cl2 / 20 °C View Scheme

56786-63-1

(25R)-3β,5-dihydroxy-5α-spirostan-6-one

C47H69N3O12

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: pyridine / 20 °C 2: 2.03 g / Jones reagent / acetone / 2 h / Heating 3: H2 / Pd/C / ethanol / 24 h 4: 1.54 g / mCPBA / CH2Cl2 / 20 °C 5: 1.1 g / methanol / 20 °C View Scheme

56786-63-1

(25R)-3β,5-dihydroxy-5α-spirostan-6-one

321857-67-4

(25R)-5-hydroxy-5α-spirostan-6-one

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 88 percent / pyridine / 24 h / 20 °C 2: 90 percent / LiBr; Li2CO3 / dimethylformamide / 1 h / Heating View Scheme
Multi-step reaction with 2 steps 1: pyridine / 24 h / 20 °C 2: 2.29 g / LiBr; Li2CO3 / dimethylformamide / 2 h / Heating View Scheme

56786-63-1

(25R)-3β,5-dihydroxy-5α-spirostan-6-one

(25R)-2α,3α,5-trihydroxy-5α-spirostan-6-one

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 88 percent / pyridine / 24 h / 20 °C 2: 90 percent / LiBr; Li2CO3 / dimethylformamide / 1 h / Heating 3: 91 percent / OsO4 / N-methylmorpholine N-oxide / 2-methyl-propan-2-ol; tetrahydrofuran; H2O / 24 h / 20 °C View Scheme

56786-63-1

(25R)-3β,5-dihydroxy-5α-spirostan-6-one

(25R)-3β-amino-5-hydroxy-5α-spirostan-6-one

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: Ph3P; DIAD / tetrahydrofuran / 24 h / 40 °C 2: 595 mg / NaN3 / various solvent(s) / 48 h / 50 °C 3: H2 / Lindlar catalyst / ethanol / 36 h View Scheme

56786-63-1

(25R)-3β,5-dihydroxy-5α-spirostan-6-one

(25R)-3β-amino-5-hydroxy-5β-spirostan-6-one

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: Ph3P; DIAD / tetrahydrofuran / 24 h / 40 °C 2: 595 mg / NaN3 / various solvent(s) / 48 h / 50 °C 3: H2 / Lindlar catalyst / ethanol / 36 h 4: 620 mg / Et3N / dioxane / 20 h 5: KOH / methanol / 24 h / Heating 6: 313 mg / CF3CO2H / CH2Cl2 / 0.17 h View Scheme

56786-63-1

(25R)-3β,5-dihydroxy-5α-spirostan-6-one

876908-24-6

(25R)-2β,3β-epoxy-5-hydroxy-5β-spirostan-6-one

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 74 percent / KOH / methanol / 24 h / Heating 2: pyridine / 24 h / 20 °C 3: 2.36 g / Li2CO3; LiBr / dimethylformamide / 2 h / Heating 4: 48 percent / mCPBA / CH2Cl2 / 0 - 20 °C View Scheme

56786-63-1

(25R)-3β,5-dihydroxy-5α-spirostan-6-one

876908-23-5

(25R)-2α,3α-epoxy-5-hydroxy-5β-spirostan-6-one

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 74 percent / KOH / methanol / 24 h / Heating 2: pyridine / 24 h / 20 °C 3: 2.36 g / Li2CO3; LiBr / dimethylformamide / 2 h / Heating 4: 24 percent / mCPBA / CH2Cl2 / 0 - 20 °C View Scheme

56786-63-1

(25R)-3β,5-dihydroxy-5α-spirostan-6-one

876908-19-9

(25R)-3α,5-dihydroxy-5α-spirostan-6-one

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: Ph3P; DIAD / tetrahydrofuran / 24 h / 20 °C 2: 800 mg / NaHCO3 / methanol; H2O / 1 h / 20 °C View Scheme

56786-63-1

(25R)-3β,5-dihydroxy-5α-spirostan-6-one

(25R)-3α,5-dihydroxy-5β-spirostan-6-one

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: Ph3P; DIAD / tetrahydrofuran / 24 h / 20 °C 2: 800 mg / NaHCO3 / methanol; H2O / 1 h / 20 °C 3: 71 percent / KOH / methanol / 24 h / Heating View Scheme

56786-63-1

(25R)-3β,5-dihydroxy-5α-spirostan-6-one

876908-28-0

(25R)-3β-azido-5-hydroxy-5α-spirostan-6-one

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: Ph3P; DIAD / tetrahydrofuran / 24 h / 40 °C 2: 595 mg / NaN3 / various solvent(s) / 48 h / 50 °C View Scheme
Multi-step reaction with 2 steps 1: dmap; di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 48.25 h / 20 °C / Inert atmosphere 2: sodium azide / 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / 48 h / 20 °C / Inert atmosphere View Scheme

56786-63-1

(25R)-3β,5-dihydroxy-5α-spirostan-6-one

705941-87-3

(25R)-2β,3β,5-trihydroxy-5α-spirostan-6-one

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: pyridine / 24 h / 20 °C 2.1: 2.29 g / LiBr; Li2CO3 / dimethylformamide / 2 h / Heating 3.1: AcOAg; I2 / acetic acid; H2O / 3 h / Heating 3.2: 61 percent / KOH / methanol / 0.5 h / Heating View Scheme

56786-63-1

(25R)-3β,5-dihydroxy-5α-spirostan-6-one

876908-22-4

(25R)-2β,3β,5-trihydroxy-5β-spirostan-6-one

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 74 percent / KOH / methanol / 24 h / Heating 2: pyridine / 24 h / 20 °C 3: 2.36 g / Li2CO3; LiBr / dimethylformamide / 2 h / Heating 4: 68 percent / NMO; OsO4 / tetrahydrofuran; 2-methyl-propan-2-ol; H2O / 24 h / 20 °C View Scheme