(25R)-26-O-β-D-glucopyranosyl-furosta-5,20(22)-diene-1β,3β,26-triol 1-O-[α-L-rhamnopyranosyl-(1->2)-O-α-L-arabinopyranoside]
(25R)-ruscogenin
Conditions | Yield |
---|---|
With β-glucosidase In phosphoric acid at 37℃; for 24h; Enzymatic reaction; |
Conditions | Yield |
---|---|
With hydrogenchloride In 1,4-dioxane; water at 95℃; for 1h; Inert atmosphere; | A n/a B 3.8 mg |
Conditions | Yield |
---|---|
With hydrogenchloride In 1,4-dioxane; water at 95℃; for 1h; Inert atmosphere; | A n/a B n/a C 2.8 mg |
Conditions | Yield |
---|---|
With hydrogenchloride In 1,4-dioxane; water at 95℃; for 1h; Inert atmosphere; | A n/a B n/a C 1.5 mg |
3β-O-tert-butyldimethylsilyl-(25R)-ruscogenin
(25R)-ruscogenin
Conditions | Yield |
---|---|
With hydrogenchloride In acetone for 1h; Ambient temperature; | 96% |
With hydrogenchloride at 20℃; for 1h; | 96% |
3β-acetoxyspirost-5-ene-1-one
A
(20S,22R,25R)-1α,3β-dihydroxyspirost-5-ene
B
(25R)-ruscogenin
Conditions | Yield |
---|---|
With lithium tri-t-butoxyaluminum hydride In tetrahydrofuran cooling 1 h, r.t., 1 h; | A 66% B 34% |
With LTBH In tetrahydrofuran cooling 1 h, r.t., 1 h; | A 66% B 34% |
(25R)-ruscogenin
Conditions | Yield |
---|---|
With hydrogenchloride In 1,4-dioxane at 95℃; for 1h; | 11.2 mg |
With hydrogenchloride In methanol at 80℃; for 10h; Sealed tube; | 0.6 mg |
spirost-5-ene-1-oxo-3β-ol
A
(20S,22R,25R)-1α,3β-dihydroxyspirost-5-ene
B
(25R)-ruscogenin
Conditions | Yield |
---|---|
With sodium tetrahydroborate In methanol for 2h; Ambient temperature; | A 70% B 30% |
With lithium tri-t-butoxyaluminum hydride In tetrahydrofuran cooling 1 h, r.t., 1 h; | A 60% B 40% |
(25R)-ruscogenin
Conditions | Yield |
---|---|
With hydrogenchloride In methanol for 3h; Heating; |
spirosta-5(6),25(27)-diene-1β,3β-diol
(25R)-ruscogenin
Conditions | Yield |
---|---|
palladium on activated charcoal In ethanol; cyclohexene for 16h; Heating; Yield given; |
(25R)-ruscogenin
Conditions | Yield |
---|---|
With hydrogenchloride In 1,4-dioxane for 3h; Heating; |
(25R)-ruscogenin
Conditions | Yield |
---|---|
With hydrogenchloride In 1,4-dioxane for 3h; Heating; |
(2S,3R,4R,5R,6S)-2-[(2R,3R,4S,5S,6R)-5-hydroxy-2-[(1S,2S,4S,5′R,6R,7S,8R,9S,12S,13R,14R,16R)-16-hydroxy-5′,7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene-6,2′-oxane]-14-yl]oxy-6-methyl-4-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-3-yl]oxy-6-methyloxane-3,4,5-triol
(25R)-ruscogenin
Conditions | Yield |
---|---|
With hydrogenchloride In 1,4-dioxane; water for 2h; Heating; |
ruscogenin 1-O-α-L-rhamnopyranosyl(1->2)-4-O-sulfo-β-D-fucopyranoside
(25R)-ruscogenin
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: pyridine; dioxane / 7 h / 80 °C 2: 2 N HCl / dioxane; H2O / 2 h / Heating View Scheme |
26-O-β-D-glucopyranosyl 22-hydroxy-25(R)-furost-5-en-1β,3β,26-triol 1-O-α-L-rhamnopyranosyl(1->2)-4-O-sulfo-β-D-fucopyranoside
(25R)-ruscogenin
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: H2O / 24 h / 37 °C / almond emulsin 2: pyridine; dioxane / 7 h / 80 °C 3: 2 N HCl / dioxane; H2O / 2 h / Heating View Scheme |
(25R)-ruscogenin
Conditions | Yield |
---|---|
With hydrogenchloride; dipotassium hydrogenphosphate; 2,3,4,5,6-pentahydroxy-hexanal; sodium chloride In water; dimethyl sulfoxide at 120℃; pH=7; Autoclave; Microbiological reaction; |
(25R)-ruscogenin
Conditions | Yield |
---|---|
With hydrogenchloride; dipotassium hydrogenphosphate; 2,3,4,5,6-pentahydroxy-hexanal; sodium chloride In water; dimethyl sulfoxide at 120℃; pH=7; Autoclave; Microbiological reaction; |
(25R)-ruscogenin
spirost-5-ene-1-oxo-3β-ol
Conditions | Yield |
---|---|
With pyridinium chlorochromate In dichloromethane for 2.5h; Ambient temperature; | 95% |
With chromium(VI) oxide; acetic acid |
Conditions | Yield |
---|---|
With UGT74AN1; magnesium chloride In aq. buffer at 37℃; for 12h; pH=8; Enzymatic reaction; |
(25R)-ruscogenin
Cholest-5-ene-1β,3β,16β,26-tetrol
Conditions | Yield |
---|---|
With hydrogenchloride; amalgamated zinc In ethanol for 2.5h; Heating; | 33% |
(25R)-ruscogenin
3β-acetoxyspirost-5-ene-1-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 95 percent / pyridinium chlorochromate / CH2Cl2 / 2.5 h / Ambient temperature 2: 87.5 percent / acetylation View Scheme | |
Multi-step reaction with 2 steps 1: chromium (VI)-oxide; aqueous acetic acid View Scheme |
(25R)-ruscogenin
(20S,22R,25R)-1α,3β-diacetoxyspirost-5-ene
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 95 percent / pyridinium chlorochromate / CH2Cl2 / 2.5 h / Ambient temperature 2: 70 percent / sodium borohydride / methanol / 2 h / Ambient temperature 3: 72 percent / acetylation View Scheme | |
Multi-step reaction with 4 steps 1: 95 percent / pyridinium chlorochromate / CH2Cl2 / 2.5 h / Ambient temperature 2: 87.5 percent / acetylation 3: 66 percent / LTBH / tetrahydrofuran / cooling 1 h, r.t., 1 h 4: 72 percent / acetylation View Scheme |
(25R)-ruscogenin
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 95 percent / pyridinium chlorochromate / CH2Cl2 / 2.5 h / Ambient temperature 2: 70 percent / sodium borohydride / methanol / 2 h / Ambient temperature 3: 30 percent / amalgamated Zn, HCl / aq. ethanol / Heating 4: pyridine / Ambient temperature; 1.) 1 h, -6 - -10 deg C, 2.) 23 deg C, View Scheme | |
Multi-step reaction with 5 steps 1: 95 percent / pyridinium chlorochromate / CH2Cl2 / 2.5 h / Ambient temperature 2: 87.5 percent / acetylation 3: 66 percent / LTBH / tetrahydrofuran / cooling 1 h, r.t., 1 h 4: 30 percent / amalgamated Zn, HCl / aq. ethanol / Heating 5: pyridine / Ambient temperature; 1.) 1 h, -6 - -10 deg C, 2.) 23 deg C, View Scheme |
(25R)-ruscogenin
cholest-5-ene-1α,16β-diol
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 95 percent / pyridinium chlorochromate / CH2Cl2 / 2.5 h / Ambient temperature 2: 70 percent / sodium borohydride / methanol / 2 h / Ambient temperature 3: 30 percent / amalgamated Zn, HCl / aq. ethanol / Heating 4: 1.) p-toluenesulfonyl chloride, 2.) LAH / 1.) pyridine, 1 h, -6 - -10 deg C, 23 deg C, 2.) reflux, 16 h, ether View Scheme | |
Multi-step reaction with 5 steps 1: 95 percent / pyridinium chlorochromate / CH2Cl2 / 2.5 h / Ambient temperature 2: 87.5 percent / acetylation 3: 66 percent / LTBH / tetrahydrofuran / cooling 1 h, r.t., 1 h 4: 30 percent / amalgamated Zn, HCl / aq. ethanol / Heating 5: 1.) p-toluenesulfonyl chloride, 2.) LAH / 1.) pyridine, 1 h, -6 - -10 deg C, 23 deg C, 2.) reflux, 16 h, ether View Scheme |
(25R)-ruscogenin
cholest-5-ene-1α,3β,16β-triol
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 95 percent / pyridinium chlorochromate / CH2Cl2 / 2.5 h / Ambient temperature 2: 70 percent / sodium borohydride / methanol / 2 h / Ambient temperature 3: 30 percent / amalgamated Zn, HCl / aq. ethanol / Heating 4: 1.) p-toluenesulfonyl chloride, 2.) LAH / 1.) pyridine, 1 h, -6 - -10 deg C, 23 deg C, 2.) reflux, 16 h, ether View Scheme | |
Multi-step reaction with 5 steps 1: 95 percent / pyridinium chlorochromate / CH2Cl2 / 2.5 h / Ambient temperature 2: 87.5 percent / acetylation 3: 66 percent / LTBH / tetrahydrofuran / cooling 1 h, r.t., 1 h 4: 30 percent / amalgamated Zn, HCl / aq. ethanol / Heating 5: 1.) p-toluenesulfonyl chloride, 2.) LAH / 1.) pyridine, 1 h, -6 - -10 deg C, 23 deg C, 2.) reflux, 16 h, ether View Scheme |
(25R)-ruscogenin
cholest-5-ene-1α,3β,16β,26-tetrol
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 95 percent / pyridinium chlorochromate / CH2Cl2 / 2.5 h / Ambient temperature 2: 70 percent / sodium borohydride / methanol / 2 h / Ambient temperature 3: 30 percent / amalgamated Zn, HCl / aq. ethanol / Heating View Scheme | |
Multi-step reaction with 4 steps 1: 95 percent / pyridinium chlorochromate / CH2Cl2 / 2.5 h / Ambient temperature 2: 87.5 percent / acetylation 3: 66 percent / LTBH / tetrahydrofuran / cooling 1 h, r.t., 1 h 4: 30 percent / amalgamated Zn, HCl / aq. ethanol / Heating View Scheme |
(25R)-ruscogenin
(20S,22R,25R)-1α,3β-dihydroxyspirost-5-ene
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 95 percent / pyridinium chlorochromate / CH2Cl2 / 2.5 h / Ambient temperature 2: 70 percent / sodium borohydride / methanol / 2 h / Ambient temperature View Scheme | |
Multi-step reaction with 3 steps 1: 95 percent / pyridinium chlorochromate / CH2Cl2 / 2.5 h / Ambient temperature 2: 87.5 percent / acetylation 3: 66 percent / LTBH / tetrahydrofuran / cooling 1 h, r.t., 1 h View Scheme |
(25R)-ruscogenin
1α,16β-diacetoxycholest-5-ene
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 95 percent / pyridinium chlorochromate / CH2Cl2 / 2.5 h / Ambient temperature 2: 70 percent / sodium borohydride / methanol / 2 h / Ambient temperature 3: 30 percent / amalgamated Zn, HCl / aq. ethanol / Heating 4: 1.) p-toluenesulfonyl chloride, 2.) LAH / 1.) pyridine, 1 h, -6 - -10 deg C, 23 deg C, 2.) reflux, 16 h, ether 5: 80 percent View Scheme | |
Multi-step reaction with 6 steps 1: 95 percent / pyridinium chlorochromate / CH2Cl2 / 2.5 h / Ambient temperature 2: 87.5 percent / acetylation 3: 66 percent / LTBH / tetrahydrofuran / cooling 1 h, r.t., 1 h 4: 30 percent / amalgamated Zn, HCl / aq. ethanol / Heating 5: 1.) p-toluenesulfonyl chloride, 2.) LAH / 1.) pyridine, 1 h, -6 - -10 deg C, 23 deg C, 2.) reflux, 16 h, ether 6: 80 percent View Scheme |
(25R)-ruscogenin
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 95 percent / pyridinium chlorochromate / CH2Cl2 / 2.5 h / Ambient temperature 2: 70 percent / sodium borohydride / methanol / 2 h / Ambient temperature 3: 30 percent / amalgamated Zn, HCl / aq. ethanol / Heating 4: pyridine / Ambient temperature; 1.) 1 h, -6 - -10 deg C, 2.) 23 deg C, View Scheme | |
Multi-step reaction with 5 steps 1: 95 percent / pyridinium chlorochromate / CH2Cl2 / 2.5 h / Ambient temperature 2: 87.5 percent / acetylation 3: 66 percent / LTBH / tetrahydrofuran / cooling 1 h, r.t., 1 h 4: 30 percent / amalgamated Zn, HCl / aq. ethanol / Heating 5: pyridine / Ambient temperature; 1.) 1 h, -6 - -10 deg C, 2.) 23 deg C, View Scheme |
(25R)-ruscogenin
1α,3β,16β-triacetoxycholest-5-ene
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 95 percent / pyridinium chlorochromate / CH2Cl2 / 2.5 h / Ambient temperature 2: 70 percent / sodium borohydride / methanol / 2 h / Ambient temperature 3: 30 percent / amalgamated Zn, HCl / aq. ethanol / Heating 4: 1.) p-toluenesulfonyl chloride, 2.) LAH / 1.) pyridine, 1 h, -6 - -10 deg C, 23 deg C, 2.) reflux, 16 h, ether View Scheme | |
Multi-step reaction with 6 steps 1: 95 percent / pyridinium chlorochromate / CH2Cl2 / 2.5 h / Ambient temperature 2: 87.5 percent / acetylation 3: 66 percent / LTBH / tetrahydrofuran / cooling 1 h, r.t., 1 h 4: 30 percent / amalgamated Zn, HCl / aq. ethanol / Heating 5: 1.) p-toluenesulfonyl chloride, 2.) LAH / 1.) pyridine, 1 h, -6 - -10 deg C, 23 deg C, 2.) reflux, 16 h, ether View Scheme |
(25R)-ruscogenin
1α,3β,16β,26-tetraacetoxycholest-5-ene
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 95 percent / pyridinium chlorochromate / CH2Cl2 / 2.5 h / Ambient temperature 2: 70 percent / sodium borohydride / methanol / 2 h / Ambient temperature 3: 30 percent / amalgamated Zn, HCl / aq. ethanol / Heating 4: 87 percent View Scheme | |
Multi-step reaction with 5 steps 1: 95 percent / pyridinium chlorochromate / CH2Cl2 / 2.5 h / Ambient temperature 2: 87.5 percent / acetylation 3: 66 percent / LTBH / tetrahydrofuran / cooling 1 h, r.t., 1 h 4: 30 percent / amalgamated Zn, HCl / aq. ethanol / Heating 5: 87 percent View Scheme |
(25R)-ruscogenin
cholest-5-ene-1β,3β-diol
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 33 percent / amalgamated Zn, HCl / aq. ethanol / 2.5 h / Heating 2: 1.) p-toluenesulfonyl chloride, 2.) LAH / 1.) pyridine, 1 h, -6 - -10 deg C, 23 deg C, 2.) reflux, 16 h, ether 3: 0.158 g / pyridine 4: 0.544 g / pyridine / 0 °C 5: 0.346 g / LAH / diethyl ether / Heating View Scheme |
The CAS register number of Spirost-5-ene-1,3-diol,(1β,3β,25R)- is 472-11-7. It also can be called as 25D-Spirost-5-ene-1β,3β-diol and the systematic name about this chemical is (1β,3β,25R)-spirost-5-en-1,3-diol. The molecular formula about this chemical is C27H42O4 and the molecular weight is 430.62. It belongs to the following product category which includes Miscellaneous Natural Products.
Physical properties about Spirost-5-ene-1,3-diol,(1β,3β,25R)- are: (1)ACD/LogP: 4.29; (2)#H bond acceptors: 4; (3)#H bond donors: 2; (4)#Freely Rotating Bonds: 2; (5)Polar Surface Area: 36.92 Å2; (6)Index of Refraction: 1.576; (7)Molar Refractivity: 120.87 cm3; (8)Molar Volume: 364.7 cm3; (9)Polarizability: 47.91x10-24cm3; (10)Surface Tension: 48.7 dyne/cm; (11)Density: 1.18 g/cm3; (12)Flash Point: 294.3 °C; (13)Enthalpy of Vaporization: 97.24 kJ/mol; (14)Boiling Point: 563.1 °C at 760 mmHg; (15)Vapour Pressure: 5.03E-15 mmHg at 25 °C.
Preparation: this chemical can be prepared by (25R)-Ruscogenin. This reaction will need reagent of chromium (VI)-oxide, aqueous acetic acid.
Uses of Spirost-5-ene-1,3-diol,(1β,3β,25R)-: it can be used to produce epiruscogenin and (25R)-Ruscogenin. This reaction will need reagent of lithium aluminum tri-t-butoxyhydride and solvent of tetrahydrofuran. The reaction needs 1 hour of cooling and 1 hour of r.t.. The yield is about 40%.
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(=C/C[C@H]3[C@@H]5C4)\C[C@@H](O)C[C@H]6O)C
(2)InChI: InChI=1/C27H42O4/c1-15-7-10-27(30-14-15)16(2)24-22(31-27)13-21-19-6-5-17-11-18(28)12-23(29)26(17,4)20(19)8-9-25(21,24)3/h5,15-16,18-24,28-29H,6-14H2,1-4H3/t15-,16+,18-,19-,20+,21+,22+,23-,24+,25+,26+,27-/m1/s1
(3)InChIKey: QMQIQBOGXYYATH-IDABPMKMBV
(4)Std. InChI: InChI=1S/C27H42O4/c1-15-7-10-27(30-14-15)16(2)24-22(31-27)13-21-19-6-5-17-11-18(28)12-23(29)26(17,4)20(19)8-9-25(21,24)3/h5,15-16,18-24,28-29H,6-14H2,1-4H3/t15-,16+,18-,19-,20+,21+,22+,23-,24+,25+,26+,27-/m1/s1
(5)Std. InChIKey: QMQIQBOGXYYATH-IDABPMKMSA-N
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