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Calcipotriol
Cas No: 112965-21-6
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Calcipotriol
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Manufacture Calcipotriol or Calcipotriene and intermediates
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High Quality 99% Calcipotriene 112965-21-6 GMP manufacturer
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Calcipotriene
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112965-21-6 Usage

Chemical Properties

White Crystalline Solid

Pharmacology

Calcipotriene (Dovonex) enhances the effectiveness of ultraviolet B (UVB) but also increases photosensitivity in UVB-treated patients. Ultraviolet light, 6% salicylic acid, 12% lactic acid, hydrocortisone valerate 0.2% ointment, and tazarotene (Tazorac) gel degrade calcipotriene (Dovonex). Halobetasol ointment and 5% tar gel are compatible with Calcipotriene (Dovonex). A British study found calcipotriene (Dovonex) to be safe and effective in a pediatric population over the age of 3, although it is not approved by the FDA.

Uses

antipsoriatic;viamin D receptor (VDR) affinity

Uses

An antipsoriatic. A vitamin D3 analogue with low calcemic activity

Uses

A labelled antipsoriatic. A vitamin D3 analogue with low calcemic activity.

Therapeutic Function

Antipsoriatic

Manufacturing Process

(1S,3R)-Bis-(t-butyldimethylsilyloxy)-(20S)-formyl-9,10-secopregna(5E,7E,10 (19))triene (Calverley Tetrahedron 43.4609 (1967) and (cyclopropyl)(tri-phenylphoshoranylidene)ketone are stirred in dimethyl sulfoxide under nitrogen. The reaction mixture is then diluted at room temperature with ethyl acetate and washed with common salt solution. The organic phase is dried on sodium sulfate and filtered. After removal of the solvent, the residue is filtered with toluene through silica gel. Evaporation of the solvent and gradient chromatography (toluene/hexane (1:1)-toluene) of the residue on silica gel yield (5E,7E,22E),(1S,3R)-1,3-bis-(t-butyldimethylsilyloxy)-24-cyclopropyl- 9,10-secochola-5,7,10(19),22-tetraene-24-one.(5E,7E,22E),(1S,3R)-1,3-Bis-(t-butyldimethylsilyloxy)-24-cyclopropyl-9,10- secochola-5,7,10(19),22-tetraene-24-one in tetrahydrofuran and methanol are mixed with a 0.4 M methanol CeCl3·7H2O solution. Sodium borohydride is added by portions under nitrogen with ice cooling. The suspension is stirred with ice cooling and then put into ice/common salt solution. The aqueous phase is extracted with ethyl acetate, the organic phase is washed neutral with water and dried on sodium sulfate. Filtration and removal of the solvent yield oil. By chromatography on silica gel with ethyl acetate/hexane (1:9). The (5E,7E,22E),(1S,3R,24S)-1,3-bis-(t-butyldimethylsilyloxy)-24-cyclopropyl- 9,10-secochola-5,7,10(19),22-tetraene-24-ol is obtained.(5E,7E,22E),(1S,3R,24S)-1,3-Bis-(t-butyldimethylsilyloxy)-24-cyclopropyl- 9,10-secochola-5,7,10(19),22-tetraene-24-ol is dissolved in toluene and after addition of anthracene and 1 drop of triethylamine it is radiated at room temperature with a high pressure mercury vapor lamp (Heraeus TQ 150) through Pyrex glass. The reaction mixture is concentrated by evaporation and the residue a mixture of (5Z,7E,22E),(1S,3R,24S)-1,3-bis-(t-butyldimethylsilyloxy)-24-cyclopropyl-9,10-secochola-5,7,10(19),22-tetraene- 24-ol and anthracene - is directly reacted with tetrabutylammonium fluoride.(5Z,7E,22E),(1S,3R,24S)-1,3-Bis-(t-butyldimethylsilyloxy)-24-cyclopropyl- 9,10-secochola-5,7,10(19),22-tetraene-24-ol in tetrahydrofuran is kept with a 1 M solution of tetrabutylammonium fluoride in tetrahydrofuran under nitrogen. For working up, the cooled reaction mixture is poured into cold sodium bicarbonate solution and then extracted with ethyl acetate. After drying of the organic phase on sodium sulfate, filtration and evaporation of the solvent yields a resin-like residue. Chromatography on silica gel with ethyl acetate/hexane (2:1) yields (5Z,7E,22E),(1S,3R,24S)-24-cyclopropyl-9,10- secochola-5,7,10(19),22-tetraene-1,3,24-triol.

Brand name

Dovonex (Leo);Daivonex.

Indications

Calcipotriene (Dovonex), a synthetic vitamin D3 derivative, is indicated for the treatment of moderate plaque psoriasis. Its mechanism of action is unknown, although it competes for calcitriol receptors on keratinocytes and normalizes differentiation. It also has a variety of immunomodulatory effects in the skin. Although the drug can cause local irritation, the most serious toxicities are hypercalciuria and hypercalcemia, which are usually reversible.

Originator

Leo Denmark (Denmark)

Biological Activity

Vitamin D 3 analog that displays minimal effects on calcium homeostasis. Regulates cell differentiation and proliferation; exhibits antiproliferative activity against human HL-60, HL60/MX2, MCF-7, T47D, SCC-25 and mouse WEHI-3 cancer cell lines.

Description

Calcipotriol is a topical vitaminD3 derivative effective in the treatment of psoriasis vulgaris. The drug acts by binding to vitamin D3 receptors in the skin keratinocytes, producing an elevation in cell differentiation and a reduction in cell proliferation. Although its efficacy is comparable to calcitriol, calcipotriol exhibits at least 100 times less effect on calcium metabolism in rats.
InChI:InChI=1/C27H40O3/c1-17(6-13-25(29)20-8-9-20)23-11-12-24-19(5-4-14-27(23,24)3)7-10-21-15-22(28)16-26(30)18(21)2/h6-7,10,13,17,20,22-26,28-30H,2,4-5,8-9,11-12,14-16H2,1,3H3/b13-6+,19-7+,21-10-/t17-,22-,23-,24?,25-,26+,27-/m1/s1

112965-21-6 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
USP (1086141)  Calcipotriene  United States Pharmacopeia (USP) Reference Standard 112965-21-6 1086141-200MG 29,398.59CNY Detail
Sigma (C4369)  Calcipotriol hydrate  ≥98% (HPLC) 112965-21-6 C4369-10MG 1,960.92CNY Detail
Sigma (C4369)  Calcipotriol hydrate  ≥98% (HPLC) 112965-21-6 C4369-50MG 7,593.30CNY Detail

112965-21-6SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name calcipotriol

1.2 Other means of identification

Product number -
Other names 25-HYDROXYCHOLECALCIFEROL

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:112965-21-6 SDS

112965-21-6Synthetic route

(1S,3R)-bis(tert-butyldimethylsilyloxy)-20(R)-(3'(S)-cyclopropyl-3'-hydroxyprop-1'(E)-enyl)-9,10-secopregna-5(Z),7(E),10(19)-triene
112875-61-3

(1S,3R)-bis(tert-butyldimethylsilyloxy)-20(R)-(3'(S)-cyclopropyl-3'-hydroxyprop-1'(E)-enyl)-9,10-secopregna-5(Z),7(E),10(19)-triene

calcipotriene
112965-21-6

calcipotriene

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃;87%
With tetrabutyl ammonium fluoride In tetrahydrofuran at 60℃; for 0.833333h;73%
With tetrabutyl ammonium fluoride In tetrahydrofuran at 40℃; for 2h;
With tetrabutyl ammonium fluoride In tetrahydrofuran at 60℃;
Stage #1: (1S,3R)-bis(tert-butyldimethylsilyloxy)-20(R)-(3'(S)-cyclopropyl-3'-hydroxyprop-1'(E)-enyl)-9,10-secopregna-5(Z),7(E),10(19)-triene With tetrabutyl ammonium fluoride In tetrahydrofuran at 60 - 65℃; for 2h;
Stage #2: With water; sodium hydrogencarbonate In tetrahydrofuran; ethyl acetate for 0.25h;
Cyclopropyl methyl ketone
765-43-5

Cyclopropyl methyl ketone

calcipotriene
112965-21-6

calcipotriene

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: 87 percent / bromine / methanol / 0.5 h / Ambient temperature
2: 84 percent
3: 86 percent / 2N sodium hydroxide / H2O; CH2Cl2
5: N-methylmorpholine N-oxide, selenium dioxide
6: imidazole / dimethylformamide
7: 33 percent / NaBH4, CeCl3*6H2O / methanol / further reag.: (S)-BINAL-H
8: anthracene, triethylamine / toluene / 1 h / 20 °C / Irradiation
9: 73 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.83 h / 60 °C
View Scheme
Multi-step reaction with 7 steps
1: 87 percent / bromine / methanol / 0.5 h / Ambient temperature
2: 84 percent
3: 86 percent / 2N sodium hydroxide / H2O; CH2Cl2
4: dimethylsulfoxide / 4 h / 105 °C
5: 33 percent / NaBH4, CeCl3*6H2O / methanol / further reag.: (S)-BINAL-H
6: anthracene, triethylamine / toluene / 1 h / 20 °C / Irradiation
7: 73 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.83 h / 60 °C
View Scheme
2-bromo-1-cyclopropylethan-1-one
69267-75-0

2-bromo-1-cyclopropylethan-1-one

calcipotriene
112965-21-6

calcipotriene

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: 84 percent
2: 86 percent / 2N sodium hydroxide / H2O; CH2Cl2
4: N-methylmorpholine N-oxide, selenium dioxide
5: imidazole / dimethylformamide
6: 33 percent / NaBH4, CeCl3*6H2O / methanol / further reag.: (S)-BINAL-H
7: anthracene, triethylamine / toluene / 1 h / 20 °C / Irradiation
8: 73 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.83 h / 60 °C
View Scheme
Multi-step reaction with 6 steps
1: 84 percent
2: 86 percent / 2N sodium hydroxide / H2O; CH2Cl2
3: dimethylsulfoxide / 4 h / 105 °C
4: 33 percent / NaBH4, CeCl3*6H2O / methanol / further reag.: (S)-BINAL-H
5: anthracene, triethylamine / toluene / 1 h / 20 °C / Irradiation
6: 73 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.83 h / 60 °C
View Scheme
1-cyclopropyl-2-(triphenyl-λ5-phosphanylidene)ethan-1-one
7691-76-1

1-cyclopropyl-2-(triphenyl-λ5-phosphanylidene)ethan-1-one

calcipotriene
112965-21-6

calcipotriene

Conditions
ConditionsYield
Multi-step reaction with 6 steps
2: N-methylmorpholine N-oxide, selenium dioxide
3: imidazole / dimethylformamide
4: 33 percent / NaBH4, CeCl3*6H2O / methanol / further reag.: (S)-BINAL-H
5: anthracene, triethylamine / toluene / 1 h / 20 °C / Irradiation
6: 73 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.83 h / 60 °C
View Scheme
Multi-step reaction with 4 steps
1: dimethylsulfoxide / 4 h / 105 °C
2: 33 percent / NaBH4, CeCl3*6H2O / methanol / further reag.: (S)-BINAL-H
3: anthracene, triethylamine / toluene / 1 h / 20 °C / Irradiation
4: 73 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.83 h / 60 °C
View Scheme
3(R)-(tert-butyldimethylsilyloxy)-20(S)-formyl-9,10-secopregna-5(Z),7(E),10(19)-triene
112828-12-3

3(R)-(tert-butyldimethylsilyloxy)-20(S)-formyl-9,10-secopregna-5(Z),7(E),10(19)-triene

calcipotriene
112965-21-6

calcipotriene

Conditions
ConditionsYield
Multi-step reaction with 6 steps
2: N-methylmorpholine N-oxide, selenium dioxide
3: imidazole / dimethylformamide
4: 33 percent / NaBH4, CeCl3*6H2O / methanol / further reag.: (S)-BINAL-H
5: anthracene, triethylamine / toluene / 1 h / 20 °C / Irradiation
6: 73 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.83 h / 60 °C
View Scheme
(S)-3-[(1R,3aS,7aR)-7a-Methyl-1-((E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl)-octahydro-inden-(4E)-ylidenemethyl]-2,2-dioxo-2,3,4,5,6,7-hexahydro-1H-2λ6-benzo[c]thiophen-5-ol
87680-65-7

(S)-3-[(1R,3aS,7aR)-7a-Methyl-1-((E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl)-octahydro-inden-(4E)-ylidenemethyl]-2,2-dioxo-2,3,4,5,6,7-hexahydro-1H-2λ6-benzo[c]thiophen-5-ol

calcipotriene
112965-21-6

calcipotriene

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: 42 percent / imidazole / dimethylformamide / 1.5 h / 20 °C
2: 1.) ozone 2.) PPh3 / 1.) CH2Cl2, MeOH, -60 deg C 2.) CH2Cl2, MeOH, -60 to 0 deg C
3: NaHCO3 / aq. ethanol / Heating
5: N-methylmorpholine N-oxide, selenium dioxide
6: imidazole / dimethylformamide
7: 33 percent / NaBH4, CeCl3*6H2O / methanol / further reag.: (S)-BINAL-H
8: anthracene, triethylamine / toluene / 1 h / 20 °C / Irradiation
9: 73 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.83 h / 60 °C
View Scheme
Multi-step reaction with 9 steps
1: 52 percent / imidazole / dimethylformamide / 1.5 h / 20 °C
2: 1.) ozone 2.) PPh3 / 1.) CH2Cl2, MeOH, -60 deg C 2.) CH2Cl2, MeOH, -60 to 0 deg C
3: NaHCO3 / aq. ethanol / Heating
5: N-methylmorpholine N-oxide, selenium dioxide
6: imidazole / dimethylformamide
7: 33 percent / NaBH4, CeCl3*6H2O / methanol / further reag.: (S)-BINAL-H
8: anthracene, triethylamine / toluene / 1 h / 20 °C / Irradiation
9: 73 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.83 h / 60 °C
View Scheme
20(R),3(R)-(tert-butyldimethylsilyloxy)-20-(3'-cyclopropyl-3'-oxoprop-1'(E)-enyl)-9,10-secopregna-5(Z),7(E),10(19)-triene
112849-18-0

20(R),3(R)-(tert-butyldimethylsilyloxy)-20-(3'-cyclopropyl-3'-oxoprop-1'(E)-enyl)-9,10-secopregna-5(Z),7(E),10(19)-triene

calcipotriene
112965-21-6

calcipotriene

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: N-methylmorpholine N-oxide, selenium dioxide
2: imidazole / dimethylformamide
3: 33 percent / NaBH4, CeCl3*6H2O / methanol / further reag.: (S)-BINAL-H
4: anthracene, triethylamine / toluene / 1 h / 20 °C / Irradiation
5: 73 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.83 h / 60 °C
View Scheme
(E)-(R)-4-{(1R,3aS,7aR)-4-[2-[(R)-5-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-2-methylene-cyclohex-(E)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-1-cyclopropyl-pent-2-en-1-one

(E)-(R)-4-{(1R,3aS,7aR)-4-[2-[(R)-5-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-2-methylene-cyclohex-(E)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-1-cyclopropyl-pent-2-en-1-one

calcipotriene
112965-21-6

calcipotriene

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: imidazole / dimethylformamide
2: 33 percent / NaBH4, CeCl3*6H2O / methanol / further reag.: (S)-BINAL-H
3: anthracene, triethylamine / toluene / 1 h / 20 °C / Irradiation
4: 73 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.83 h / 60 °C
View Scheme
(2-cyclopropyl-2-oxoethyl) (triphenyl)phosphonium bromide
112849-15-7

(2-cyclopropyl-2-oxoethyl) (triphenyl)phosphonium bromide

calcipotriene
112965-21-6

calcipotriene

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 86 percent / 2N sodium hydroxide / H2O; CH2Cl2
3: N-methylmorpholine N-oxide, selenium dioxide
4: imidazole / dimethylformamide
5: 33 percent / NaBH4, CeCl3*6H2O / methanol / further reag.: (S)-BINAL-H
6: anthracene, triethylamine / toluene / 1 h / 20 °C / Irradiation
7: 73 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.83 h / 60 °C
View Scheme
Multi-step reaction with 5 steps
1: 86 percent / 2N sodium hydroxide / H2O; CH2Cl2
2: dimethylsulfoxide / 4 h / 105 °C
3: 33 percent / NaBH4, CeCl3*6H2O / methanol / further reag.: (S)-BINAL-H
4: anthracene, triethylamine / toluene / 1 h / 20 °C / Irradiation
5: 73 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.83 h / 60 °C
View Scheme
(7Z)-Vitamin D2
247900-07-8

(7Z)-Vitamin D2

calcipotriene
112965-21-6

calcipotriene

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1: liq. SO2 / 0.5 h / Heating
2: 42 percent / imidazole / dimethylformamide / 1.5 h / 20 °C
3: 1.) ozone 2.) PPh3 / 1.) CH2Cl2, MeOH, -60 deg C 2.) CH2Cl2, MeOH, -60 to 0 deg C
4: NaHCO3 / aq. ethanol / Heating
6: N-methylmorpholine N-oxide, selenium dioxide
7: imidazole / dimethylformamide
8: 33 percent / NaBH4, CeCl3*6H2O / methanol / further reag.: (S)-BINAL-H
9: anthracene, triethylamine / toluene / 1 h / 20 °C / Irradiation
10: 73 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.83 h / 60 °C
View Scheme
Multi-step reaction with 10 steps
1: liq. SO2 / 0.5 h / Heating
2: 52 percent / imidazole / dimethylformamide / 1.5 h / 20 °C
3: 1.) ozone 2.) PPh3 / 1.) CH2Cl2, MeOH, -60 deg C 2.) CH2Cl2, MeOH, -60 to 0 deg C
4: NaHCO3 / aq. ethanol / Heating
6: N-methylmorpholine N-oxide, selenium dioxide
7: imidazole / dimethylformamide
8: 33 percent / NaBH4, CeCl3*6H2O / methanol / further reag.: (S)-BINAL-H
9: anthracene, triethylamine / toluene / 1 h / 20 °C / Irradiation
10: 73 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.83 h / 60 °C
View Scheme
3(S)-tert-butyldimethylsilyloxy-20(S)-formyl-9,10-secoprega-5,7(E),10(19)-triene
87407-47-4

3(S)-tert-butyldimethylsilyloxy-20(S)-formyl-9,10-secoprega-5,7(E),10(19)-triene

calcipotriene
112965-21-6

calcipotriene

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: NaHCO3 / aq. ethanol / Heating
3: N-methylmorpholine N-oxide, selenium dioxide
4: imidazole / dimethylformamide
5: 33 percent / NaBH4, CeCl3*6H2O / methanol / further reag.: (S)-BINAL-H
6: anthracene, triethylamine / toluene / 1 h / 20 °C / Irradiation
7: 73 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.83 h / 60 °C
View Scheme
3(S)-tert-butyldimethylsilyloxy-20(S)-formyl-9,10-secoprega-5,7(E),10(19)-triene
87422-13-7

3(S)-tert-butyldimethylsilyloxy-20(S)-formyl-9,10-secoprega-5,7(E),10(19)-triene

calcipotriene
112965-21-6

calcipotriene

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: NaHCO3 / aq. ethanol / Heating
3: N-methylmorpholine N-oxide, selenium dioxide
4: imidazole / dimethylformamide
5: 33 percent / NaBH4, CeCl3*6H2O / methanol / further reag.: (S)-BINAL-H
6: anthracene, triethylamine / toluene / 1 h / 20 °C / Irradiation
7: 73 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.83 h / 60 °C
View Scheme
(3S,6R)-(tert-butyldimethylsilyloxy)-9,10-seco-ergosta-5,7(E),10(19),22(E)-tetraene SO2 adduct
87417-26-3

(3S,6R)-(tert-butyldimethylsilyloxy)-9,10-seco-ergosta-5,7(E),10(19),22(E)-tetraene SO2 adduct

calcipotriene
112965-21-6

calcipotriene

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: 1.) ozone 2.) PPh3 / 1.) CH2Cl2, MeOH, -60 deg C 2.) CH2Cl2, MeOH, -60 to 0 deg C
2: NaHCO3 / aq. ethanol / Heating
4: N-methylmorpholine N-oxide, selenium dioxide
5: imidazole / dimethylformamide
6: 33 percent / NaBH4, CeCl3*6H2O / methanol / further reag.: (S)-BINAL-H
7: anthracene, triethylamine / toluene / 1 h / 20 °C / Irradiation
8: 73 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.83 h / 60 °C
View Scheme
(3S,6S)-(tert-butyldimethylsilyloxy)-9,10-seco-ergosta-5,7(E),10(19),22(E)-tetraene SO2-adduct
87417-26-3, 87417-27-4

(3S,6S)-(tert-butyldimethylsilyloxy)-9,10-seco-ergosta-5,7(E),10(19),22(E)-tetraene SO2-adduct

calcipotriene
112965-21-6

calcipotriene

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: 1.) ozone 2.) PPh3 / 1.) CH2Cl2, MeOH, -60 deg C 2.) CH2Cl2, MeOH, -60 to 0 deg C
2: NaHCO3 / aq. ethanol / Heating
4: N-methylmorpholine N-oxide, selenium dioxide
5: imidazole / dimethylformamide
6: 33 percent / NaBH4, CeCl3*6H2O / methanol / further reag.: (S)-BINAL-H
7: anthracene, triethylamine / toluene / 1 h / 20 °C / Irradiation
8: 73 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.83 h / 60 °C
View Scheme
(1S,3R,3'S)-bis(tert-butyldimethylsilyloxy)-20(R)-(3'-cyclopropyl-3'-hydroxyprop-1'(E)-enyl)-9,10-secopregna-5(E),7(E),10(19)-triene
112849-27-1

(1S,3R,3'S)-bis(tert-butyldimethylsilyloxy)-20(R)-(3'-cyclopropyl-3'-hydroxyprop-1'(E)-enyl)-9,10-secopregna-5(E),7(E),10(19)-triene

calcipotriene
112965-21-6

calcipotriene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: anthracene, triethylamine / toluene / 1 h / 20 °C / Irradiation
2: 73 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.83 h / 60 °C
View Scheme
1(S),3(R)-bis(tert-butyldimethylsilyloxy)-20(R)-(3’-cyclopropyl-3’-oxypropyl-1’(E)-enyl)-9,10-secopregna-5(E),7(E),10(19)-triene
112849-17-9

1(S),3(R)-bis(tert-butyldimethylsilyloxy)-20(R)-(3’-cyclopropyl-3’-oxypropyl-1’(E)-enyl)-9,10-secopregna-5(E),7(E),10(19)-triene

calcipotriene
112965-21-6

calcipotriene

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 33 percent / NaBH4, CeCl3*6H2O / methanol / further reag.: (S)-BINAL-H
2: anthracene, triethylamine / toluene / 1 h / 20 °C / Irradiation
3: 73 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.83 h / 60 °C
View Scheme
(5Z,7E,22E)-(1S,3R,24R)-24-acetoxy-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3-diol

(5Z,7E,22E)-(1S,3R,24R)-24-acetoxy-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3-diol

A

20(R)-(3'(R)-cyclopropyl-3'-hydroxyprop-1'(E)-enyl)-1(S),3(R)-dihydroxy-9,10-secopregna-5(Z),7(E),10(19)-triene
112827-99-3

20(R)-(3'(R)-cyclopropyl-3'-hydroxyprop-1'(E)-enyl)-1(S),3(R)-dihydroxy-9,10-secopregna-5(Z),7(E),10(19)-triene

B

calcipotriene
112965-21-6

calcipotriene

Conditions
ConditionsYield
With silica gel In hexane; dichloromethane for 24h; Product distribution / selectivity;
PRI-2201

PRI-2201

phenylboronic acid
98-80-6

phenylboronic acid

A

C33H43BO3
934338-46-2

C33H43BO3

B

calcipotriene
112965-21-6

calcipotriene

Conditions
ConditionsYield
In acetone for 3h; Purification / work up;
PRI-2205
113082-99-8

PRI-2205

calcipotriene
112965-21-6

calcipotriene

Conditions
ConditionsYield
With 9-acetylanthracene In acetone at 10℃; Product distribution / selectivity; UV-irradiation;
C27H40O3
934338-38-2

C27H40O3

A

(5Z,7E,22E,24R)-24-cyclopropyl-9,10-secochola-5,7,10(19),22-tetraene-1β,3β,24-triol

(5Z,7E,22E,24R)-24-cyclopropyl-9,10-secochola-5,7,10(19),22-tetraene-1β,3β,24-triol

B

calcipotriene
112965-21-6

calcipotriene

Conditions
ConditionsYield
With 9-acetylanthracene In acetone at 10℃; Product distribution / selectivity; UV-irradiation;
C35H60O2Si2
590366-68-0

C35H60O2Si2

calcipotriene
112965-21-6

calcipotriene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: bis(cyclohexanyl)borane; diethylzinc; (2R)-3-exo-(dimethylamino)isoborneol / hexane / -20 - 0 °C
1.2: 0 °C
2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C
View Scheme
[(2Z)-2-[(3S,5R)-3,5-bis(tert-butyldimethylsilanyloxy)-2-methylenecyclohexylidene]ethyl]diphenylphosphine oxide
81522-68-1

[(2Z)-2-[(3S,5R)-3,5-bis(tert-butyldimethylsilanyloxy)-2-methylenecyclohexylidene]ethyl]diphenylphosphine oxide

calcipotriene
112965-21-6

calcipotriene

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: n-hexyllithium / -78 °C
2.1: bis(cyclohexanyl)borane; diethylzinc; (2R)-3-exo-(dimethylamino)isoborneol / hexane / -20 - 0 °C
2.2: 0 °C
3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C
View Scheme
tert-butyl[(1S)-1-cyclopropyl-2-[(R)-4-methylbenzenesulfinyl]ethoxy]dimethylsilane

tert-butyl[(1S)-1-cyclopropyl-2-[(R)-4-methylbenzenesulfinyl]ethoxy]dimethylsilane

calcipotriene
112965-21-6

calcipotriene

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: 2,4,6-trimethyl-pyridine; trifluoroacetic anhydride / acetonitrile / 0.17 h / 30 °C / Inert atmosphere
1.2: 0.08 h
2.1: dichloromethane / 0.17 h / -50 °C / Inert atmosphere
3.1: N-ethyl-N,N-diisopropylamine / water; acetonitrile
4.1: hexaammonium heptamolybdate tetrahydrate; dihydrogen peroxide / isopropyl alcohol / 20 - 30 °C
5.1: potassium hexamethylsilazane / tetrahydrofuran / 2 h / -50 °C / Inert atmosphere
6.1: triethylamine; anthracene / toluene / 1.5 h / 20 °C / UV-irradiation
6.2: 1 h / 60 °C
View Scheme
Multi-step reaction with 6 steps
1.1: 2,4,6-trimethyl-pyridine; trifluoroacetic anhydride / acetonitrile / 0.17 h / 30 °C / Inert atmosphere
1.2: 0.08 h
2.1: dichloromethane / 0.17 h / -50 °C / Inert atmosphere
3.1: lithium diisopropyl amide / tetrahydrofuran; N,N-dimethyl-formamide / 0.08 h
3.2: 2 h / 30 °C
4.1: 3-chloro-benzenecarboperoxoic acid / acetonitrile / 0 - 20 °C
5.1: lithium diisopropyl amide / tetrahydrofuran / 2 h / -30 °C / Inert atmosphere
6.1: triethylamine; anthracene / toluene / 1.5 h / 20 °C / UV-irradiation
6.2: 1 h / 60 °C
View Scheme
(1S,2R)-1-cyclopropyl-2-(p-tolylsulfoxy)-O-methoxy methyl ether

(1S,2R)-1-cyclopropyl-2-(p-tolylsulfoxy)-O-methoxy methyl ether

calcipotriene
112965-21-6

calcipotriene

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: potassium carbonate; acetic anhydride / acetonitrile / 0.5 h / 50 °C / Inert atmosphere
1.2: 0.17 h
2.1: triethylamine / acetonitrile / 0.5 h / 0 °C / Inert atmosphere
3.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.08 h / Inert atmosphere
3.2: 2 h / 30 °C
4.1: 3-chloro-benzenecarboperoxoic acid / acetonitrile / 0 - 20 °C
5.1: sodium hexamethyldisilazane / diethyl ether / 3 h / -80 °C / Inert atmosphere
6.1: triethylamine; anthracene / toluene / 1.5 h / UV-irradiation
6.2: 1 h / 60 °C
6.3: 3 h / 20 °C
View Scheme
(S)-2-{[(benzyloxy)carbonyl]oxy}-2-cyclopropylethan-1-ol

(S)-2-{[(benzyloxy)carbonyl]oxy}-2-cyclopropylethan-1-ol

calcipotriene
112965-21-6

calcipotriene

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / -30 °C / Inert atmosphere
2.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C
3.1: 3-chloro-benzenecarboperoxoic acid / acetonitrile / 2 h / 20 - 50 °C
4.1: lithium hexamethyldisilazane / tetrahydrofuran; 1,4-dioxane / 2 h / -20 °C / Inert atmosphere
5.1: triethylamine; anthracene / toluene / 1.5 h / UV-irradiation
5.2: 1 h / 60 °C
5.3: 3 h / 20 °C / 760.05 Torr
View Scheme
(S)-2-[(tert-butyldimethylsilyl)oxy]-2-cyclopropylethan-1-ol

(S)-2-[(tert-butyldimethylsilyl)oxy]-2-cyclopropylethan-1-ol

calcipotriene
112965-21-6

calcipotriene

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: dichloromethane / 0.17 h / -50 °C / Inert atmosphere
2.1: N-ethyl-N,N-diisopropylamine / water; acetonitrile
3.1: hexaammonium heptamolybdate tetrahydrate; dihydrogen peroxide / isopropyl alcohol / 20 - 30 °C
4.1: potassium hexamethylsilazane / tetrahydrofuran / 2 h / -50 °C / Inert atmosphere
5.1: triethylamine; anthracene / toluene / 1.5 h / 20 °C / UV-irradiation
5.2: 1 h / 60 °C
View Scheme
Multi-step reaction with 5 steps
1.1: dichloromethane / 0.17 h / -50 °C / Inert atmosphere
2.1: lithium diisopropyl amide / tetrahydrofuran; N,N-dimethyl-formamide / 0.08 h
2.2: 2 h / 30 °C
3.1: 3-chloro-benzenecarboperoxoic acid / acetonitrile / 0 - 20 °C
4.1: lithium diisopropyl amide / tetrahydrofuran / 2 h / -30 °C / Inert atmosphere
5.1: triethylamine; anthracene / toluene / 1.5 h / 20 °C / UV-irradiation
5.2: 1 h / 60 °C
View Scheme
(S)-2-cyclopropyl-2-(methoxymethoxy)ethan-1-ol

(S)-2-cyclopropyl-2-(methoxymethoxy)ethan-1-ol

calcipotriene
112965-21-6

calcipotriene

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: triethylamine / acetonitrile / 0.5 h / 0 °C / Inert atmosphere
2.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.08 h / Inert atmosphere
2.2: 2 h / 30 °C
3.1: 3-chloro-benzenecarboperoxoic acid / acetonitrile / 0 - 20 °C
4.1: sodium hexamethyldisilazane / diethyl ether / 3 h / -80 °C / Inert atmosphere
5.1: triethylamine; anthracene / toluene / 1.5 h / UV-irradiation
5.2: 1 h / 60 °C
5.3: 3 h / 20 °C
View Scheme
(1S)-2-{[(benzyloxy)carbonyl]oxy}-2-cyclopropylethyl trifluoromethanesulfonate

(1S)-2-{[(benzyloxy)carbonyl]oxy}-2-cyclopropylethyl trifluoromethanesulfonate

calcipotriene
112965-21-6

calcipotriene

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C
2.1: 3-chloro-benzenecarboperoxoic acid / acetonitrile / 2 h / 20 - 50 °C
3.1: lithium hexamethyldisilazane / tetrahydrofuran; 1,4-dioxane / 2 h / -20 °C / Inert atmosphere
4.1: triethylamine; anthracene / toluene / 1.5 h / UV-irradiation
4.2: 1 h / 60 °C
4.3: 3 h / 20 °C / 760.05 Torr
View Scheme
all-cis-6,9,12-octadecatrienoic acid
506-26-3

all-cis-6,9,12-octadecatrienoic acid

calcipotriene
112965-21-6

calcipotriene

A

calcipotriol 24-γ-linolenoate

calcipotriol 24-γ-linolenoate

B

calcipotriol bis(γ-linolenoate)

calcipotriol bis(γ-linolenoate)

Conditions
ConditionsYield
With 4-(dimethylamino)pypiridine; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 3h;
(9Z,12Z,15Z)-octadeca-9-12,15-trienoic acid
463-40-1

(9Z,12Z,15Z)-octadeca-9-12,15-trienoic acid

calcipotriene
112965-21-6

calcipotriene

A

calcipotriol 24-linolenoate

calcipotriol 24-linolenoate

B

calcipotriol dilinolenoate

calcipotriol dilinolenoate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 3h;
(9Z,12Z,15Z)-octadeca-9-12,15-trienoic acid
463-40-1

(9Z,12Z,15Z)-octadeca-9-12,15-trienoic acid

calcipotriene
112965-21-6

calcipotriene

calcipotriol mono-linoleic ester

calcipotriol mono-linoleic ester

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 3h;
calcipotriene
112965-21-6

calcipotriene

calcipotriol monohydrate

calcipotriol monohydrate

Conditions
ConditionsYield
With water In ethyl acetate
With ammonia; water at 25 - 40℃; for 12 - 50h; pH=> 7; Product distribution / selectivity;
calcipotriene
112965-21-6

calcipotriene

calci-dioxole
1201658-10-7

calci-dioxole

Conditions
ConditionsYield
With oxygen; methylene blue In methanol at 20℃; Photolysis;
calcipotriene
112965-21-6

calcipotriene

calci-Cl

calci-Cl

Conditions
ConditionsYield
With hydrogenchloride; oxygen In ethanol at 20℃;

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