Product Name

  • Name

    Calcipotriene

  • EINECS 601-218-4
  • CAS No. 112965-21-6
  • Article Data10
  • CAS DataBase
  • Density 1.12 g/cm3
  • Solubility
  • Melting Point 166-168 ºC
  • Formula C27H40O3
  • Boiling Point 582 ºC at 760 mmHg
  • Molecular Weight 412.613
  • Flash Point 250.6 ºC
  • Transport Information
  • Appearance white crystalline solid
  • Safety 26
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 112965-21-6 (Calcipotriene)
  • Hazard Symbols Xi
  • Synonyms 9,10-Secochola-5,7,10(19),22-tetraene-1,3,24-triol,24-cyclopropyl-, (1a,3b,5Z,7E,22E,24S)- (9CI);Calciptriol;Daivonex;Dovonex;MC 903;PRI 2201;Psorcutan;
  • PSA 60.69000
  • LogP 5.09060

Synthetic 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;
...Expand
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;
...Expand
(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;
...Expand
(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℃;

Calcipotriene Specification

The Calcipotriene, with the CAS registry number 112965-21-6, is also known as (1S,3S,5Z)-5-[(2E)-2-[(1R,3aR,7aR)-1-[(E,2S)-5-Cyclopropyl-5-hydroxy-pent-3-en-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidene-cyclohexane-1,3-diol.It belongs to the product categories of Intermediates & Fine Chemicals;Pharmaceuticals;Isotope Labelled Compounds.This chemical's molecular formula is C27H40O3  and molecular weight is 412.61. What's more,Its systematic name is Calcipotriol.It is a topical dermatologic for the treatment of moderate plaque psoriasis. It is White Crystalline Solid.

Physical properties about Calcipotriene are:(1)ACD/LogP: 5.018; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 5.02; (4)ACD/LogD (pH 7.4): 5.02; (5)ACD/BCF (pH 5.5): 3834.42; (6)ACD/BCF (pH 7.4): 3834.42; (7)ACD/KOC (pH 5.5): 12788.11; (8)ACD/KOC (pH 7.4): 12788.11; (9)#H bond acceptors: 3; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 8; (12)Index of Refraction: 1.579; (13)Molar Refractivity: 122.172 cm3; (14)Molar Volume: 367.238 cm3; (15)Surface Tension: 48.1889991760254 dyne/cm; (16)Density: 1.124 g/cm3; (17)Flash Point: 250.613 °C; (18)Enthalpy of Vaporization: 99.905 kJ/mol; (19)Boiling Point: 581.963 °C at 760 mmHg; (20)Vapour Pressure: 0 mmHg at 25°C.

Uses of Calcipotriene: It is an antipsoriatic. A vitamin D3 analogue with low calcemic 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.

You can still convert the following datas into molecular structure:
(1)SMILES:O[C@@H]1CC(\C(=C)[C@@H](O)C1)=C\C=C2/CCC[C@]4([C@H]2CC[C@@H]4[C@@H](/C=C/[C@@H](O)C3CC3)C)C;
(2)Std. InChI:InChI=1S/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;
(3)Std. InChIKey:LWQQLNNNIPYSNX-UROSTWAQSA-N;

The toxicity data of Calcipotriene as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 skin > 1500ug/kg (1.5mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

MUSCULOSKELETAL: OTHER CHANGES

GASTROINTESTINAL: NAUSEA OR VOMITING		 Journal of Toxicological Sciences. Vol. 21(Suppl,
man TDLo skin 11gm/kg/11W-I (11000mg/kg)   British Medical Journal. Vol. 306, Pg. 896, 1993.
rat LD50 skin > 15mg/kg (15mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: ATAXIA		 Journal of Toxicological Sciences. Vol. 21(Suppl,
rat LD50 subcutaneous 2190ug/kg (2.19mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD		 Journal of Toxicological Sciences. Vol. 21(Suppl,
women TDLo skin 10gm/kg/6W-I (10000mg/kg)   British Medical Journal. Vol. 306, Pg. 896, 1993.

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