Product Name

  • Name

    Bis-TBDMS-trans-calcipotriol

  • EINECS 1312995-182-4
  • CAS No. 112849-27-1
  • Article Data5
  • CAS DataBase
  • Density 0.988 g/cm3
  • Solubility
  • Melting Point
  • Formula C39H68O3Si2
  • Boiling Point 628.182 °C at 760 mmHg
  • Molecular Weight 641.138
  • Flash Point 333.713 °C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 112849-27-1 (Bis-TBDMS-trans-calcipotriol)
  • Hazard Symbols
  • Synonyms 9,10-Secochola-5,7,10(19),22-tetraen-24-ol,24-cyclopropyl-1,3-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-, (1a,3b,5E,7E,22E,24S)- (9CI);
  • PSA 38.69000
  • LogP 11.14960

Synthetic route

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

A

(1S,3R,3'R)-bis(tert-butyldimethylsilyloxy)-20(R)-(3'-cyclopropyl-3'-hydroxyprop-1'(E)-enyl)-9,10-secopregna-5(E),7(E),10(19)-triene
112849-26-0

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

B

(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

Conditions
ConditionsYield
With sodium tetrahydroborate; cerium(III) chloride In methanol further reag.: (S)-BINAL-H;A 55%
B 33%
Stage #1: 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 With borane N,N-diethylaniline complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole In tetrahydrofuran; toluene at 0 - 5℃; for 2.66667 - 3.58333h;
Stage #2: With water; sodium hydrogencarbonate In tetrahydrofuran; toluene at 0 - 5℃;
(1S,3R,3'R)-bis(tert-butyldimethylsilyloxy)-20(R)-(3'-cyclopropyl-3'-hydroxyprop-1'(E)-enyl)-9,10-secopregna-5(E),7(E),10(19)-triene
112849-26-0

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

(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

Conditions
ConditionsYield
With sulfuric acid In tetrahydrofuran; water at 20℃; pH=1.7;45%
With sodium hydrogen sulfate In tetrahydrofuran; water; acetone at 20 - 25℃; for 3.66667h; pH=1.58;
With sulfuric acid In water; ethyl acetate; acetone at 27℃; for 0.583333h; pH=1.25;
With phosphoric acid In tetrahydrofuran; water; acetone at 20℃; for 19h; pH=1.48;
With phosphoric acid In tetrahydrofuran; water; acetone at 30℃; for 6h; pH=1.01;
Cyclopropyl methyl ketone
765-43-5

Cyclopropyl methyl ketone

(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

Conditions
ConditionsYield
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
5: N-methylmorpholine N-oxide, selenium dioxide
6: imidazole / dimethylformamide
7: 33 percent / NaBH4, CeCl3*6H2O / methanol / further reag.: (S)-BINAL-H
View Scheme
Multi-step reaction with 5 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
View Scheme
2-bromo-1-cyclopropylethan-1-one
69267-75-0

2-bromo-1-cyclopropylethan-1-one

(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

Conditions
ConditionsYield
Multi-step reaction with 6 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
View Scheme
Multi-step reaction with 4 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
View Scheme
1-cyclopropyl-2-(triphenyl-λ5-phosphanylidene)ethan-1-one
7691-76-1

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

(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

Conditions
ConditionsYield
Multi-step reaction with 4 steps
2: N-methylmorpholine N-oxide, selenium dioxide
3: imidazole / dimethylformamide
4: 33 percent / NaBH4, CeCl3*6H2O / methanol / further reag.: (S)-BINAL-H
View Scheme
Multi-step reaction with 2 steps
1: dimethylsulfoxide / 4 h / 105 °C
2: 33 percent / NaBH4, CeCl3*6H2O / methanol / further reag.: (S)-BINAL-H
View Scheme
tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

(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

Conditions
ConditionsYield
Multi-step reaction with 7 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
View Scheme
Multi-step reaction with 7 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
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

(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

Conditions
ConditionsYield
Multi-step reaction with 4 steps
2: N-methylmorpholine N-oxide, selenium dioxide
3: imidazole / dimethylformamide
4: 33 percent / NaBH4, CeCl3*6H2O / methanol / further reag.: (S)-BINAL-H
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

(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

Conditions
ConditionsYield
Multi-step reaction with 7 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
View Scheme
Multi-step reaction with 7 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
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

(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

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: N-methylmorpholine N-oxide, selenium dioxide
2: imidazole / dimethylformamide
3: 33 percent / NaBH4, CeCl3*6H2O / methanol / further reag.: (S)-BINAL-H
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

(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

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: imidazole / dimethylformamide
2: 33 percent / NaBH4, CeCl3*6H2O / methanol / further reag.: (S)-BINAL-H
View Scheme
(2-cyclopropyl-2-oxoethyl) (triphenyl)phosphonium bromide
112849-15-7

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

(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

Conditions
ConditionsYield
Multi-step reaction with 5 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
View Scheme
Multi-step reaction with 3 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
View Scheme
(7Z)-Vitamin D2
247900-07-8

(7Z)-Vitamin D2

(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

Conditions
ConditionsYield
Multi-step reaction with 8 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
View Scheme
Multi-step reaction with 8 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
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

(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

Conditions
ConditionsYield
Multi-step reaction with 5 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
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

(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

Conditions
ConditionsYield
Multi-step reaction with 5 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
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

(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

Conditions
ConditionsYield
Multi-step reaction with 6 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
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

(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

Conditions
ConditionsYield
Multi-step reaction with 6 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
View Scheme
C42H72O4Si2

C42H72O4Si2

A

(1S,3R,3'R)-bis(tert-butyldimethylsilyloxy)-20(R)-(3'-cyclopropyl-3'-hydroxyprop-1'(E)-enyl)-9,10-secopregna-5(E),7(E),10(19)-triene
112849-26-0

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

B

(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

Conditions
ConditionsYield
Stage #1: C42H72O4Si2 With silica gel In hexane; ethyl acetate at 20℃; Reaction on a column;
Stage #2: With potassium carbonate In tetrahydrofuran; methanol Product distribution / selectivity;		A n/a
B n/a
C46H71NO6Si2

C46H71NO6Si2

A

(1S,3R,3'R)-bis(tert-butyldimethylsilyloxy)-20(R)-(3'-cyclopropyl-3'-hydroxyprop-1'(E)-enyl)-9,10-secopregna-5(E),7(E),10(19)-triene
112849-26-0

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

B

(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

Conditions
ConditionsYield
With silica gel In hexane; ethyl acetate Product distribution / selectivity; Mitsunobu reaction;
C41H70O4Si2

C41H70O4Si2

A

(1S,3R,3'R)-bis(tert-butyldimethylsilyloxy)-20(R)-(3'-cyclopropyl-3'-hydroxyprop-1'(E)-enyl)-9,10-secopregna-5(E),7(E),10(19)-triene
112849-26-0

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

B

(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

Conditions
ConditionsYield
With silica gel In hexane at 0 - 40℃; for 2.5 - 26h; Product distribution / selectivity;A n/a
B n/a
With silica gel; potassium carbonate In hexane for 48h; Product distribution / selectivity;
With silica gel; triethylamine In hexane for 7h; Product distribution / selectivity;
1(S),3(R)-bis(tert-butyldimethylsilyloxy)-20(R)-(3'-cyclopropyl-3'-oxoprop-1'(E)-enyl)-9,10-secopregna-5(E),7(E),10(19)-triene SO2-adducts

1(S),3(R)-bis(tert-butyldimethylsilyloxy)-20(R)-(3'-cyclopropyl-3'-oxoprop-1'(E)-enyl)-9,10-secopregna-5(E),7(E),10(19)-triene SO2-adducts

A

(1S,3R,3'R)-bis(tert-butyldimethylsilyloxy)-20(R)-(3'-cyclopropyl-3'-hydroxyprop-1'(E)-enyl)-9,10-secopregna-5(E),7(E),10(19)-triene
112849-26-0

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

B

(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

Conditions
ConditionsYield
Stage #1: 1(S),3(R)-bis(tert-butyldimethylsilyloxy)-20(R)-(3'-cyclopropyl-3'-oxoprop-1'(E)-enyl)-9,10-secopregna-5(E),7(E),10(19)-triene SO2-adducts With borane Ν,Ν-diethylaniline complex; (1S,2R)-1-amino-2-indanol In tert-butyl methyl ether; toluene at 10 - 25℃; for 0.5 - 1h;
Stage #2: With hydrogenchloride In tert-butyl methyl ether; water; toluene at 10 - 15℃;
Stage #3: With sodium hydrogencarbonate In water at 90℃; for 2 - 2.5h; Product distribution / selectivity;
Stage #1: 1(S),3(R)-bis(tert-butyldimethylsilyloxy)-20(R)-(3'-cyclopropyl-3'-oxoprop-1'(E)-enyl)-9,10-secopregna-5(E),7(E),10(19)-triene SO2-adducts With dimethylsulfide borane complex; (1S,2R)-1-amino-2-indanol In tert-butyl methyl ether; toluene at 15 - 20℃; for 0.5 - 1h;
Stage #2: With hydrogenchloride In tert-butyl methyl ether; water; toluene at 10 - 15℃;
Stage #3: With sodium hydrogencarbonate In water at 90℃; for 2 - 2.5h; Product distribution / selectivity;
Stage #1: 1(S),3(R)-bis(tert-butyldimethylsilyloxy)-20(R)-(3'-cyclopropyl-3'-oxoprop-1'(E)-enyl)-9,10-secopregna-5(E),7(E),10(19)-triene SO2-adducts With borane Ν,Ν-diethylaniline complex; (R)-α,α-diphenylprolinol In tert-butyl methyl ether; toluene at 15 - 20℃; for 0.5 - 1h;
Stage #2: With hydrogenchloride In tert-butyl methyl ether; water; toluene at 10 - 15℃;
Stage #3: With sodium hydrogencarbonate In water at 90℃; for 2 - 2.5h; Product distribution / selectivity;
SO2-adduct of 1(S),3(R)-bis(tert-butyl-dimethylsilyloxy)-20(R)-(3'-cyclopropyl-3'(S)-hydroxyprop-1'(E)-enyl)-9,10-secopregna-5(E),7(E),10(19)-triene

SO2-adduct of 1(S),3(R)-bis(tert-butyl-dimethylsilyloxy)-20(R)-(3'-cyclopropyl-3'(S)-hydroxyprop-1'(E)-enyl)-9,10-secopregna-5(E),7(E),10(19)-triene

SO2-adduct of 1(S),3(R)-bis(tert-butyl-dimethylsilyloxy)-20(R)-(3'-cyclopropyl-3'(R)-hydroxyprop-1'(E)-enyl)-9,10-secopregna-5(E),7(E),10(19)-triene
878285-87-1

SO2-adduct of 1(S),3(R)-bis(tert-butyl-dimethylsilyloxy)-20(R)-(3'-cyclopropyl-3'(R)-hydroxyprop-1'(E)-enyl)-9,10-secopregna-5(E),7(E),10(19)-triene

A

(1S,3R,3'R)-bis(tert-butyldimethylsilyloxy)-20(R)-(3'-cyclopropyl-3'-hydroxyprop-1'(E)-enyl)-9,10-secopregna-5(E),7(E),10(19)-triene
112849-26-0

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

B

(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

Conditions
ConditionsYield
With sodium hydrogencarbonate In water at 90℃; for 2 - 2.5h; Retro Diels-Alder Reaction;
...Expand
C39H70O5SSi2

C39H70O5SSi2

C39H70O5SSi2

C39H70O5SSi2

C39H70O5SSi2

C39H70O5SSi2

C39H70O5SSi2

C39H70O5SSi2

A

(1S,3R,3'R)-bis(tert-butyldimethylsilyloxy)-20(R)-(3'-cyclopropyl-3'-hydroxyprop-1'(E)-enyl)-9,10-secopregna-5(E),7(E),10(19)-triene
112849-26-0

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

B

(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

Conditions
ConditionsYield
With sodium hydrogencarbonate In tert-butyl methyl ether; water; toluene at 90℃; for 2 - 2.5h; retro Diels-Alder Reaction;
...Expand
(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

(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

Conditions
ConditionsYield
With anthracene; triethylamine In toluene at 20℃; for 1h; Irradiation;
With 9-acetylanthracene; triethylamine In toluene at 5 - 8℃; for 0.75h; UV-irradiation;
With 9-acetylanthracene In toluene at 20℃; UV-irradiation;
9-acetylanthracene In tert-butyl methyl ether at 10℃; Industry scale; Irradiation;
With anthracene; triethylamine In toluene at 20 - 25℃; UV-irradiation;
(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

(1S,3R,1'S,2'S,3'S)-(3'-cyclopropyl-1',2'-epoxy-3'-hydroxypropyl)-9,10-secopregna-5(E),7(E),10(19)-triene
115540-29-9, 115540-30-2, 115540-31-3, 115598-01-1

(1S,3R,1'S,2'S,3'S)-(3'-cyclopropyl-1',2'-epoxy-3'-hydroxypropyl)-9,10-secopregna-5(E),7(E),10(19)-triene

Conditions
ConditionsYield
With titanium(IV) isopropylate; tert.-butylhydroperoxide; (+)-Weinsaeure-diethylester In dichloromethane at -20℃; further reag.: (-)-diethyl tartrate; Yield given;
(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

A

(1S,3R,1'S,2'S,3'S)-(3'-cyclopropyl-1',2'-epoxy-3'-hydroxypropyl)-9,10-secopregna-5(E),7(E),10(19)-triene
115540-29-9, 115540-30-2, 115540-31-3, 115598-01-1

(1S,3R,1'S,2'S,3'S)-(3'-cyclopropyl-1',2'-epoxy-3'-hydroxypropyl)-9,10-secopregna-5(E),7(E),10(19)-triene

B

(1S,3R,1'R,2'R,3'S)-(3'-cyclopropyl-1',2'-epoxy-3'-hydroxypropyl)-9,10-secopregna-5(E),7(E),10(19)-triene
115540-29-9, 115540-30-2, 115540-31-3, 115598-01-1

(1S,3R,1'R,2'R,3'S)-(3'-cyclopropyl-1',2'-epoxy-3'-hydroxypropyl)-9,10-secopregna-5(E),7(E),10(19)-triene

Conditions
ConditionsYield
With titanium(IV) isopropylate; tert.-butylhydroperoxide; (-)-diethyl tartrate In dichloromethane at -20℃; further reag.: (+)-diethyl tartrate; Yield given. Yields of byproduct given;
(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
vinyl acetate
108-05-4

vinyl acetate

(1S,3R,3'R)-bis(tert-butyldimethylsilyloxy)-20(R)-(3'-cyclopropyl-3'-hydroxyprop-1'(E)-enyl)-9,10-secopregna-5(E),7(E),10(19)-triene
112849-26-0

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

(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

C41H70O4Si2

C41H70O4Si2

Conditions
ConditionsYield
Alcaligenes sp. lipase In hexane at 22 - 28℃; for 3h; Enzymatic reaction;n/a
Alcaligenes sp. lipase In di-isopropyl ether at 20℃; for 2h; Enzymatic reaction;n/a
...Expand
(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

4-nitro-benzoic acid
62-23-7

4-nitro-benzoic acid

C46H71NO6Si2

C46H71NO6Si2

Conditions
ConditionsYield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 60℃; for 4.5h; Mitsunobu reaction;n/a
C41H70O4Si2
565429-98-3

C41H70O4Si2

(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

(1S,3R,3'R)-bis(tert-butyldimethylsilyloxy)-20(R)-(3'-cyclopropyl-3'-hydroxyprop-1'(E)-enyl)-9,10-secopregna-5(E),7(E),10(19)-triene
112849-26-0

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

Conditions
ConditionsYield
With silica gel In hexane for 1.5h; Product distribution / selectivity;
(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

A

C39H68O3Si2

C39H68O3Si2

B

(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

Conditions
ConditionsYield
9-acetylanthracene In tert-butyl methyl ether at 10℃; Product distribution / selectivity; UV-irradiation;
9-acetylanthracene In tert-butyl methyl ether at 10℃; Product distribution / selectivity; UV-irradiation;

Bis-TBDMS-trans-calcipotriol Chemical Properties

Molecule structure of Bis-TBDMS-trans-calcipotriol (CAS NO.112849-27-1):

Molecular Weight: 641.1264 g/mol
Molecular Formula: C39H68O3Si2
Density: 0.988 g/cm3 
Boiling Point: 628.182 °C at 760 mmHg 
Flash Point: 333.713 °C
Index of Refraction: 1.515
Molar Refractivity: 195.675 cm3
Molar Volume: 649.028 cm3
Polarizability: 77.571×10-24 cm3
Surface Tension: 34.044 dyne/cm 
Enthalpy of Vaporization: 106.539 kJ/mol 
InChI: InChI=1/C39H68O3Si2/c1-27(16-23-35(40)30-18-19-30)33-21-22-34-29(15-14-24-39(33,34)9)17-20-31-25-2(41-43(10,11)37(3,4)5)26-36(28(31)2)42-44(12,13)38(6,7)8/h16-17,20,23,27,30,32-36,40H,2,14-15,18-19,21-22,24-6H2,1,3-13H3/b23-16+,29-17+,31-20+/t27-,32-,33-,34+,35-,36,39/m1/s1
InChIKey of Bis-TBDMS-trans-calcipotriol (CAS NO.112849-27-1): DIMYHZDULFSWLS-HIKIKIINBJ

Bis-TBDMS-trans-calcipotriol Specification

 Bis-TBDMS-trans-calcipotriol (CAS NO.112849-27-1) is also named as 24-Cycloproyply-1,3-bis[[(1,1-dimethylethyl)dimethylsily]oxy]-9,10-secochola-5,7,10(19),22-tetraen-24-ol ; Cyclopropanemethanol, a-[(1E,3R)-3-[(1R,3aS,4E,7aR)-4-[(2E)-2-[(3S,5R)-3,5-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-methylenecyclohexylidene]ethylidene]octahydro-7a-methyl-1H-inden-1-yl]-1-buten-1-yl]-, (aS)- .

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