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112849-27-1

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Bis-TBDMS-trans-calcipotriol
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1,3-bi-TBS-trans-Calcipotriol
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Manufacture Calcipotriol Intermediate Bis-TBDMS-trans-calcipotriol
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24-Cyclopropyl-1,3-bis-[[(1,1-dimethylethyl)-dimethylsilyl]-oxy]-9,10-secochola-5,7,10(19),22-tetraen-24-ol
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112849-27-1 Usage

Chemical Properties

Clear Oil

Uses

Protected trans-Calcipotriol, a vitamin D analog.
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)17-20-31-25-32(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,2,14-15,18-19,21-22,24-26H2,1,3-13H3/b23-16+,29-17+,31-20+/t27-,32-,33-,34+,35-,36?,39?/m1/s1

112849-27-1SDS

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 Bis-TBDMS-trans-calcipotriol

1.2 Other means of identification

Product number -
Other names Trans-Calcipotriol-bis-TBDMS-ether

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:112849-27-1 SDS

112849-27-1Synthetic 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;
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;
(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
(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;

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