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Cas Database

115648-67-4

115648-67-4

Identification

  • Product Name:1(S),3(R)-bis<(tert-butyldimethylsilyl)oxy>-20(R)-formyl-9,10-secopregna-5(E),7(E),10(19)-triene

  • CAS Number: 115648-67-4

  • EINECS:

  • Molecular Weight:573.02

  • Molecular Formula: C34H60O3Si2

  • HS Code:

  • Mol File:115648-67-4.mol

Synonyms:1(S),3(R)-bis<(tert-butyldimethylsilyl)oxy>-20(R)-formyl-9,10-secopregna-5(E),7(E),10(19)-triene

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Relevant articles and documentsAll total 2 Articles be found

Synthesis of a Biologically Active Vitamine-D2 Metabolite

Choudhry, Satish C.,Belica, Peter S.,Coffen, David L.,Focella, Antonino,Maehr, Hubert,et al.

, p. 1496 - 1500 (2007/10/02)

The synthesis of 1α,25,28-trihydroxyvitamin-D2 (1) from vitamin-D2 is described.Approaches to the upper side-chain synthon via the chiral sulfone 15, prepared either through the enzymatic resolution of 10 or the opening of the optica

Synthesis of MC 903, a biologically active vitamin D metabolite analogue

Calverley

, p. 4609 - 4619,4609-4619 (2007/10/02)

-

Process route upstream and downstream products

Process route

(6S)- and (6R)-SO<sub>2</sub> adducts of 1(S),3(R)-bis(tert-butyldimethylsilyloxy)-20(S)-formyl-9,10-secopregna-5,7(E),10<sup>(19)</sup>-triene
266686-81-1

(6S)- and (6R)-SO2 adducts of 1(S),3(R)-bis(tert-butyldimethylsilyloxy)-20(S)-formyl-9,10-secopregna-5,7(E),10(19)-triene

(5E,7E)-(1S,3R,20S)-1,3-bis<<(1,1-dimethylethyl)dimethylsilyl>oxy>-20-methyl-9,10-secopregna-5,7,10(19)-trien-21-al
112828-13-4

(5E,7E)-(1S,3R,20S)-1,3-bis<<(1,1-dimethylethyl)dimethylsilyl>oxy>-20-methyl-9,10-secopregna-5,7,10(19)-trien-21-al

1(S),3(R)-bis<(tert-butyldimethylsilyl)oxy>-20(R)-formyl-9,10-secopregna-5(E),7(E),10(19)-triene
115648-67-4

1(S),3(R)-bis<(tert-butyldimethylsilyl)oxy>-20(R)-formyl-9,10-secopregna-5(E),7(E),10(19)-triene

Conditions
Conditions Yield
With sodium hydrogencarbonate; In ethanol; water; for 1.5h; Yields of byproduct given; Heating;
63%
tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

1(S),3(R)-bis<(tert-butyldimethylsilyl)oxy>-20(R)-formyl-9,10-secopregna-5(E),7(E),10(19)-triene
115648-67-4

1(S),3(R)-bis<(tert-butyldimethylsilyl)oxy>-20(R)-formyl-9,10-secopregna-5(E),7(E),10(19)-triene

Conditions
Conditions Yield
Multi-step reaction with 7 steps
1: 42 percent / imidazole / dimethylformamide / 1.5 h / 20 °C
2: sodium hydrogen carbonate / aq. ethanol / 1.5 h / Heating
3: N-methylmorpholine N-oxide monohydrate, selenium dioxide / CH2Cl2; methanol / 0.83 h / Heating
4: imidazole / dimethylformamide / 1.5 h / 20 °C
5: liq. SO2 / diethyl ether / 0.5 h / Heating
6: 1.) ozone 2.) PPh3 / 1.) CH2Cl2, MeOH, -60 deg C, 40 min. 2.) CH2Cl2, MeOH, -60 to 0 deg C
7: 5 percent / NaHCO3 / ethanol / 1.5 h / Heating
With 1H-imidazole; selenium(IV) oxide; sulfur dioxide; sodium hydrogencarbonate; ozone; 4-methylmorpholine N-oxide; triphenylphosphine; In methanol; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide;
Multi-step reaction with 7 steps
1: 42 percent / imidazole / dimethylformamide / 1.5 h / 20 °C
2: sodium hydrogen carbonate / aq. ethanol / 1.5 h / Heating
3: N-methylmorpholine N-oxide monohydrate, selenium dioxide / CH2Cl2; methanol / 0.83 h / Heating
4: imidazole / dimethylformamide / 1.5 h / 20 °C
5: liq. SO2 / diethyl ether / 0.5 h / Heating
6: 1.) ozone 2.) PPh3 / 1.) CH2Cl2, MeOH, -60 deg C, 40 min. 2.) CH2Cl2, MeOH, -60 to 0 deg C
7: 5 percent / NaHCO3 / ethanol / 1.5 h / Heating
With 1H-imidazole; selenium(IV) oxide; sulfur dioxide; sodium hydrogencarbonate; ozone; 4-methylmorpholine N-oxide; triphenylphosphine; In methanol; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide;
Multi-step reaction with 7 steps
1: 52 percent / imidazole / dimethylformamide / 1.5 h / 20 °C
2: sodium hydrogen carbonate / aq. ethanol / 1.5 h / Heating
3: N-methylmorpholine N-oxide monohydrate, selenium dioxide / CH2Cl2; methanol / 0.83 h / Heating
4: imidazole / dimethylformamide / 1.5 h / 20 °C
5: liq. SO2 / diethyl ether / 0.5 h / Heating
6: 1.) ozone 2.) PPh3 / 1.) CH2Cl2, MeOH, -60 deg C, 40 min. 2.) CH2Cl2, MeOH, -60 to 0 deg C
7: 5 percent / NaHCO3 / ethanol / 1.5 h / Heating
With 1H-imidazole; selenium(IV) oxide; sulfur dioxide; sodium hydrogencarbonate; ozone; 4-methylmorpholine N-oxide; triphenylphosphine; In methanol; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide;
Multi-step reaction with 7 steps
1: 52 percent / imidazole / dimethylformamide / 1.5 h / 20 °C
2: sodium hydrogen carbonate / aq. ethanol / 1.5 h / Heating
3: N-methylmorpholine N-oxide monohydrate, selenium dioxide / CH2Cl2; methanol / 0.83 h / Heating
4: imidazole / dimethylformamide / 1.5 h / 20 °C
5: liq. SO2 / diethyl ether / 0.5 h / Heating
6: 1.) ozone 2.) PPh3 / 1.) CH2Cl2, MeOH, -60 deg C, 40 min. 2.) CH2Cl2, MeOH, -60 to 0 deg C
7: 5 percent / NaHCO3 / ethanol / 1.5 h / Heating
With 1H-imidazole; selenium(IV) oxide; sulfur dioxide; sodium hydrogencarbonate; ozone; 4-methylmorpholine N-oxide; triphenylphosphine; In methanol; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide;
(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-2λ<sup>6</sup>-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

1(S),3(R)-bis<(tert-butyldimethylsilyl)oxy>-20(R)-formyl-9,10-secopregna-5(E),7(E),10(19)-triene
115648-67-4

1(S),3(R)-bis<(tert-butyldimethylsilyl)oxy>-20(R)-formyl-9,10-secopregna-5(E),7(E),10(19)-triene

Conditions
Conditions Yield
Multi-step reaction with 7 steps
1: 42 percent / imidazole / dimethylformamide / 1.5 h / 20 °C
2: sodium hydrogen carbonate / aq. ethanol / 1.5 h / Heating
3: N-methylmorpholine N-oxide monohydrate, selenium dioxide / CH2Cl2; methanol / 0.83 h / Heating
4: imidazole / dimethylformamide / 1.5 h / 20 °C
5: liq. SO2 / diethyl ether / 0.5 h / Heating
6: 1.) ozone 2.) PPh3 / 1.) CH2Cl2, MeOH, -60 deg C, 40 min. 2.) CH2Cl2, MeOH, -60 to 0 deg C
7: 5 percent / NaHCO3 / ethanol / 1.5 h / Heating
With 1H-imidazole; selenium(IV) oxide; sulfur dioxide; sodium hydrogencarbonate; ozone; 4-methylmorpholine N-oxide; triphenylphosphine; In methanol; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide;
Multi-step reaction with 7 steps
1: 42 percent / imidazole / dimethylformamide / 1.5 h / 20 °C
2: sodium hydrogen carbonate / aq. ethanol / 1.5 h / Heating
3: N-methylmorpholine N-oxide monohydrate, selenium dioxide / CH2Cl2; methanol / 0.83 h / Heating
4: imidazole / dimethylformamide / 1.5 h / 20 °C
5: liq. SO2 / diethyl ether / 0.5 h / Heating
6: 1.) ozone 2.) PPh3 / 1.) CH2Cl2, MeOH, -60 deg C, 40 min. 2.) CH2Cl2, MeOH, -60 to 0 deg C
7: 5 percent / NaHCO3 / ethanol / 1.5 h / Heating
With 1H-imidazole; selenium(IV) oxide; sulfur dioxide; sodium hydrogencarbonate; ozone; 4-methylmorpholine N-oxide; triphenylphosphine; In methanol; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide;
Multi-step reaction with 7 steps
1: 52 percent / imidazole / dimethylformamide / 1.5 h / 20 °C
2: sodium hydrogen carbonate / aq. ethanol / 1.5 h / Heating
3: N-methylmorpholine N-oxide monohydrate, selenium dioxide / CH2Cl2; methanol / 0.83 h / Heating
4: imidazole / dimethylformamide / 1.5 h / 20 °C
5: liq. SO2 / diethyl ether / 0.5 h / Heating
6: 1.) ozone 2.) PPh3 / 1.) CH2Cl2, MeOH, -60 deg C, 40 min. 2.) CH2Cl2, MeOH, -60 to 0 deg C
7: 5 percent / NaHCO3 / ethanol / 1.5 h / Heating
With 1H-imidazole; selenium(IV) oxide; sulfur dioxide; sodium hydrogencarbonate; ozone; 4-methylmorpholine N-oxide; triphenylphosphine; In methanol; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide;
Multi-step reaction with 7 steps
1: 52 percent / imidazole / dimethylformamide / 1.5 h / 20 °C
2: sodium hydrogen carbonate / aq. ethanol / 1.5 h / Heating
3: N-methylmorpholine N-oxide monohydrate, selenium dioxide / CH2Cl2; methanol / 0.83 h / Heating
4: imidazole / dimethylformamide / 1.5 h / 20 °C
5: liq. SO2 / diethyl ether / 0.5 h / Heating
6: 1.) ozone 2.) PPh3 / 1.) CH2Cl2, MeOH, -60 deg C, 40 min. 2.) CH2Cl2, MeOH, -60 to 0 deg C
7: 5 percent / NaHCO3 / ethanol / 1.5 h / Heating
With 1H-imidazole; selenium(IV) oxide; sulfur dioxide; sodium hydrogencarbonate; ozone; 4-methylmorpholine N-oxide; triphenylphosphine; In methanol; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide;
(7Z)-Vitamin D<sub>2</sub>
247900-07-8

(7Z)-Vitamin D2

1(S),3(R)-bis<(tert-butyldimethylsilyl)oxy>-20(R)-formyl-9,10-secopregna-5(E),7(E),10(19)-triene
115648-67-4

1(S),3(R)-bis<(tert-butyldimethylsilyl)oxy>-20(R)-formyl-9,10-secopregna-5(E),7(E),10(19)-triene

Conditions
Conditions Yield
Multi-step reaction with 8 steps
1: liq. SO2 / 0.5 h / Heating
2: 42 percent / imidazole / dimethylformamide / 1.5 h / 20 °C
3: sodium hydrogen carbonate / aq. ethanol / 1.5 h / Heating
4: N-methylmorpholine N-oxide monohydrate, selenium dioxide / CH2Cl2; methanol / 0.83 h / Heating
5: imidazole / dimethylformamide / 1.5 h / 20 °C
6: liq. SO2 / diethyl ether / 0.5 h / Heating
7: 1.) ozone 2.) PPh3 / 1.) CH2Cl2, MeOH, -60 deg C, 40 min. 2.) CH2Cl2, MeOH, -60 to 0 deg C
8: 5 percent / NaHCO3 / ethanol / 1.5 h / Heating
With 1H-imidazole; selenium(IV) oxide; sulfur dioxide; sodium hydrogencarbonate; ozone; 4-methylmorpholine N-oxide; triphenylphosphine; In methanol; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide;
Multi-step reaction with 8 steps
1: liq. SO2 / 0.5 h / Heating
2: 42 percent / imidazole / dimethylformamide / 1.5 h / 20 °C
3: sodium hydrogen carbonate / aq. ethanol / 1.5 h / Heating
4: N-methylmorpholine N-oxide monohydrate, selenium dioxide / CH2Cl2; methanol / 0.83 h / Heating
5: imidazole / dimethylformamide / 1.5 h / 20 °C
6: liq. SO2 / diethyl ether / 0.5 h / Heating
7: 1.) ozone 2.) PPh3 / 1.) CH2Cl2, MeOH, -60 deg C, 40 min. 2.) CH2Cl2, MeOH, -60 to 0 deg C
8: 5 percent / NaHCO3 / ethanol / 1.5 h / Heating
With 1H-imidazole; selenium(IV) oxide; sulfur dioxide; sodium hydrogencarbonate; ozone; 4-methylmorpholine N-oxide; triphenylphosphine; In methanol; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide;
Multi-step reaction with 8 steps
1: liq. SO2 / 0.5 h / Heating
2: 52 percent / imidazole / dimethylformamide / 1.5 h / 20 °C
3: sodium hydrogen carbonate / aq. ethanol / 1.5 h / Heating
4: N-methylmorpholine N-oxide monohydrate, selenium dioxide / CH2Cl2; methanol / 0.83 h / Heating
5: imidazole / dimethylformamide / 1.5 h / 20 °C
6: liq. SO2 / diethyl ether / 0.5 h / Heating
7: 1.) ozone 2.) PPh3 / 1.) CH2Cl2, MeOH, -60 deg C, 40 min. 2.) CH2Cl2, MeOH, -60 to 0 deg C
8: 5 percent / NaHCO3 / ethanol / 1.5 h / Heating
With 1H-imidazole; selenium(IV) oxide; sulfur dioxide; sodium hydrogencarbonate; ozone; 4-methylmorpholine N-oxide; triphenylphosphine; In methanol; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide;
Multi-step reaction with 8 steps
1: liq. SO2 / 0.5 h / Heating
2: 52 percent / imidazole / dimethylformamide / 1.5 h / 20 °C
3: sodium hydrogen carbonate / aq. ethanol / 1.5 h / Heating
4: N-methylmorpholine N-oxide monohydrate, selenium dioxide / CH2Cl2; methanol / 0.83 h / Heating
5: imidazole / dimethylformamide / 1.5 h / 20 °C
6: liq. SO2 / diethyl ether / 0.5 h / Heating
7: 1.) ozone 2.) PPh3 / 1.) CH2Cl2, MeOH, -60 deg C, 40 min. 2.) CH2Cl2, MeOH, -60 to 0 deg C
8: 5 percent / NaHCO3 / ethanol / 1.5 h / Heating
With 1H-imidazole; selenium(IV) oxide; sulfur dioxide; sodium hydrogencarbonate; ozone; 4-methylmorpholine N-oxide; triphenylphosphine; In methanol; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide;
(6R)-SO<sub>2</sub> adduct of 1(S),3(R)-bis(tert-butyldimethylsilyloxy)-20(S)-formyl-9,10-secopregna-5,7(E),10<sup>(19)</sup>-triene
112790-51-9,266686-81-1

(6R)-SO2 adduct of 1(S),3(R)-bis(tert-butyldimethylsilyloxy)-20(S)-formyl-9,10-secopregna-5,7(E),10(19)-triene

(5E,7E)-(1S,3R,20S)-1,3-bis<<(1,1-dimethylethyl)dimethylsilyl>oxy>-20-methyl-9,10-secopregna-5,7,10(19)-trien-21-al
112828-13-4

(5E,7E)-(1S,3R,20S)-1,3-bis<<(1,1-dimethylethyl)dimethylsilyl>oxy>-20-methyl-9,10-secopregna-5,7,10(19)-trien-21-al

1(S),3(R)-bis<(tert-butyldimethylsilyl)oxy>-20(R)-formyl-9,10-secopregna-5(E),7(E),10(19)-triene
115648-67-4

1(S),3(R)-bis<(tert-butyldimethylsilyl)oxy>-20(R)-formyl-9,10-secopregna-5(E),7(E),10(19)-triene

Conditions
Conditions Yield
With sodium hydrogencarbonate; In ethanol; for 1.5h; Heating;
5%
90%
(6S)-SO<sub>2</sub> adduct of 1(S),3(R)-bis(tert-butyldimethylsilyloxy)-20(S)-formyl-9,10-secopregna-5,7(E),10<sup>(19)</sup>-triene
112670-80-1,266686-81-1

(6S)-SO2 adduct of 1(S),3(R)-bis(tert-butyldimethylsilyloxy)-20(S)-formyl-9,10-secopregna-5,7(E),10(19)-triene

(5E,7E)-(1S,3R,20S)-1,3-bis<<(1,1-dimethylethyl)dimethylsilyl>oxy>-20-methyl-9,10-secopregna-5,7,10(19)-trien-21-al
112828-13-4

(5E,7E)-(1S,3R,20S)-1,3-bis<<(1,1-dimethylethyl)dimethylsilyl>oxy>-20-methyl-9,10-secopregna-5,7,10(19)-trien-21-al

1(S),3(R)-bis<(tert-butyldimethylsilyl)oxy>-20(R)-formyl-9,10-secopregna-5(E),7(E),10(19)-triene
115648-67-4

1(S),3(R)-bis<(tert-butyldimethylsilyl)oxy>-20(R)-formyl-9,10-secopregna-5(E),7(E),10(19)-triene

Conditions
Conditions Yield
With sodium hydrogencarbonate; In ethanol; for 1.5h; Heating;
5%
90%
1(S),3(R)-bis(tert-butyldimethylsilyloxy)-9,10-secoergosta-5(E),7(E),10<sup>(19)</sup>,22(E)-tetraene
115540-28-8,125136-23-4,111594-58-2,184851-16-9

1(S),3(R)-bis(tert-butyldimethylsilyloxy)-9,10-secoergosta-5(E),7(E),10(19),22(E)-tetraene

1(S),3(R)-bis<(tert-butyldimethylsilyl)oxy>-20(R)-formyl-9,10-secopregna-5(E),7(E),10(19)-triene
115648-67-4

1(S),3(R)-bis<(tert-butyldimethylsilyl)oxy>-20(R)-formyl-9,10-secopregna-5(E),7(E),10(19)-triene

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1: liq. SO2 / diethyl ether / 0.5 h / Heating
2: 1.) ozone 2.) PPh3 / 1.) CH2Cl2, MeOH, -60 deg C, 40 min. 2.) CH2Cl2, MeOH, -60 to 0 deg C
3: 5 percent / NaHCO3 / ethanol / 1.5 h / Heating
With sulfur dioxide; sodium hydrogencarbonate; ozone; triphenylphosphine; In diethyl ether; ethanol;
Multi-step reaction with 3 steps
1: liq. SO2 / diethyl ether / 0.5 h / Heating
2: 1.) ozone 2.) PPh3 / 1.) CH2Cl2, MeOH, -60 deg C, 40 min. 2.) CH2Cl2, MeOH, -60 to 0 deg C
3: 5 percent / NaHCO3 / ethanol / 1.5 h / Heating
With sulfur dioxide; sodium hydrogencarbonate; ozone; triphenylphosphine; In diethyl ether; ethanol;
(5E)-vitamin D<sub>2</sub> tert-butyldimethylsilyl ether
104846-62-0,104846-63-1

(5E)-vitamin D2 tert-butyldimethylsilyl ether

1(S),3(R)-bis<(tert-butyldimethylsilyl)oxy>-20(R)-formyl-9,10-secopregna-5(E),7(E),10(19)-triene
115648-67-4

1(S),3(R)-bis<(tert-butyldimethylsilyl)oxy>-20(R)-formyl-9,10-secopregna-5(E),7(E),10(19)-triene

Conditions
Conditions Yield
Multi-step reaction with 5 steps
1: N-methylmorpholine N-oxide monohydrate, selenium dioxide / CH2Cl2; methanol / 0.83 h / Heating
2: imidazole / dimethylformamide / 1.5 h / 20 °C
3: liq. SO2 / diethyl ether / 0.5 h / Heating
4: 1.) ozone 2.) PPh3 / 1.) CH2Cl2, MeOH, -60 deg C, 40 min. 2.) CH2Cl2, MeOH, -60 to 0 deg C
5: 5 percent / NaHCO3 / ethanol / 1.5 h / Heating
With 1H-imidazole; selenium(IV) oxide; sulfur dioxide; sodium hydrogencarbonate; ozone; 4-methylmorpholine N-oxide; triphenylphosphine; In methanol; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide;
Multi-step reaction with 5 steps
1: N-methylmorpholine N-oxide monohydrate, selenium dioxide / CH2Cl2; methanol / 0.83 h / Heating
2: imidazole / dimethylformamide / 1.5 h / 20 °C
3: liq. SO2 / diethyl ether / 0.5 h / Heating
4: 1.) ozone 2.) PPh3 / 1.) CH2Cl2, MeOH, -60 deg C, 40 min. 2.) CH2Cl2, MeOH, -60 to 0 deg C
5: 5 percent / NaHCO3 / ethanol / 1.5 h / Heating
With 1H-imidazole; selenium(IV) oxide; sulfur dioxide; sodium hydrogencarbonate; ozone; 4-methylmorpholine N-oxide; triphenylphosphine; In methanol; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide;
(3S,6R)-(tert-butyldimethylsilyloxy)-9,10-seco-ergosta-5,7(E),10<sup>(19)</sup>,22(E)-tetraene SO<sub>2</sub> adduct
87417-26-3,251445-16-6

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

1(S),3(R)-bis<(tert-butyldimethylsilyl)oxy>-20(R)-formyl-9,10-secopregna-5(E),7(E),10(19)-triene
115648-67-4

1(S),3(R)-bis<(tert-butyldimethylsilyl)oxy>-20(R)-formyl-9,10-secopregna-5(E),7(E),10(19)-triene

Conditions
Conditions Yield
Multi-step reaction with 6 steps
1: sodium hydrogen carbonate / aq. ethanol / 1.5 h / Heating
2: N-methylmorpholine N-oxide monohydrate, selenium dioxide / CH2Cl2; methanol / 0.83 h / Heating
3: imidazole / dimethylformamide / 1.5 h / 20 °C
4: liq. SO2 / diethyl ether / 0.5 h / Heating
5: 1.) ozone 2.) PPh3 / 1.) CH2Cl2, MeOH, -60 deg C, 40 min. 2.) CH2Cl2, MeOH, -60 to 0 deg C
6: 5 percent / NaHCO3 / ethanol / 1.5 h / Heating
With 1H-imidazole; selenium(IV) oxide; sulfur dioxide; sodium hydrogencarbonate; ozone; 4-methylmorpholine N-oxide; triphenylphosphine; In methanol; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide;
Multi-step reaction with 6 steps
1: sodium hydrogen carbonate / aq. ethanol / 1.5 h / Heating
2: N-methylmorpholine N-oxide monohydrate, selenium dioxide / CH2Cl2; methanol / 0.83 h / Heating
3: imidazole / dimethylformamide / 1.5 h / 20 °C
4: liq. SO2 / diethyl ether / 0.5 h / Heating
5: 1.) ozone 2.) PPh3 / 1.) CH2Cl2, MeOH, -60 deg C, 40 min. 2.) CH2Cl2, MeOH, -60 to 0 deg C
6: 5 percent / NaHCO3 / ethanol / 1.5 h / Heating
With 1H-imidazole; selenium(IV) oxide; sulfur dioxide; sodium hydrogencarbonate; ozone; 4-methylmorpholine N-oxide; triphenylphosphine; In methanol; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide;
(3S,6S)-(tert-butyldimethylsilyloxy)-9,10-seco-ergosta-5,7(E),10<sup>(19)</sup>,22(E)-tetraene SO<sub>2</sub>-adduct
87417-26-3,87417-27-4,251445-16-6

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

1(S),3(R)-bis<(tert-butyldimethylsilyl)oxy>-20(R)-formyl-9,10-secopregna-5(E),7(E),10(19)-triene
115648-67-4

1(S),3(R)-bis<(tert-butyldimethylsilyl)oxy>-20(R)-formyl-9,10-secopregna-5(E),7(E),10(19)-triene

Conditions
Conditions Yield
Multi-step reaction with 6 steps
1: sodium hydrogen carbonate / aq. ethanol / 1.5 h / Heating
2: N-methylmorpholine N-oxide monohydrate, selenium dioxide / CH2Cl2; methanol / 0.83 h / Heating
3: imidazole / dimethylformamide / 1.5 h / 20 °C
4: liq. SO2 / diethyl ether / 0.5 h / Heating
5: 1.) ozone 2.) PPh3 / 1.) CH2Cl2, MeOH, -60 deg C, 40 min. 2.) CH2Cl2, MeOH, -60 to 0 deg C
6: 5 percent / NaHCO3 / ethanol / 1.5 h / Heating
With 1H-imidazole; selenium(IV) oxide; sulfur dioxide; sodium hydrogencarbonate; ozone; 4-methylmorpholine N-oxide; triphenylphosphine; In methanol; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide;
Multi-step reaction with 6 steps
1: sodium hydrogen carbonate / aq. ethanol / 1.5 h / Heating
2: N-methylmorpholine N-oxide monohydrate, selenium dioxide / CH2Cl2; methanol / 0.83 h / Heating
3: imidazole / dimethylformamide / 1.5 h / 20 °C
4: liq. SO2 / diethyl ether / 0.5 h / Heating
5: 1.) ozone 2.) PPh3 / 1.) CH2Cl2, MeOH, -60 deg C, 40 min. 2.) CH2Cl2, MeOH, -60 to 0 deg C
6: 5 percent / NaHCO3 / ethanol / 1.5 h / Heating
With 1H-imidazole; selenium(IV) oxide; sulfur dioxide; sodium hydrogencarbonate; ozone; 4-methylmorpholine N-oxide; triphenylphosphine; In methanol; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide;

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