(1S,3R,5E,7E)-1,3-Bis-[(tert-butyldimethylsilyl)oxy]-9,10-secopregna-5,7,10-triene-20-carboxaldehyde

Base Information

• Chemical Name: (1S,3R,5E,7E)-1,3-Bis-[(tert-butyldimethylsilyl)oxy]-9,10-secopregna-5,7,10-triene-20-carboxaldehyde
• CAS No.: 112828-13-4
• Molecular Formula: C34H60O3Si2
• Molecular Weight: 573.02
• DSSTox Substance ID: DTXSID80448648
• Nikkaji Number: J2.738.478A
• Mol file: 112828-13-4.mol

Synonyms:112828-13-4;(1S,3R,5E,7E)-1,3-Bis-[(tert-butyldimethylsilyl)oxy]-9,10-secopregna-5,7,10-triene-20-carboxaldehyde;(2S)-2-[(1R,3aS,4E,7aR)-4-[(2E)-2-[(3S,5R)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-2-methylidenecyclohexylidene]ethylidene]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-1-yl]propanal;(S)-2-((1R,3aS,7aR,E)-4-((E)-2-((3S,5R)-3,5-bis(tert-butyldimethylsilyloxy)-2-methylenecyclohexylidene)ethylidene)-7a-methyloctahydro-1H-inden-1-yl)propanal;SCHEMBL8773164;DTXSID80448648;CS-M0454;AKOS037650110;CS-14290;2-[(1R,3aS,4E,7aR)-4-{(2E)-2-[(3S,5R)-3,5-Bis{[tert-butyl(dimethyl)silyl]oxy}-2-methylidenecyclohexylidene]ethylidene}-7a-methyloctahydro-1H-inden-1-yl]propanal (non-preferred name)

Chemical Property of (1S,3R,5E,7E)-1,3-Bis-[(tert-butyldimethylsilyl)oxy]-9,10-secopregna-5,7,10-triene-20-carboxaldehyde

Chemical Property:

• Boiling Point: 568.6±50.0 °C(Predicted)
• PSA: 35.53000
• Density: 0.96±0.1 g/cm3(Predicted)
• LogP: 10.02140
• Solubility.: Chloroform, Dichloromethane
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 9
• Exact Mass: 572.40809884
• Heavy Atom Count: 39
• Complexity: 977

Purity/Quality:

99%+ ^*data from raw suppliers

(1S,3R,5E,7E)-1,3-Bis-[(tert-butyldimethylsilyl)oxy]-9,10-secopregna-5,7,10-triene-20-carboxaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C=O)C1CCC2C1(CCCC2=CC=C3CC(CC(C3=C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C
• Isomeric SMILES: C[C@H](C=O)[C@H]1CC[C@@H]\2[C@@]1(CCC/C2=C\C=C\3/C[C@H](C[C@@H](C3=C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C
• Uses: Intermediate in the preparation of Vitamin D analogs.

Technology Process of (1S,3R,5E,7E)-1,3-Bis-[(tert-butyldimethylsilyl)oxy]-9,10-secopregna-5,7,10-triene-20-carboxaldehyde

There total 18 articles about (1S,3R,5E,7E)-1,3-Bis-[(tert-butyldimethylsilyl)oxy]-9,10-secopregna-5,7,10-triene-20-carboxaldehyde which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

(1S),3(R)-bis<(tert-butyldimethylsilyl)oxy>-20(S)-(hydroxymethyl)-9,10-secopregna-5(E),7(E),10(19)-triene (128387-35-9) → (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)

Guidance literature:

With tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide; In dichloromethane; Molecular sieve;

DOI:10.1016/j.tetlet.2009.06.049

Reference yield: 63.0%

(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 (266686-81-1) → (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) + 1(S),3(R)-bis<(tert-butyldimethylsilyl)oxy>-20(R)-formyl-9,10-secopregna-5(E),7(E),10(19)-triene (115648-67-4)

Guidance literature:

With sodium hydrogencarbonate; In ethanol; water; for 1.5h; Yields of byproduct given; Heating;

DOI:10.1021/jo00058a034

Reference yield: 5.0%

(6R)-SO2 adduct of 1(S),3(R)-bis(tert-butyldimethylsilyloxy)-20(S)-formyl-9,10-secopregna-5,7(E),10(19)-triene (112790-51-9,266686-81-1) → (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) + 1(S),3(R)-bis<(tert-butyldimethylsilyl)oxy>-20(R)-formyl-9,10-secopregna-5(E),7(E),10(19)-triene (115648-67-4)

Guidance literature:

With sodium hydrogencarbonate; In ethanol; for 1.5h; Heating;

DOI:10.1016/S0040-4020(01)86903-9

upstream raw materials:

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

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

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

(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

Downstream raw materials:

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

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

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

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