Synthesis of 5-methyl-19-nor-5β-pregn-9-ene derivatives

1990 ◽  
Vol 55 (7) ◽  
pp. 1783-1791 ◽  
Author(s):  
Jiří Polman ◽  
Alexander Kasal
Keyword(s):  
Tributyltin Hydride ◽  
Progesterone Analogues

3β,5,6β-Trihydroxy-5α-pregnan-20-one 3-pivalate (I) was converted into 3β,6β-dihydroxy-5-methyl-19-nor-5β-pregn-9-en-20-one 3-pivalate 5-acetate (II) under conditions of Westphalen rearrangement. Deoxygenation in the position 6β was effected by treatment of the corresponding 6β-thiobenzoate or thioimidazolide with tributyltin hydride. Progesterone analogues XII and XIII, prepared from the 6-deoxy compound IX, exhibit abortive activity.

scholarly journals Synthesis and Antiproliferative Evaluation of 2-Deoxy-N-glycosylbenzotriazoles/imidazoles

Molecules ◽  
2021 ◽  
Vol 26 (12) ◽  
pp. 3742
Author(s):  
Caleigh S. Garton ◽  
Noelle K. DeRose ◽  
Dylan Dominguez ◽  
Maria L. Turbi-Henderson ◽  
Ashley L. Lehr ◽  
...  
Keyword(s):  
Cell Lines ◽  
Cancer Cell ◽  
Addition Reaction ◽  
Protecting Group ◽  
Human Breast ◽  
Lung Cancer Cell ◽  
Subsequent Removal ◽  
Anticancer Properties ◽  
Tributyltin Hydride ◽  
High Yields

A series of 2-deoxy-2-iodo-α-d-mannopyranosylbenzotriazoles was synthesized using the benzyl, 4,6-benzylidene and acetyl protected D-glucal in the presence of N-iodosuccinimide (NIS). Subsequent removal of the iodine at the C-2 position using tributyltin hydride under free radical conditions afforded the 2-deoxy-α-d-glucopyranosylbenzotriazoles in moderate to high yields. This method was extended to the preparation of substituted 2-deoxy-β-d-glucopyranosylimidazoles as well. The stereoselectivity of the addition reaction and the effect of the protecting group and temperature on anomer distribution of the benzotriazole series were also investigated. The anticancer properties of the newly synthesized compounds were evaluated in a series of viability studies using HeLa (human cervical adenocarcinoma), human breast and lung cancer cell lines. The N-[3,4,6-tri-O-benzyl-2-deoxy-α-d-glucopyranosyl]-1H-benzotriazole and the N-[3,4,6-tri-O-acetyl-2-deoxy-α-d-glucopyranosyl]-2H-benzotriazole were found to be the most potent cancer cell inhibitors at 20 µM concentrations across all four cell lines.

scholarly journals The Reduction of Chlorodeoxy Sugars by Tributyltin Hydride

1972 ◽  
Vol 45 (2) ◽  
pp. 567-569 ◽  
Author(s):  
Hitoshi Arita ◽  
Nobuhiko Ueda ◽  
Yoshio Matsushima
Keyword(s):  
Tributyltin Hydride

Synthesis of podophyllotoxin derivatives by means of tributyltin hydride- or palladium-mediated cyclization of α-benzylidene-β-(o-bromobenzyl)-γ-lactones

Tetrahedron ◽  
1993 ◽  
Vol 49 (20) ◽  
pp. 4173-4182 ◽  
Author(s):  
Hiroyuki Ishibashi ◽  
Katsuhiro Ito ◽  
Tomiya Hirano ◽  
Masayo Tabuchi ◽  
Masazumi Ikeda
Keyword(s):  
Tributyltin Hydride ◽  
Podophyllotoxin Derivatives

ChemInform Abstract: Reduction of Aldehyde with Tributyltin Hydride-HMPA Combined System.

ChemInform ◽  
1989 ◽  
Vol 20 (48) ◽  
Author(s):  
I. SHIBATA ◽  
T. YOSHIDA ◽  
A. BABA ◽  
H. MATSUDA
Keyword(s):  
Combined System ◽  
Tributyltin Hydride

Organometallic oxides: preparation of the cluster [(η-C5Me5)Mo]4O7 by reduction of [(η-C5Me5)MoCl(O)]2(μ-O) or (η-C5Me5)MoCl2(O)

2000 ◽  
Vol 78 (3) ◽  
pp. 383-394
Author(s):  
Frank Bottomley ◽  
Victor Sanchez ◽  
Robert C Thompson ◽  
Olusola O Womiloju ◽  
Zhiqiang Xu
Keyword(s):  
Nmr Spectra ◽  
Chloroform Solution ◽  
X Ray Diffraction ◽  
Broad Resonance ◽  
Nmr Spectrum ◽  
X Ray ◽  
Temperature Range ◽  
H Nmr ◽  
Tributyltin Hydride ◽  
Effective Moment

Reduction of [(η-C5Me5)MoCl(O)]2(μ-O) or (η-C5Me5)MoCl2(O) with sodium or magnesium amalgam, magnesium turnings, or tributyltin hydride produced [(η-C5Me5)Mo]4O7, with [(η-C5Me5)Mo(O)(μ-O)]2 as a co-product. [(η-C5Me5)Mo]4O7 was characterized by X-ray diffraction, mass spectrometry, 1H NMR and IR spectroscopies, and magnetism. Crystals of [(η-C5Me5)Mo]4O7 contained a tetrahedral [(η-C5Me5)Mo]4 unit (Mo-Mo = 2.909 (3) Å) with the Mo4O7 core having the structure Mo4(μ2-O(b))3(µ2-O(c))3(µ3-O(a)) (3). Microcrystalline samples of [(η-C5Me5)Mo]4O7 were paramagnetic over the temperature range 2-300 K, with an effective moment of 1.26 μB at 300 K. [(η-C5Me5)Mo]4O7 was also paramagnetic in chloroform solution, over the temperature range 223-298 K, with an effective moment of 1.43 µB at 298 K. The 1H NMR spectrum showed a broad resonance at 16.3 ppm (Δν 1/2 = 113 Hz) and two narrow resonances at 1.89 ppm and 1.69 ppm (Δν 1/2 = 5 Hz). The magnetism and NMR spectra showed that [(η-C5Me5)Mo]4O7 existed in two forms which were in equilibrium in solution. One form was paramagnetic (S = 1), with the Mo4O7 core having the geometry 3, and the other was diamagnetic (S = 0), with the Mo4O7 core having the geometry 4.Key words: cluster, cyclopentadienyl, molybdenum, oxide, paramagnetism.

Desulfonylation of Amides using Tributyltin Hydride, Samarium Diiodide or Zinc/Titanium Tetrachloride. A Comparison of Methods

Tetrahedron ◽  
2000 ◽  
Vol 56 (7) ◽  
pp. 979-988 ◽  
Author(s):  
Haydn S Knowles ◽  
Andrew F Parsons ◽  
Robert M Pettifer ◽  
Stéphane Rickling
Keyword(s):  
Titanium Tetrachloride ◽  
Samarium Diiodide ◽  
Comparison Of Methods ◽  
Tributyltin Hydride
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