Model Studies on the Construction of Side Chains for CD Intermediates of Vitamin D

1995 ◽  
Vol 48 (3) ◽  
pp. 663 ◽  
Author(s):  
WA Loughlin ◽  
RK Haynes
Keyword(s):  
Vitamin D ◽  
Phosphine Oxide ◽  
Side Chains ◽  
Diphenylphosphine Oxide ◽  
Model Studies

Application of Horner- Wittig methodology for the synthesis of vitamin D side chains was examined through selected model studies. A requirement for syn or threo α- hydroxy diphenylphosphine oxide intermediates was established. The successful conversion of the model phosphine oxide (7) into the alkene (13), which demonstrates the potential of this method, is described.

scholarly journals Theoretical Study of the Structures of 4-(2,3,5,6-Tetrafluoropyridyl)Diphenylphosphine Oxide and Tris(Pentafluorophenyl)Phosphine Oxide: Why Does the Crystal Structure of (Tetrafluoropyridyl)Diphenylphosphine Oxide Have Two Different P=O Bond Lengths?

Molecules ◽  
2020 ◽  
Vol 25 (12) ◽  
pp. 2778
Author(s):  
Joseph R. Lane ◽  
Graham C. Saunders
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonding ◽  
Phosphine Oxide ◽  
Density Functional ◽  
Lone Pair ◽  
Diphenylphosphine Oxide ◽  
Functional Theory ◽  
Weak Hydrogen Bonding ◽  
Independent Molecules ◽  
The Difference

The crystal structure of 4-(2,3,5,6-tetrafluoropyridyl)diphenylphosphine oxide (1) contains two independent molecules in the asymmetric unit. Although the molecules are virtually identical in all other aspects, the P=O bond distances differ by ca. 0.02 Å. In contrast, although tris(pentafluorophenyl)phosphine oxide (2) has a similar crystal structure, the P=O bond distances of the two independent molecules are identical. To investigate the reason for the difference, a density functional theory study was undertaken. Both structures comprise chains of molecules. The attraction between molecules of 1, which comprises lone pair–π, weak hydrogen bonding and C–H∙∙∙arene interactions, has energies of 70 and 71 kJ mol−1. The attraction between molecules of 2 comprises two lone pair–π interactions, and has energies of 99 and 100 kJ mol−1. There is weak hydrogen bonding between molecules of adjacent chains involving the oxygen atom of 1. For one molecule, this interaction is with a symmetry independent molecule, whereas for the other, it also occurs with a symmetry related molecule. This provides a reason for the difference in P=O distance. This interaction is not possible for 2, and so there is no difference between the P=O distances of 2.

Effect of C2O stereochemistry on the conformational profile of the side chains of vitamin D analogs.

1993 ◽  
Vol 3 (9) ◽  
pp. 1799-1804 ◽  
Author(s):  
M.Mark Midland ◽  
Joaquin Plumet ◽  
William H. Okamura
Keyword(s):  
Vitamin D ◽  
Side Chains ◽  
Vitamin D Analogs

Tuning peripheral group density in ternary phosphine oxide hosts for low-voltage-driven yellow PhOLEDs

2015 ◽  
Vol 3 (26) ◽  
pp. 6709-6716 ◽  
Author(s):  
Jing Li ◽  
Zhensong Zhang ◽  
Chunmiao Han ◽  
Dongxue Ding ◽  
Yi Zhao ◽  
...  
Keyword(s):  
Phosphine Oxide ◽  
Light Emitting Diodes ◽  
Low Voltage ◽  
Organic Light Emitting Diodes ◽  
Diphenylphosphine Oxide ◽  
Light Emitting ◽  
Organic Light ◽  
Host Materials ◽  
Group Density

Fluorene and diphenylphosphine oxide were employed as peripheral groups to construct ternary host materials DBFxPODEFn with benzofuran as a core, which realized the low-voltage-driven efficient yellow phosphorescence organic light-emitting diodes.

A key intermediate for the convenient synthesis of series of vitamin D 3 analogues with modified side chains

2001 ◽  
Vol 42 (44) ◽  
pp. 7815-7817 ◽  
Author(s):  
Yagamare Fall ◽  
Carlos Fernandez ◽  
Victoria González ◽  
Antonio Mouriño
Keyword(s):  
Vitamin D ◽  
Side Chains ◽  
Convenient Synthesis ◽  
Vitamin D 3

Gemini: The 1,25-dihydroxy Vitamin D Analogs with Two Side-Chains

Vitamin D ◽  
2005 ◽  
pp. 1511-1524 ◽  
Author(s):  
MILAN R. USKOKOVIĆ ◽  
HUBERT MAEHR ◽  
SATYANARAYANA G. REDDY ◽  
YAN CHUN LI ◽  
LUCIANO ADORINI ◽  
...  
Keyword(s):  
Vitamin D ◽  
Side Chains ◽  
Vitamin D Analogs

Vitamin D and Click Chemistry. Part 1. A Stereoselective Route to Vitamin D Analogues (VI) with Triazole Rings in Their Side Chains.

ChemInform ◽  
2004 ◽  
Vol 35 (38) ◽  
Author(s):  
Pedro Lois Suarez ◽  
Zoila Gandara ◽  
Generosa Gomez ◽  
Yagamare Fall
Keyword(s):  
Vitamin D ◽  
Click Chemistry ◽  
Side Chains ◽  
Vitamin D Analogues
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