Synthetic Route of 4020-99-9. Let’s face it, organic chemistry can seem difficult to learn. Especially from a beginner’s point of view. Like 4020-99-9, Name is Methoxydiphenylphosphine. In a document type is Article, introducing its new discovery.
The benzyl-protected glycosyl acetates 1, 6, 11, and 15 react with MeOPPh2 under catalysis by TMSOTf to yield diastereoselectively the glycosylphosphine oxides 2, 3, 8, 12, 13, and 16, with a strong preference for the 1,2-cis-configurated anomers.Hydrogenolysis of the major products gave the crystalline, unprotected phosphine oxides 4, 9, 14, and 17, of which 4 was transformed into the acetate 5, and 9 into the benzoate 10.The benzylated phosphine oxides 2, 8, 12, and 16 were reduced with Cl3SiH in the presence of a tertiary amine to form the phosphines 18, 21, 24, and 26, which were transformed into the phosphine sulfides 19, 22, 25, and 27.Moreover, 18 and 21 were characterized as the borane adducts 20 and 23.The structure of the (arabinofuranosyl)phosphine oxide 12, the corresponding sulfide 25, and of the borane complex 20 were established by X-ray analysis.According to NMR spectroscopy, the equatorial pyranosylphosphine oxide 8, the sulfide 22, and the borane complex 23 adopt a 4C1 conformation.The axial phosphine oxide 2 is a flattened 4C1, the sulfide 19 exists as B2.5, and the borane complex 20 is a flattened 4C1 in the solid state and a B2.5 in solution.Thus, the conformational behavior of these alpha-D-glucopyranose derivatives reflects the steric requirement of the P-substituents.
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Reference：
Phosphine ligand,
Chiral phosphine ligands in asymmetric synthesis. Molecular structure and absolute configuration of (1,5-cyclooctadiene)-(2S,3S)-2,3-bis(diphenylphosphino)butanerhodium(I) perchlorate tetrahydrofuran solvate