73367-76-7Relevant articles and documents
2-Diphenylphosphinonyl-acetyl as a Remote Directing Group for the Highly Stereoselective Synthesis of β-Glycosides
Liu, Xianglai,Lin, Yetong,Liu, Ao,Sun, Qianhui,Sun, Huiyong,Xu, Peng,Li, Guolong,Song, Yingying,Xie, Weijia,Sun, Haopeng,Yu, Biao,Li, Wei
supporting information, p. 443 - 452 (2021/12/27)
The configuration of the anomeric glycosidic linkages is crucial for maintaining the biological functions and activities of carbohydrate molecules. However, their stereochemistry control in glycosylation represents one of the most challenging tasks in car
Stereochemically controlled Synthesis of Unsaturated Alcohols by the Horner-Wittig Reaction
Ayrey, Peter M.,Bolton, Michael A.,Buss, Antony D.,Greeves, Nicholas,Levin, Daniel,et al.
, p. 3407 - 3418 (2007/10/02)
Single isomers (E or Z) of unsaturated alcohols with two to five carbon atoms between the double bond and the OH group may be made by the phosphine oxide version of the Horner-Wittig reaction.Hydroxyalkyldiphenylphosphine oxides react with aldehydes either directly or as silyl ethers to give a moderately Z-selective synthesis, while rearrangement of esters of the same alcohols by acyl transfer or acylation of alkyldiphenylphosphine oxides with lactones gives hydroxy ketones whose reduction and elimination leads to an E-selective synthesis.In most cases, separation of the diastereoisomers of the Horner-Wittig intermediates leads to the preparation of pure E- or Z-alkenols.
Novel Synthesis of ω-(Diphenylphosphinyl)alkylcarboxylic Acids from Triphenyl-ω-carboxyalkylphosphonium Salts
Narayanan, Kolazi S.,Berlin, K. Darrell
, p. 2240 - 2243 (2007/10/02)
A novel method for the synthesis of triphenylphosphonium salts of the type (C6H5)3P+(CH2)nCO2H,X- (1: n=2,3; X=Cl; n=5,10,11; X=Br) from the corresponding ω-haloalkylcarboxylic acids and triphenylphosphine has been described.When members of 1 were treated with NaH/Me2SO/THF at room temperature under N2, the corresponding ω-(diphenylphosphinyl)alkylcarboxylic acids 2 (n=3,5,10,11) were isolated.The yields were good (62-75percent) for compounds with longer side chains (n=10,11).In one case (n=3), (C6H5)3P was isolated as a side product (yield 20percent).Attempts to prepare the Wittig reagents from 1 and the subsequent reaction with aldehydes (benzaldehyde and 9-anthraldehyde) failed to yield the expected alkenes.However, members of 2 were produced, and it was possible to recover >90percent of the unreacted 9-anthraldehyde.The structures of the compounds in the series 1 and 2 have been established via the spectral properties and elemental analyses.The 31P and 13C chemical shifts as well as C-P coupling constants have been evaluated and analyzed.A tentative mechanism has been proposed for the formation of 2 from 1.
