有機合成化学協会誌
Online ISSN : 1883-6526
Print ISSN : 0037-9980
ISSN-L : 0037-9980
細胞内情報伝達に関与するイノシトールリン脂質の全合成と合成手法の開拓
渡辺 裕
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ジャーナル フリー

1997 年 55 巻 8 号 p. 705-713

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Recently, inositol phospholipids in the plasma membrane have received much attention due to their biological interests in signal transduction systems. In order to accomplish efficient syntheses of the target lipids, a selective phosphorylation methodology via phosphonium salt and glycosylation method using glycosyl phosphite as a glycosyl donor were developed based on the phosphite chemistry. New benzoyl derivatives bearing oxyethyl substituents at the ortho position, so called PAC were devised for protecting hydroxyl groups. They can be removed chemoselectively by an intramolecular cyclization mode even in the presence of an acyl group and also function as an auxiliary in the diastereoselective acylation using a monomethyl tartrate derivative. Employing these synthetic strategies, synthesis of phosphatidylinositol 3, 4, 5-trisphosphate, 4, 5-bisphosphate, and 2, 6-dimannopyranosylphosphatidylinositol were achieved in an efficient and concise manner.

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