Stereocontrolled Construction of 1,2-cis-.ALPHA.-Glycosidic Linkages Using Glycosyl Diphenyl Phosphates and Synthesis of .ALPHA.-Galactosylceramide KRN7000

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  • グリコシルジフェニルホスファートを用いる１，２－ｃｉｓ－α－グリコシド結合の立体選択的構築とα－ガラクトシルセラミド（ＫＲＮ７０００）の合成
  • グリコシルジフェニルホスファートを用いる1,2-cis-α-グリコシド結合の立体選択的構築とα-ガラクトシルセラミド(KRN7000)の合成[含 英語文]
  • グリコシルジフェニルホスファート オ モチイル 1 2 cis アルファ グリコシド ケツゴウ ノ リッタイ センタクテキ コウチク ト アルファ ガラクトシルセラミド KRN7000 ノ ゴウセイ ガン エイゴブン
  • Stereocontrolled Construction of 1,2-cis-α-Glycosidic Linkages Using Glycosyl Diphenyl Phosphates and Synthesis of α-Galactosylceramide KRN7000

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Abstract

The development of a general stereoselective method for 1,2-cis-α-glycosidations remains an important issue for synthesis in carbohydrate chemistry. Recently, we have achieved a highly stereocontrolled construction of 1,2-cis-α-glycosidic linkages using glycosyl diphenyl phosphates as glycosyl donors. The per-O-benzyl-protected glucosyl and galactosyl donors and the 3,4,6-tri-O-acetyl-2-azido-2-deoxygalactosyl donor each react with a range of acceptor alcohols in the presence of 0.05–0.2 equiv of HClO4 in dioxane/Et2O (1:1) to afford glycosides in good yields with good to high α-selectivities. The synthetic utility of the present glycosidation method was demonstrated by a stereoselective synthesis of the α-galactosylceramide KRN7000, an activator of natural killer (NK) T cells through CD1d molecules.

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