Synthesis of Sphingosines and Cerebrosides

鞘氨醇和脑苷脂的合成

• 批准号: 61570993
• 负责人: NAKAGAWA Masako
• 金额: $ 1.66万
• 依托单位: Chiba University
• 依托单位国家: 日本
• 项目类别: Grant-in-Aid for General Scientific Research (C)
• 财政年份: 1986
• 资助国家: 日本
• 起止时间: 1986 至 1987
• 项目状态: 已结题
• 来源: https://kaken.nii.ac.jp/grant/KAKENHI-PROJECT-61570993/
• 关键词: スフインゴシン; セラミド; セレブロサイド; セレブロサイドBb; ニトロエタノール; アルドール反応; α-ハイドロキシパルミチン酸; (±)-スフインゴシン; ニトロアルコール

1. Synthesis of racemic sphingosine 1, the corresponding ceramide 2, and cerebroside 3 and related compounds were accomplished by newly developed our method for synthesis of aminodiols from the reaction of <alpha>,<beta>-unsaturated aldehydes and nitroethanol.2. As an extension of the above results, the first total synthesis of cerebroside B_<1b>, 4, which was isolated from Tetragonia tetragonoides as a principle withanti-ulcerogenic activity, was succeeded.3. Optically active <alpha>-hydroxypalmitic acid 6 was synthesized by use of oxazolidinone 5.

1. 以< α >,< β >-不饱和醛和硝基乙醇为原料合成氨基二醇的新方法合成了外消旋鞘氨醇1、相应的神经酰胺2、脑苷3及相关化合物。作为上述结果的延伸，首次成功合成了以抗溃疡活性为原则从类四角龙中分离得到的脑苷B_<1b>, 4。以恶唑烷酮5为原料合成了旋光性< α >-羟基铝酸6。

项目成果

Tohru Hino, Kiyoshi Nakayama, Mikio Taniguchi, and Masako Nakagawa: "A New Route to Racemic erythro-Sphingosine and Ceramides. The 1,2-versus 1,4-Addition Reaction of Hexadec-2-enal with 2-Nitroethanol" Jouranl of Chemcal Society, Perkin Trans. 1.1687-169

Tohru Hino、Kiyoshi Nakayama、Mikio Taniguchi 和 Masako Nakakawa：“外消旋赤型鞘氨醇和神经酰胺的新路线。十六进制 2-烯醛与 2-硝基乙醇的 1,2-与 1,4-加成反应”Jouranl of

Tohru Hino: Journal of Chemical Society,Perkin Trans.1. 1687-1690 (1986)

日野彻：化学学会杂志，Perkin Trans.1。

Masako Nakagawa, Shin-ichi Kodato, Kiyoshi Nakayama, Tohru Hino: "Total Synthesis and Determination of Absolute Configuration of Cerebroside B_<1b> and Its Stereoisomers." Tetrahedron Letters. 28. 6281-6284 (1987)

Masako Nakakawa、Shin-ichi Kodato、Kiyoshi Nakayama、Tohru Hino：“脑苷脂 B_<1b> 及其立体异构体的全合成和绝对构型测定”。

Masako Nakagawa: Tetrahedron Letters. 28. 6281-6284 (1987)

中川雅子：四面体字母。

T.Hino;K.Nakayama;M.Taniguchi;M.Nakagawa: Journal ehemical Society,Perkin Transactions I. 1687-1690 (1986)

T.Hino；K.Nakayama；M.Taniguchi；M.Nakakawa：化学学会期刊，Perkin Transactions I. 1687-1690 (1986)