Specific Effects of 4-Morpholine-N,N'-dicyclohexylcarboxamidine as a Catalyst for the Alkylation and Phosphorylation of Ribonucleosides by a Two-step Phosphorylating Agent, MTBO : Its Application to the Synthesis of Cytokinin-like Nucleotides(Organic Chem

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概要

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• An examination of amines as catalysts for the first-step phosphorylation of nucleosides by a two-step phosphorylating agent, 2-methylthio-4H-1,3,2-benzodioxaphosphorin 2-oxide (MTBO,2), revealed that, in the presence of 4-morpholine-N,N'-dicyclohexylcarboxamidine (MDC,3) as the catalyst, MTBO phosphorylates and o-hydroxybenzylates adenosine borate complex (1) to give 1-(o-hydroxybenzyl)adenosine 5'-S-methyl phosphorothiolate (5), with subsequent Dimroth rearrangement to give N^6-(o-hydroxybenzyl)adenosine 5'-S-methyl phosphorothiolate (6). The guanosine borate complex (7) gave 1-(o-hydroxybenzyl)guanosine 5'-S-methyl phosphorothiolate (8) under the same conditions. MTBO phosphorylated N^6-benzyladenosine and N^6-allyladenosine borate complexes (9a and b) in the presence of n-propylamine (11) to give their 5'-S-methyl phosphorothiolates (10a and b), respectively. Thus, the 5'-S-methyl phosphorothiolates of cytokinin-like nucleosides were synthesized by the use of different amine catalysts from both intact and N^6-substituted nucleosides.

• 社団法人日本農芸化学会の論文
• 1991-08-23

著者

• IIO Masayoshi

  Department of Bioscience and Biotechnology, Faculty of Agriculture, Graduate School, Kyushu Universi

• Iio Masayoshi

  Department Of Food And Nutrition Sciences Kumamoto Women's University

• OMURA Hirohisa

  Department of Food Science and Technology, Faculty of Agriculture, Kyushu University

• ETO Masayoshi

  Laboratory of Food Chemistry, Himeji College of Hyogo

• ETO Morifusa

  Faculty of Agriculture, Kyushu University

• Eto Morifusa

  Faculty Of Agriculture Kyushu University

• Eto Masayoshi

  Laboratory Of Food Chemistry Himeji College Of Hyogo

• Omura Hirohisa

  Department Of Food And Nutrition Nakamura-gakuen College

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