A new protecting group ‘3,5-O-sulfinyl’ for xylo-nucleosides. A simple and efficient synthesis of 3-amino-3-deoxyadenosine (a puromycin intermediate), 2,2-anhydro-pyrimidine nucleosides and 2,3-anhydro-adenosine |
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| Authors: | Ken-ichi Takatsuki Makoto Yamamoto Keiki Kishikawa |
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| Institution: | a Ichikawa Research Institute, Kobayashi Perfumery Co., Ltd., 4-12-1 Ohwada, Ichikawa City 272-0025, Japan
b Department of Specialty Materials Science, Graduate School of Science and Technology, Chiba University, 1-33 Yayoicho, Inageku, Chiba 263-8522, Japan |
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| Abstract: | We developed a new protecting group, the cyclic sulfite for the protection of the 3′,5′-dihydroxy group of nucleosides. Seven cyclic sulfites, 4a-c, 5a-b, and 6a-b were prepared in high yields from the corresponding xylo-uridines 1 and 2, and xylo-adenosines 3 with thionyl chloride, respectively. Synthesis of the puromycin intermediate 8 was carried out by deprotection of the sulfite moiety through an intramolecular cyclization of the 2′-α-carbamate 7. |
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| Keywords: | 3&prime -amino-3&prime -deoxyadenosine 3&prime 5&prime -O-sulfinyl-xylo-nucleosides puromycin |
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