Synthesis of Novel 2,2'-Anhydro-L-threosylpyrimidine Phosphonates

doi:10.6023/cjoc202303015

Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (9): 3167-3173.DOI: 10.6023/cjoc202303015 Previous Articles Next Articles

新型2,2'-缩水-L-苏糖嘧啶膦酸核苷的合成

朱传涛^a, 王松^a, 赵一凡^a, Herdewijn Piet^a^,^c^,^*(), 刘丰五^a^,^b^,^*()

a 郑州大学药物研究院 XNA生物医学研究所郑州 450001
b 郑州大学药物关键制备技术教育部重点实验室郑州 450001
c Medicinal Chemistry, Rega Institute for Medical Research, KU Leuven, Herestraat 49, 3000 Leuven, Belgium

收稿日期:2023-03-10 修回日期:2023-05-05 发布日期:2023-06-13

Synthesis of Novel 2,2'-Anhydro-L-threosylpyrimidine Phosphonates

Chuantao Zhu^a, Song Wang^a, Yifan Zhao^a, Piet Herdewijn^a^,^c(), Fengwu Liu^a^,^b()

a XNA Platform, Institute of Pharmaceutical Sciences, Zhengzhou University, Zhengzhou 450001
b Key Laboratory of Advanced Drug Preparation Technologies, Ministry of Education, Zhengzhou University, Zhengzhou 450001
c Medicinal Chemistry, Rega Institute for Medical Research, KU Leuven, Herestraat 49, 3000, Leuven

Received:2023-03-10 Revised:2023-05-05 Published:2023-06-13
Contact: * E-mail: fwliu@zzu.edu.cn;piet.herdewijn@kuleuven.be

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Abstract

A series of L-threoylnucleoside phosphonates were synthesized via a nine-step procedure firstly. When the L-threoylpyrimidine nucleoside phosphonate was treated by diethylaminosulphur trifluoride (DAST), all the tried pyrimidine L-threosylnucleoside phosphonate analogues produced corresponding 2,2'-anhydro-1-(L-threoyl)pyrimidine phosphonates in medium-high yields. The obtained L-threoylpyrimidine nucleoside phosphonates and 2,2'-anhydro-L-threosylpyrimidine phosphonic acids have not shown any activity by primary biological evaluations.

Key words: 2,2'-anhydronucleoside, diethylaminosulphur trifluoride (DAST), L-threosylpyrimidine phosphonate

Cite this article

Chuantao Zhu, Song Wang, Yifan Zhao, Piet Herdewijn, Fengwu Liu. Synthesis of Novel 2,2'-Anhydro-L-threosylpyrimidine Phosphonates[J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3167-3173.

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Fig. & Tab. 3

Scheme 1. Synthesis of 3'-O-phosphonate L-threosyluridines from D-xylose Reagents and conditions: (i) acetone, H2SO4, 0 ℃~r.t.; (ii) N-hydroxyphthalimide, PPh3, DEAD, THF; (iii) Bu3SnH, AIBN, toluene, 80 ℃; (iv) diethyl p-tosyloxymethylphosphonate, NaH, THF, 0 ℃~r.t.; (v) MeOH, H2SO4, 0 ℃~r.t.; (vi) BzCl, pyridine, 0 ℃~r.t.; (vii) AcOH, Ac2O, H2SO4; (viii) base, BSA, CH3CN, TMSOTf; (ix) NH3/MeOH, r.t.

Scheme 2. Formation of 2,2'-anhydro-L-threonucleoside analo- gues

Scheme 3. Synthesis of compounds 12

References 21

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新型2,2'-缩水-L-苏糖嘧啶膦酸核苷的合成

Synthesis of Novel 2,2'-Anhydro-L-threosylpyrimidine Phosphonates

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