2',3',5'-tri-O-methylsulfonyluridine | 59211-02-8

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 2',3',5'-tri-O-methylsulfonyluridine
• 英文别名: 2',3',5'-tri-O-mesyluridine；O^2'_,O3'_,O5'-tris-methanesulfonyl-uridine；2',3',5'-Tri-O-methansulfonyl-L-uridin；2',3',5'-Tri-O-methylsulfonyluridin；2',3',5'-tri-O-methanesulfonyluridine；[(2R,3R,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-bis(methylsulfonyloxy)oxolan-2-yl]methyl methanesulfonate
• CAS: 59211-02-8
• 化学式: C₁₂H₁₈N₂O₁₂S₃
• 分子量: 478.479
• InChiKey: BRLHWTPRJHLKFO-QCNRFFRDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  214
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  2',3',5'-tri-O-methylsulfonyluridine 在 钯 吡啶 、 sodium hydroxide 、 sodium azide 、 氢气 作用下， 以 1,4-二氧六环 、 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 25.0~100.0 ℃ 、350.0 kPa 条件下， 反应 76.5h， 生成 1-(2-O-acetyl-5-benzamido-3,5-dideoxy-3-diphenylphosphoramido-β-D-arabinofuranosyl)uracil
  参考文献：
  名称：

  Azido-(amino-)furanosyl nucleosides and their phosphoramidates

  摘要：

  The ring-opening of 2,2'-anhydro-1-[5-azido- 5 and 5-benzamido- 3 5-deoxy-3-O-methylsulfonyl-beta-D-arabinofuranosyl] uracil by the ion exchanger Dowex 50 (H+) afforded the corresponding 1-[5-azido-8 and 5-benzamido- 12 5-deoxy-3-O-methylsulfonyl-beta-D-arabinofuranosyl]uracil. Hydrogenolysis of the azido nucleosides over Pd-black in the presence of benzoic acid anhydride led to the corresponding benzamido nucleosides in high yields. The 5'-azido-2',3'-oxirane 10 on reaction with ethanolic ammonia generated 1-(3-amino-5-azido-3,5-dideoxy-beta-D-arabinofuranosyl)uracil 15 and 1-(2-amino-5-azido-2,5-dideoxy-beta-D-xylofuranosyl)uracil 16 in a ratio 2:1. The 5'-O-mesyl-2',3'-oxirane 25, on being treated with NaN3 in DMF at 100-degrees-C, afforded 2',5'-anhydro-1-(3-azido-3-deoxy-beta-D-arabinofuranosyl) uracil 26 (54.5%), 3',5'-diazido-beta-D-arabinofuranosyl 27 (20.6%) and 2',5'-diazido-beta-D-xylofuranosyl 28 (5.4%). The hydrogenolysis of 5 over Pd-black proceeded into 2,5'-imino-1-(3-O-methylsulfonyl-beta-D-arabinofuranosyl)uracil 32 which, as the 5'-benzamido derivative 36, was transformed into 3. The 5'-azido compound 5 and 10 on reaction with triphenyl phosphite in aqueous dioxane gave the respective 5'-diphenylphosphoramidate 38 and 39. Similarly, the 3'-azido compound 22 was converted into 3'-diphenylphosphoramidate 40.

  DOI：

  10.1039/p19920001065
• 作为产物：
  描述：

  甲基磺酰氯 、 尿嘧啶核苷 在 吡啶 作用下， 生成 2',3',5'-tri-O-methylsulfonyluridine
  参考文献：
  名称：

  [d4U]-Spacer-[HI-236] HIV-1 逆转录酶双药抑制剂

  摘要：

  [d4U]-间隔基-[HI-236] 类型的四种双药 HIV NRTI/NNRTI 抑制剂15a – d，其中间隔基变化为 1-丁炔基 ( 15a )、炔丙基-1-PEG ( 15b )、炔丙基-2-PEG ( 15c ) 和炔丙基-4-PEG ( 15d ) 已被合成并作为抗 HIV-1 的 RT 抑制剂进行生物学评估。他们合成的关键步骤涉及 5-碘 d4U 苯甲酸酯与炔基化 HI-236 前体的 Sonogashira 偶联，然后引入 HI-236 硫脲官能团。细胞培养（MT-2 细胞）以及使用体外 RT 测定的生物学评估显示15a – c比 d4T 更活跃。然而，总体而言，结果表明衍生物作为链延长的 NNRTIs，其中对于15b - d，核苷组分可能位于口袋外，但没有证据表明 NRTI 和 NNRTI 位点之间存在任何协同双结合。这部分归因于由于激酶识别失败导致双药核苷组分缺乏磷酸化，而结合

  DOI：

  10.1016/j.bmc.2010.05.025

文献信息

• 2',3'-dideoxy-4-thio-uridine derivatives, process for their preparation
  申请人：Sanyo-Kokusaku Pulp Co., Ltd.

  公开号：US04954485A1

  公开（公告）日：1990-09-04

  2',3'-Dideoxy-4-thio-uridine derivatives represented by a following general formula ##STR1## (wherein R indicates hydrogen or protecting groups such as acetyl group, benzoyl group, trityl groups, etc.), process for their preparation, antivirus agents used them as effective ingredients and therapeutic method and therapeutic drugs for virus diseases are disclosed.

  本发明公开了一种由下列一般式所表示的2'，3'-二脱氧-4-硫代尿嘧啶衍生物：##STR1##（其中R表示氢或保护基，如乙酰基、苯甲酰基、三苯甲基等），以及它们的制备方法、作为有效成分的抗病毒剂、治疗病毒性疾病的治疗方法和治疗药物。
• Minamoto, Katsumaro; Fujiwara, Norio; Hoshino, Yoshihisa, Journal of the Chemical Society. Perkin transactions I, 1990, # 11, p. 3027 - 3033
  作者：Minamoto, Katsumaro、Fujiwara, Norio、Hoshino, Yoshihisa、Hamano, Yuji、Eguchi, Shoji、et al.

  DOI：——

  日期：——
• One-step synthesis of C-2 dialkylamino-substituted 2′,3′-O-anhydro-lyxo-uridines: First report on the opening of 2,2′-O-anhydro-bridge of 2,2′-O-anhydrouridine by secondary amines.
  作者：Kandasamy Sakthivel、Sanjib Bera、Tanmaya Pathak

  DOI：10.1016/s0040-4020(01)80564-0

  日期：1993.1

  Secondary amines successfully opened the 2,2'-O-anhydro-bridge of 2,2'-O-anhydrouridines 8a and 8b in presence of 3'-O-mesyl group to produce compounds 10a-13a and 10b-13b, a new class of isocytidine derivatives.
• MINAMOTO, KATSUMARO;FUJIWARA, NORIO;HOSHINO, YOSHIHISA;HAMANO, YUJI;EGUCH+, J. CHEM. SOC. PERKIN TRANS. PT 1,(1990) N1, C. 3027-3033
  作者：MINAMOTO, KATSUMARO、FUJIWARA, NORIO、HOSHINO, YOSHIHISA、HAMANO, YUJI、EGUCH+

  DOI：——

  日期：——
• MINAMOTO, KATSUMARO;FUJIWARA, NORIO;AZUMA, KISHIKO;EGUCHI, SHOJI, 15TH SYMP. NUCL. ACIDS CHEM., SAPPORO, SEPT. 19TH - 21ST, 1988, OXFORD; W+
  作者：MINAMOTO, KATSUMARO、FUJIWARA, NORIO、AZUMA, KISHIKO、EGUCHI, SHOJI

  DOI：——

  日期：——

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