N(3)-BOM uridine | 186839-90-7

• 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: N(3)-BOM uridine
• 英文别名: 3-[(benzyloxy)methyl]-1-(β-D-ribofuranosyl)uracil；1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3-(phenylmethoxymethyl)pyrimidine-2,4-dione
• CAS: 186839-90-7
• 化学式: C₁₇H₂₀N₂O₇
• 分子量: 364.355
• InChiKey: AFORILMLXDCGDS-DTZQCDIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  120
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N(3)-BOM uridine 在 palladium on activated charcoal 咪唑 、 sodium tetrahydroborate 、 氢气 、 sodium hydride 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 9.0h， 生成 3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-2'-O-(2-hydroxyethyl)uridine
  参考文献：
  名称：

  Synthesis of HyBeacons and dual-labelled probes containing 2′-fluorescent groups for use in genetic analysis

  摘要：

  一种受 FMOC 保护的 2â²-羟乙基尿嘧啶磷酰胺被用于合成荧光素标记的 HyBeacon 探针和âFAM-ROXâ双标记荧光寡核苷酸。

  DOI：

  10.1039/b302855k
• 作为产物：
  描述：

  苄基氯甲基醚 、 尿嘧啶核苷 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以93%的产率得到N(3)-BOM uridine
  参考文献：
  名称：

  Nucleosides and Nucleotides. 163. Synthesis of 3‘-β-Branched Uridine Derivatives via Intramolecular Reformatsky-Type Reaction Promoted by Samarium Diiodide¹

  摘要：

  A novel efficient method for the synthesis of 3'-beta-branched uridines starting from uridine was developed, in which a SmI2-promoted intramolecular Reformatsky-type reaction was effectively used. 5'-O-(Bromoacetyl)-3'-ketouridine derivatives 12, 26, and 27 were synthesized from uridine and were subjected to an intramolecular Reformatsky-type reaction. When 12, 26, and 27 were treated with 2.0 equiv of SmI2 in THF at -78 degrees C, intramolecular carbon-carbon bond formation at the 3'-beta-position proceeded smoothly to give the corresponding 3',5'-lactones 14, 28, and 29 in high yields, respectively. Treatment of 28 with NH3/MeOH gave the 3'-beta-branched uridine derivative 32 quantitatively, which was then deprotected to give 3'-C-(carbamoylmethyl)uridine (33).

  DOI：

  10.1021/jo961665f

文献信息

• (2,6-Dichloro-4-alkoxyphenyl)-(2,4-dichlorophenyl)methyl Trichloroacet­imidates: Protection of Alcohols and Carboxylic Acids in Solution or on Polymer Support
  作者：Michio Kurosu、Kai Li

  DOI：10.1055/s-0029-1216974

  日期：2009.11

  (10˜100 mol%) to react with alcohols and carboxylic acids­. Under these conditions a wide variety of alcohols can be transformed into the corresponding ethers in excellent yields with a slight excess of the trichloroacetimidate. The resulting ethers are not susceptible to typical deprotection conditions for benzyl and 4-methoxybenzyl ether groups, however, they can be conveniently deprotected by treatment

  （2，6-二氯-4-甲氧基苯基）-（2，4-二氯苯基）-甲基三氯乙酰亚胺酸酯可以被TMSOTf（10〜100mol％）有效地活化以与醇和羧酸反应。在这些条件下，各种醇可以以极高的收率转化为相应的醚，而三氯乙酰亚氨酸酯略有过量。所得的醚对于典型的苄基和4-甲氧基苄基醚基的脱保护条件不敏感，但是，它们可以通过用在二氯甲烷中的30〜50％三氟乙酸处理而方便地脱保护。聚合物结合的（2,6-二氯-4-烷氧基苯基）-（2,4-二氯苯基）甲基三氯乙酰亚胺酸酯可用于固定醇和羧酸。 保护基-醇和羧酸-二苯甲基酯衍生物-聚合物键合-接头
• Concise Synthesis of Capuramycin
  作者：Michio Kurosu、Kai Li、Dean C. Crick

  DOI：10.1021/ol900458w

  日期：2009.6.4

  A concise total synthesis of capuramycin (1), a promising preclinical TB drug lead, is achieved by high-yield formations of the cyanohydrin 5a and 4 '',5 ''-glycal derivative 12. Capuramycin can be synthesized in eight steps from the uridine building block 5a with >30% overall yield. The synthetic intermediates reported here are useful for generation of analogs to improve pharmacokinetic properties of capuramycin.
• DPAGT1 Inhibitors of Capuramycin Analogues and Their Antimigratory Activities of Solid Tumors
  作者：Katsuhiko Mitachi、Rita G. Kansal、Kirk E. Hevener、Cody D. Gillman、Syed M. Hussain、Hyun Gi Yun、Gustavo A. Miranda-Carboni、Evan S. Glazer、William M. Clemons、Michio Kurosu

  DOI：10.1021/acs.jmedchem.0c00545

  日期：2020.10.8

  Capuramycin displays a narrow spectrum of antibacterial activity by targeting bacterial translocase I (MraY). In our program of development of new N-acetylglucosaminephosphotransferase1 (DPAGT1) inhibitors, we have identified that a capuramycin phenoxypiperidinylbenzylamide analogue (CPPB) inhibits DPAGT1 enzyme with an IC50 value of 200 nM. Despite a strong DPAGT1 inhibitory activity, CPPB does not show cytotoxicity against normal cells and a series of cancer cell lines. However, CPPB inhibits migrations of several solid cancers including pancreatic cancers that require high DPAGT1 expression in order for tumor progression. DPAGT1 inhibition by CPPB leads to a reduced expression level of Snail but does not reduce E-cadherin expression level at the IC50 (DPAGT1) concentration. CPPB displays a strong synergistic effect with paclitaxel against growthinhibitory action of a patient-derived pancreatic adenocarcinoma, PD002: paclitaxel (IC50: 1.25 mu M) inhibits growth of PD002 at 0.0024-0.16 mu M in combination with 0.10-2.0 mu M CPPB (IC50: 35 mu M).
• Synthetic Studies towards the Identification of Novel Capuramycin Analogs with Mycobactericidal Activity
  作者：Michio Kurosu、Kai Li

  DOI：10.3987/com-08-s(f)38

  日期：——

  Expeditious syntheses of capuramycin, an effective MraY inhibitor in vivo, analogs are described. Synthetic schemes reported here are extremely useful for the generation of capuramycin analogs to identify minimum structure requirement to exhibit antimycobactericidal activity.
• Nucleosides and Nucleotides. 163. Synthesis of 3‘-β-Branched Uridine Derivatives via Intramolecular Reformatsky-Type Reaction Promoted by Samarium Diiodide¹
  作者：Satoshi Ichikawa、Satoshi Shuto、Noriaki Minakawa、Akira Matsuda

  DOI：10.1021/jo961665f

  日期：1997.3.1

  A novel efficient method for the synthesis of 3'-beta-branched uridines starting from uridine was developed, in which a SmI2-promoted intramolecular Reformatsky-type reaction was effectively used. 5'-O-(Bromoacetyl)-3'-ketouridine derivatives 12, 26, and 27 were synthesized from uridine and were subjected to an intramolecular Reformatsky-type reaction. When 12, 26, and 27 were treated with 2.0 equiv of SmI2 in THF at -78 degrees C, intramolecular carbon-carbon bond formation at the 3'-beta-position proceeded smoothly to give the corresponding 3',5'-lactones 14, 28, and 29 in high yields, respectively. Treatment of 28 with NH3/MeOH gave the 3'-beta-branched uridine derivative 32 quantitatively, which was then deprotected to give 3'-C-(carbamoylmethyl)uridine (33).