N³-(4-methylbenzoyl)-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)uridine | 108782-95-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N³-(4-methylbenzoyl)-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)uridine
• 英文别名: N³-p-toluyl-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)uridine；1-[(6aR,8R,9R,9aS)-9-hydroxy-2,2,4,4-tetra(propan-2-yl)-6a,8,9,9a-tetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl]-3-(4-methylbenzoyl)pyrimidine-2,4-dione
• CAS: 108782-95-2
• 化学式: C₂₉H₄₄N₂O₈Si₂
• 分子量: 604.848
• InChiKey: OWOXRGSKMXKZPR-GTVIQNQPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.22
• 重原子数：
  41
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  115
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N³-(4-methylbenzoyl)-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)uridine 在 四丁基氟化铵 、 苯磺酸 作用下， 以 吡啶 为溶剂， 生成 4-{(2R,3R,4R,5R)-4-Hydroxy-2-[3-(4-methyl-benzoyl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-5-[9-(4-octadecyloxy-phenyl)-9H-xanthen-9-yloxymethyl]-tetrahydro-furan-3-yloxy}-4-methoxy-heptanedioic acid dimethyl ester
  参考文献：
  名称：

  Site-specific modification of the pyrimidine residue during the deprotection of the fully-protected diuridylic acid

  摘要：

  DOI：

  10.1016/s0040-4020(01)88067-4
• 作为产物：
  描述：

  3',5'-O-(1,1,3,3-四异丙基-1,3-二硅氧烷)尿苷 在 四丁基溴化铵 、 sodium carbonate 作用下， 以 二氯甲烷 、 水 、 1,2-二氯乙烷 为溶剂， 反应 0.25h， 生成 N³-(4-methylbenzoyl)-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)uridine
  参考文献：
  名称：

  A New Microfluidic Phase-Transfer Reaction Using HPLC Guard Columns as the Reactor for the N3-Protection of Uridine Derivatives

  摘要：

  N-3-Acylation of uridine derivatives with acyl chlorides, mediated by a phase-transfer reaction, was studied using a new microfluidic device containing an HPLC guard as an effective reactor. The acylated products were obtained in more than 80% yields in very short reaction times of several seconds.

  DOI：

  10.1055/s-0035-1560264

文献信息

• General method for the preparation of N3- and O4-substituted uridine derivatives by phase-transfer reactions
  作者：Mitsuo Sekine

  DOI：10.1021/jo00271a015

  日期：1989.5
• SEKINE, MITSUO, J. ORG. CHEM., 54,(1989) N0, C. 2321-2326
  作者：SEKINE, MITSUO

  DOI：——

  日期：——
• Site-specific modification of the pyrimidine residue during the deprotection of the fully-protected diuridylic acid
  作者：X-X. Zhou、J. Chattopadhyaya

  DOI：10.1016/s0040-4020(01)88067-4

  日期：1986.1
• A New Microfluidic Phase-Transfer Reaction Using HPLC Guard Columns as the Reactor for the N3-Protection of Uridine Derivatives
  作者：Kohji Seio、Mitsuo Sekine、Nobuhiro Tago、Yoshiaki Masaki、Hiroshi Nagasawa、Takashi Kanamori、Akihiro Ohkubo

  DOI：10.1055/s-0035-1560264

  日期：——

  N-3-Acylation of uridine derivatives with acyl chlorides, mediated by a phase-transfer reaction, was studied using a new microfluidic device containing an HPLC guard as an effective reactor. The acylated products were obtained in more than 80% yields in very short reaction times of several seconds.