[(2R,3S,5R)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)-2-(trityloxymethyl)oxolan-3-yl] 2-[(2R,3S,5R)-3-azido-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]ethanesulfonate | 141089-62-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: [(2R,3S,5R)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)-2-(trityloxymethyl)oxolan-3-yl] 2-[(2R,3S,5R)-3-azido-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]ethanesulfonate
• CAS: 141089-62-5
• 化学式: C₄₀H₄₁N₇O₁₀S
• 分子量: 811.872
• InChiKey: OKPKMCAGYXWCHU-ZWDQFWLOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  58
• 可旋转键数：
  14
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  193
• 氢给体数：
  2
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  [(2R,3S,5R)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)-2-(trityloxymethyl)oxolan-3-yl] 2-[(2R,3S,5R)-3-azido-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]ethanesulfonate 在 silica gel 、 三氟乙酸 作用下， 以 甲醇 、 氯仿 为溶剂， 以81%的产率得到2-[(2R,3S,5R)-3-Azido-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-ethanesulfonic acid (2R,3S,5R)-2-hydroxymethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester
  参考文献：
  名称：

  A facile method for deprotection of trityl ethers using column chromatography

  摘要：

  A mild, efficient and inexpensive detritylation method is reported that uses trifluoroacetic acid on a silica gel column to obtain pure, detritylated compounds in one-step. This method is applicable to acid stable as well as acid sensitive compounds with only slight alterations in the procedure. Nineteen examples are given. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01645-8
• 作为产物：
  描述：

  在 三光气 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 17.0h， 生成 [(2R,3S,5R)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)-2-(trityloxymethyl)oxolan-3-yl] 2-[(2R,3S,5R)-3-azido-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]ethanesulfonate
  参考文献：
  名称：

  Synthesis of thymidine dimers containing internucleoside sulfonate and sulfonamide linkages

  摘要：

  Novel chemistry is reported for the formation of internucleoside sulfonate and sulfonamide linkages.

  DOI：

  10.1021/jo00037a003

文献信息

• A facile method for deprotection of trityl ethers using column chromatography
  作者：Ashish K Pathak、Vibha Pathak、Lainne E Seitz、Kamal N Tiwari、Mohammad S Akhtar、Robert C Reynolds

  DOI：10.1016/s0040-4039(01)01645-8

  日期：2001.10

  A mild, efficient and inexpensive detritylation method is reported that uses trifluoroacetic acid on a silica gel column to obtain pure, detritylated compounds in one-step. This method is applicable to acid stable as well as acid sensitive compounds with only slight alterations in the procedure. Nineteen examples are given. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Synthesis of thymidine dimers containing internucleoside sulfonate and sulfonamide linkages
  作者：Robert C. Reynolds、Peter A. Crooks、Joseph A. Maddry、M. Shamim Akhtar、John A. Montgomery、John A. Secrist

  DOI：10.1021/jo00037a003

  日期：1992.5

  Novel chemistry is reported for the formation of internucleoside sulfonate and sulfonamide linkages.