2,2-Dimethyl-propionic acid (S)-3-hydroxy-2-(toluene-4-sulfonyloxy)-propyl ester | 615250-59-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,2-Dimethyl-propionic acid (S)-3-hydroxy-2-(toluene-4-sulfonyloxy)-propyl ester
• 英文别名: [(2S)-3-hydroxy-2-(4-methylphenyl)sulfonyloxypropyl] 2,2-dimethylpropanoate
• CAS: 615250-59-4
• 化学式: C₁₅H₂₂O₆S
• 分子量: 330.402
• InChiKey: AKVZXCUWIBWLDE-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  98.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3S,4R)-6-acetoxy-4-dimethylamino-2-methyl-tetrahydro-pyran-3-yl ester 、 2,2-Dimethyl-propionic acid (S)-3-hydroxy-2-(toluene-4-sulfonyloxy)-propyl ester 在 molecular sieve 、 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 2,2-Dimethyl-propionic acid (S)-3-((2R,4R,5S,6R)-5-acetoxy-4-dimethylamino-6-methyl-tetrahydro-pyran-2-yloxy)-2-(toluene-4-sulfonyloxy)-propyl ester 、 2,2-Dimethyl-propionic acid (S)-3-((2S,4R,5S,6R)-5-acetoxy-4-dimethylamino-6-methyl-tetrahydro-pyran-2-yloxy)-2-(toluene-4-sulfonyloxy)-propyl ester
  参考文献：
  名称：

  Glycidol-carbohydrate hybrids: a new family of DNA alkylating agents

  摘要：

  Novel and chiral glycidol-carbohydrate hybrids possessing an epoxy group as a DNA alkylating moiety were designed and synthesized. These artificial hybrids selectively alkylated DNA at the N-7 sites of the guanines and cleaved DNA without any additives. The binding ability of the glycidol was significantly enhanced by the attachment of the carbohydrate. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00659-0
• 作为产物：
  描述：

  2,2-Dimethyl-propionic acid (R)-3-(tert-butyl-diphenyl-silanyloxy)-2-(toluene-4-sulfonyloxy)-propyl ester 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以72%的产率得到2,2-Dimethyl-propionic acid (S)-3-hydroxy-2-(toluene-4-sulfonyloxy)-propyl ester
  参考文献：
  名称：

  Glycidol-carbohydrate hybrids: a new family of DNA alkylating agents

  摘要：

  Novel and chiral glycidol-carbohydrate hybrids possessing an epoxy group as a DNA alkylating moiety were designed and synthesized. These artificial hybrids selectively alkylated DNA at the N-7 sites of the guanines and cleaved DNA without any additives. The binding ability of the glycidol was significantly enhanced by the attachment of the carbohydrate. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00659-0

文献信息

• Glycidol-carbohydrate hybrids: a new family of DNA alkylating agents
  作者：Kazunobu Toshima、Yukiko Okuno、Shuichi Matsumura

  DOI：10.1016/s0960-894x(03)00659-0

  日期：2003.10

  Novel and chiral glycidol-carbohydrate hybrids possessing an epoxy group as a DNA alkylating moiety were designed and synthesized. These artificial hybrids selectively alkylated DNA at the N-7 sites of the guanines and cleaved DNA without any additives. The binding ability of the glycidol was significantly enhanced by the attachment of the carbohydrate. (C) 2003 Elsevier Ltd. All rights reserved.