toluene-4-sulfonic acid 2-(2,2-diethyl[1,3]dioxolan-4-yl)ethyl ester | 336883-67-1

• 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: toluene-4-sulfonic acid 2-(2,2-diethyl[1,3]dioxolan-4-yl)ethyl ester
• 英文别名: (+/-)-(S)-4-tosyloxy-1,2-O-3-pentylidene-1,2-butanediol；2-(2,2-Diethyl-1,3-dioxolan-4-yl)ethyl 4-methylbenzenesulfonate
• CAS: 336883-67-1
• 化学式: C₁₆H₂₄O₅S
• 分子量: 328.43
• InChiKey: ZTCCOSNVWILNDQ-UHFFFAOYSA-N

物化性质

• 沸点：
  438.1±25.0 °C(Predicted)
• 密度：
  1.129±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  70.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  toluene-4-sulfonic acid 2-(2,2-diethyl[1,3]dioxolan-4-yl)ethyl ester 在 四丁基氟化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 (2S,4S,5R,6R)-5-Acetylamino-6-[(S)-[2-(2,2-diethyl-[1,3]dioxolan-4-yl)-ethoxy]-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-4-hydroxy-2-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis and anti-influenza evaluation of orally active bicyclic ether derivatives related to zanamivir

  摘要：

  We synthesized bicyclic ether sialidase inhibitors Such as tetrahydro-furan-2-yl. tetrahydro-pyran-2-yL and oxepan-2-yl derivatives related to zanamivir. These compounds substituted by diol at the C-3' and C-4' positions resulted in the retention of low nanomolar inhibitory activities against not only influenza A virus sialidase but also influenza A virus in cell culture. Compound I la in particular showed comparable efficacy in vivo relative to that of oseltamivir phosphate. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)01039-9
• 作为产物：
  描述：

  3,3-dimethoxypentane 在 吡啶 、 对甲苯磺酸 作用下， 生成 toluene-4-sulfonic acid 2-(2,2-diethyl[1,3]dioxolan-4-yl)ethyl ester
  参考文献：
  名称：

  Synthesis and anti-influenza evaluation of orally active bicyclic ether derivatives related to zanamivir

  摘要：

  We synthesized bicyclic ether sialidase inhibitors Such as tetrahydro-furan-2-yl. tetrahydro-pyran-2-yL and oxepan-2-yl derivatives related to zanamivir. These compounds substituted by diol at the C-3' and C-4' positions resulted in the retention of low nanomolar inhibitory activities against not only influenza A virus sialidase but also influenza A virus in cell culture. Compound I la in particular showed comparable efficacy in vivo relative to that of oseltamivir phosphate. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)01039-9

文献信息

• Total Synthesis of (−)-Cylindricine C
  作者：Gary A. Molander、Magnus Rönn

  DOI：10.1021/jo990363l

  日期：1999.7.1

  (-)-Cylindricine C has been synthesized from commercially available (S)-(-)-1,2,4-butanetriol in 11 steps with an overall yield of 12%. The key step utilizes a CrCl2 reduction of an azide to form the corresponding amine with a subsequent double Michael addition to create the tricyclic skeleton of cylindricine from a monocyclic substrate.

  (-)-Cylindricine C 通过从商购的 (S)-(-)-1,2,4-butanetriol 开始，在 11 步反应中成功合成，总产率为 12%。关键步骤采用了 CrCl₂ 还原叠氮化物以生成相应的胺，随后进行双迈克尔加成，以从单环底物中构建 cylindricine 的三环骨架。
• Cyclization Strategies for the Synthesis of Macrocyclic Bisindolylmaleimides
  作者：Margaret M. Faul、Christine A. Krumrich

  DOI：10.1021/jo001605g

  日期：2001.3.1

  Three new approaches to the synthesis of macrocyclic bisindolylmaleimides 1-4 have been identified. Two strategies afford 8, the penultimate intermediate for the synthesis of 1-4, in 73% and 32% yield by intramolecular cyclization of 31 and 40, respectively. The optimum synthesis of 1 was achieved in nine steps and 15% yield by intramolecular formation of the macrocycle and maleimide in one step by reaction of the sodium indolate of 12 with methyl indole-3-glyoxylate 47. The mechanism of this reaction has been elucidated, using the trityl-protected derivative, to involve initial formation of the tricarbonyl im ide 48, followed by irreversible alkylation of the indole nitrogen to generate the 17-membered macrocycle 49. Cyclization of 49 to hydroxymaleimide 50 and subsequent dehydration afforded 8a. This approach eliminated the problem of dimerization observed in the intramolecular cyclization reactions.
• J. Org. Chem. 2001, 66, 2024-2033
  作者：

  DOI：——

  日期：——
• Synthesis and anti-influenza evaluation of orally active bicyclic ether derivatives related to zanamivir
  作者：Takeshi Masuda、Satoshi Shibuya、Masami Arai、Shuku Yoshida、Takanori Tomozawa、Akiko Ohno、Makoto Yamashita、Takeshi Honda

  DOI：10.1016/s0960-894x(02)01039-9

  日期：2003.2

  We synthesized bicyclic ether sialidase inhibitors Such as tetrahydro-furan-2-yl. tetrahydro-pyran-2-yL and oxepan-2-yl derivatives related to zanamivir. These compounds substituted by diol at the C-3' and C-4' positions resulted in the retention of low nanomolar inhibitory activities against not only influenza A virus sialidase but also influenza A virus in cell culture. Compound I la in particular showed comparable efficacy in vivo relative to that of oseltamivir phosphate. (C) 2003 Elsevier Science Ltd. All rights reserved.