5-tert-butoxycarbonylamino-5-hydroxymethyl-2-phenyl-1,3-dioxane | 154627-61-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二恶烷
• 英文名称: 5-tert-butoxycarbonylamino-5-hydroxymethyl-2-phenyl-1,3-dioxane
• CAS: 154627-61-9
• 化学式: C₁₆H₂₃NO₅
• 分子量: 309.362
• InChiKey: QDZHRDPMCCTUIW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.99
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  77.02
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  5-tert-butoxycarbonylamino-5-hydroxymethyl-2-phenyl-1,3-dioxane 在 草酰氯 、 palladium 10% on activated carbon 、 氢气 、 二甲基亚砜 、 lithium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， -78.0~70.0 ℃ 、101.33 kPa 条件下， 反应 43.47h， 生成 tert-butyl (5-(4-octylphenethyl)-2-phenyl-1,3-dioxan-5-yl)carbamate
  参考文献：
  名称：

  A convergent synthesis of the immunosuppressant FTY720 employing aqueous Wittig chemistry

  摘要：

  A short, convergent synthesis of the immunosuppressant FTY720 is described involving the use of 4-hydroxymethylbenzaldehyde as a pivotal intermediate. A double Wittig strategy was developed to connect this dual-functional aldehyde with an alkyl-tether and to a readily available TRIS-derivative leading to an efficient synthesis of the target molecule. (C) 2011 Elsevier Ltd. All rights reserved,

  DOI：

  10.1016/j.tetlet.2011.08.100
• 作为产物：
  描述：

  5-hydroxymethyl-5-nitro-2-phenyl-1,3-dioxane 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 86.0h， 生成 5-tert-butoxycarbonylamino-5-hydroxymethyl-2-phenyl-1,3-dioxane
  参考文献：
  名称：

  The total synthesis of antrimycin Dv

  摘要：

  抗结霉素Dv是一种代表性的抗结霉素和环拉霉素类结核抑制性庚肽抗生素，含有四氢吡嗪羧酸单元，已成功合成。

  DOI：

  10.1039/c39920001186

文献信息

• The total synthesis of antrimycin Dv
  作者：Ulrich Schmidt、Bernd Riedl

  DOI：10.1039/c39920001186

  日期：——

  Antrimycin Dv, a representative of the antrimycin and cirratiomycin classes of tuberculostatic heptapeptide anibiotics containing a tetrahydropyridazinecarboxylic acid unit, has been synthesized.

  抗结霉素Dv是一种代表性的抗结霉素和环拉霉素类结核抑制性庚肽抗生素，含有四氢吡嗪羧酸单元，已成功合成。
• Tandem oxidative radical fragmentation–rearrangement of 2-amino-1,3-benzylidene acetals: a short entry to densely functionalised fully differentiated oxazolidinones
  作者：James McNulty、Janice Calzavara

  DOI：10.1039/c3ra40218e

  日期：——

  The discovery of a novel tandem fragmentation–rearrangement process from N-Boc-protected benzylidene acetals is reported. The reaction proceeds via free-radical initiation and terminates through a 5-exo-tet ionic fragmentation process leading to biologically useful, densely functionalised oxazolidinones.

  报道了一种从N-Boc保护的苯亚甲基醛酸酯中发现的新型串联碎裂-重排过程。该反应通过自由基引发，并通过5-exo-tet离子碎裂过程终止，产生生物学上有用的高功能化氧杂环己酮。
• A Highly Regio- and Chemoselective Reductive Cleavage of Benzylidene Acetals with EtAlCl₂-Et₃SiH
  作者：Sundarababu Baskaran、Vijayakrishnan Balakumar、Appu Aravind

  DOI：10.1055/s-2004-817752

  日期：——

  A highly regio- and chemoselective reductive cleavage of benzylidene acetals derived from 1,2- and 1,3-diols was achieved under mild conditions using EtAlCl2-Et3SiH reagent system in good to excellent yields. Labile protecting groups such as N-Boc, N-Cbz and -OTBDMS are found to be stable under the reaction conditions.

  在温和的条件下，使用 EtAlCl2-Et3SiH 试剂体系实现了对源自 1,2- 和 1,3- 二醇的亚苄基乙缩醛的高区域和化学选择性还原裂解，并获得了良好甚至优异的产率。在反应条件下，N-叔丁氧羰基、N-苄氧羰基和 -OTBDMS 等易变保护基团都很稳定。
• Synthesis of fluorinated analogues of the immunosuppressive drug FTY720
  作者：Rebecca Y.Y. Ko、John C.K. Chu、Pauline Chiu

  DOI：10.1016/j.tet.2011.02.028

  日期：2011.4

  Four fluorinated derivatives of the immunosuppressive drug FTY720 were synthesized by a convergent strategy, using the Sonogashira coupling as the key reaction to assemble the two major fragments. (C) 2011 Elsevier Ltd. All rights reserved.
• The Total Synthesis of Antrimycin D_v; III:¹Construction of the Protected Hexapeptide and Deprotection
  作者：Ulrich Schmidt、Bernd Riedl

  DOI：10.1055/s-1993-25948

  日期：——

  In the preceding communication we described the synthesis of tetrahydropyridazine-3-carboxylic acids and their incorporation into peptides. We have also prepared the tripeptide 2 which is contained in the antibiotic antrimycin Dv 15. We now report on the preparation of the building blocks 1 and 4 and their coupling with 2 to give the protected antrimycin Dv 14. The deprotection of this heptapeptide constitutes the total synthesis of antrimycin Dv.

  在前文中，我们描述了四氢吡嗪-3-羧酸的合成及其并入多肽的过程。我们还制备了三肽2，该三肽包含在抗生素安曲霉素Dv 15中。现在我们报告了构建单元1和4的制备，以及它们与2的耦合，从而得到保护型的安曲霉素Dv 14。这个庚肽的去保护步骤构成了安曲霉素Dv的完全合成。