(Z)-(R)-N-Boc-2,2-dimethyl-4-(1-heptenyl)oxazolidine | 133625-91-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (Z)-(R)-N-Boc-2,2-dimethyl-4-(1-heptenyl)oxazolidine
• 英文别名: (4R,1'Z)-3-(tert-butoxycarbonyl)-2,2-dimethyl-1-(1'-heptenyl)oxazolidine；tert-butyl (4R)-4-[(Z)-hept-1-enyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• CAS: 133625-91-9
• 化学式: C₁₇H₃₁NO₃
• 分子量: 297.438
• InChiKey: JYVXWCNJZSEFSK-XMXAVACDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-(R)-N-Boc-2,2-dimethyl-4-(1-heptenyl)oxazolidine 在 4-二甲氨基吡啶 、 sodium chlorite 、 四氧化锇 、 sodium dihydrogenphosphate dihydrate 、 2-甲基-2-丁烯 、 sodium hydride 、 溶剂黄146 、 N-甲基吗啉氧化物 、 N,N'-二异丙基碳二亚胺 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 水 、 乙酸乙酯 、 叔丁醇 为溶剂， 生成 (2S,3R,4S,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-(bromodifluoromethyl)tetrahydro-2H-pyran-3-yl (2R,3S,4R)-3,4-bis(benzyloxy)-2-((tertbutoxycarbonyl)amino)nonanoate
  参考文献：
  名称：

  氟化α-C-半乳糖基神经酰胺类似物的合成和免疫学评价

  摘要：

  报道了在1'-位具有额外羟基的二氟化α-C-半乳糖基神经酰胺类似物的合成。这些化合物是根据作者先前在较简单的底物上报道的空前和不寻常的方法制备的。不幸的是，所有四个具有不同脂链长度的化合物均未能激活iNKT细胞。到底是由于端基氧/ CF 2的转位还是由于额外的OH基的存在，这一问题仍未得到解答。

  DOI：

  10.1016/j.jfluchem.2015.02.014
• 作为产物：
  描述：

  己基三苯基碘化膦 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.0h， 生成 (Z)-(R)-N-Boc-2,2-dimethyl-4-(1-heptenyl)oxazolidine
  参考文献：
  名称：

  Synthesis of chiral vinylglycines

  摘要：

  (R)- or (S)-benzyl 4-formyl-2,2-dimethyl-3-oxazolidinecarboxylate (7a) and (R)- or (S)-1,1-dimethylethyl 4-formyl-2,2-dimethyl-3-oxazolidinecarboxylate (7b), readily available from serine, react with Wittig reagents to give alkenes 8. Selective deprotection followed by oxidation of the resulting unsaturated amino alcohols 9 provides vinylglycines 5 of defined configuration (> 95% ee) and double-bond geometry. D-Vinylglycines are obtained from L-serine, and conversely, D-serine gives beta,gamma-unsaturated amino acids with the L configuration. The double-bond geometry is controlled by the nature of the phosphorous ylide employed. The scope and limitations of this new methodology for the preparation of chiral vinylglycines is examined.

  DOI：

  10.1021/jo00013a023

文献信息

• Synthesis and Evaluation of Sphinganine Analogues of KRN7000 and OCH
  作者：Rachel M. Ndonye、Douglas P. Izmirian、Matthew F. Dunn、Karl O. A. Yu、Steven A. Porcelli、Archana Khurana、Mitchell Kronenberg、Stewart K. Richardson、Amy R. Howell

  DOI：10.1021/jo051147h

  日期：2005.12.1

  The phytosphingosine-containing alpha-galactosylceramides (alpha-GalCers), KRN7000 and OCH, have been shown to activate NKT cells via interaction with CD1d, a member of the CD1 family of antigen presenting proteins. Evidence from KRN7000 stimulation of NKT cells suggests that alpha-GalCers may have applications in the treatment or prevention of a range of viral, bacterial, and autoimmune conditions. Moreover, OCH, a truncated analogue of KRN7000, appears to induce a T(H)2 bias, which could have implications for the treatment of autoimmune and inflammatory conditions. We have prepared the direct sphinganine-containing analogues of KRN7000 and OCH, 1 and 2, and found them to be comparable in activity to the parent compounds in inducing the release of IL-2, IL-4, and IFN gamma. In addition, compound 2 leads to a cytokine bias similar to that seen with OCH. This is significant because sphinganines are more easily accessed than phytosphingosines, which should facilitate SAR studies.
• Effects of Lipid Chain Lengths in α-Galactosylceramides on Cytokine Release by Natural Killer T Cells
  作者：Randal D. Goff、Ying Gao、Jochen Mattner、Dapeng Zhou、Ning Yin、Carlos Cantu、Luc Teyton、Albert Bendelac、Paul B. Savage

  DOI：10.1021/ja045385q

  日期：2004.10.1

  Glycolipid presentation by CD1 proteins has emerged as an important aspect of antigen recognition, and presentation of alpha-glycosylceramides by CD1d to natural killer T cells has become a central focus in understanding how glycolipid presentation can influence immune responses. An alpha-galactosylceramide containing relatively long lipid chains has been the subject of intense study because, when presented by CD1d to natural killer T cells, it stimulates the release of both proinflammatory and immunomodulatory cytokines. Using an efficient synthesis of alpha-galactosylceramides, we have prepared a series of glycolipids in which the lipid chain lengths have been incrementally varied. The responses of natural killer T cells to these glycolipids have been determined, and we have found that truncation of the phytosphingosine lipid chain increases the relative amounts of immunomodulatory cytokines released. In similar fashion, the length of the acyl chain in alpha-galactosylceramides influences cytokine release profiles.
• Synthesis of chiral vinylglycines
  作者：Pierre L. Beaulieu、Jean Simon Duceppe、Carolyne Johnson

  DOI：10.1021/jo00013a023

  日期：1991.6

  (R)- or (S)-benzyl 4-formyl-2,2-dimethyl-3-oxazolidinecarboxylate (7a) and (R)- or (S)-1,1-dimethylethyl 4-formyl-2,2-dimethyl-3-oxazolidinecarboxylate (7b), readily available from serine, react with Wittig reagents to give alkenes 8. Selective deprotection followed by oxidation of the resulting unsaturated amino alcohols 9 provides vinylglycines 5 of defined configuration (> 95% ee) and double-bond geometry. D-Vinylglycines are obtained from L-serine, and conversely, D-serine gives beta,gamma-unsaturated amino acids with the L configuration. The double-bond geometry is controlled by the nature of the phosphorous ylide employed. The scope and limitations of this new methodology for the preparation of chiral vinylglycines is examined.
• Synthesis and immunological evaluation of fluorinated α-C-galactosylceramide analogs
  作者：Sophie Colombel、Nathalie Van Hijfte、Thomas Poisson、Xavier Pannecoucke、Fanny Monneaux、Eric Leclerc

  DOI：10.1016/j.jfluchem.2015.02.014

  日期：2015.5

  A synthesis of difluorinated α-C-galactosylceramides analogs featuring an extra hydroxy group in 1′-position is reported. These compounds were prepared according to unprecedented and unusual methodologies that were previously reported by the authors on simpler substrates. Unfortunately, all four compounds, which feature different lipidic chain lengths, failed to activate iNKT cells. The question whether

  报道了在1'-位具有额外羟基的二氟化α-C-半乳糖基神经酰胺类似物的合成。这些化合物是根据作者先前在较简单的底物上报道的空前和不寻常的方法制备的。不幸的是，所有四个具有不同脂链长度的化合物均未能激活iNKT细胞。到底是由于端基氧/ CF 2的转位还是由于额外的OH基的存在，这一问题仍未得到解答。