(2S)-2-(N-tert-butoxycarbonyl)amino-1-hydroxyoctadecan-3-one | 437609-37-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S)-2-(N-tert-butoxycarbonyl)amino-1-hydroxyoctadecan-3-one
• 英文别名: (2S)-2-(tert-butoxycarbonylamino)-1-hydroxyoctadecan-3-one；(2S)-2-(t-butoxycarbonylamino)-1-hydroxyoctadecan-3-one；tert-butyl (S)-(1-hydroxy-3-oxooctadecan-2-yl)carbamate；tert-butyl N-[(2S)-1-hydroxy-3-oxooctadecan-2-yl]carbamate
• CAS: 437609-37-5
• 化学式: C₂₃H₄₅NO₄
• 分子量: 399.615
• InChiKey: LPOMBISEMRIEHC-FQEVSTJZSA-N

物化性质

• 熔点：
  48-50 °C
• 沸点：
  520.0±40.0 °C(Predicted)
• 密度：
  0.961±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  28
• 可旋转键数：
  19
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S)-2-(N-tert-butoxycarbonyl)amino-1-hydroxyoctadecan-3-one 在 lithium tri-t-butoxyaluminum hydride 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以98%的产率得到N-叔-丁基氧羰基-D-赤式-二氢-D-鞘氨醇
  参考文献：
  名称：

  Straightforward Synthesis of Sphinganines via a Serine-derived Weinreb Amide

  摘要：

  Sphinganines can be synthesized in just three steps from easily prepared serine-derived Weinreb amide 4. Pre-deprotonation of the acidic (N-H and O-H) protons of 4 allows for its efficient conversion to amino ketones 5. Such ketones can be selectively reduced to either erythro- or threo-sphinganines. Partially protected sphinganines 11 are also readily accessible in five steps from 4. Thus, Weinreb amide 4 represents one of the most versatile templates described to date for sphinganine synthesis.

  DOI：

  10.1021/jo030355b
• 作为产物：
  描述：

  BOC-L-丝氨酸 在 N-甲基吗啉 、 仲丁基锂 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 4.08h， 生成 (2S)-2-(N-tert-butoxycarbonyl)amino-1-hydroxyoctadecan-3-one
  参考文献：
  名称：

  Simplifungin and Valsafungins, Antifungal Antibiotics of Fungal Origin

  摘要：

  The targets of antifungal antibiotics in clinical use are more limited than those of antibacterial antibiotics. Therefore, new antifungal antibiotics with different mechanisms of action are desired. In the course of our screening for antifungal antibiotics of microbial origins, new antifungal antibiotics, simplifungin (1) and valsafungins A (2) and B (3), were isolated from cultures of the fungal strains Simplicillium minatense FKI-4981 and Valsaceae sp. FKH-53, respectively. The structures of 1 to 3 including their absolute stereochemistries were elucidated using various spectral analyses including NMR and collision-induced dissociation (CID)-MS/MS as well as chemical approaches including modifications to the Mosher's method. They were structurally related to myriocin. They inhibited the growth of yeast-like and zygomycetous fungi with MICs ranging between 0.125 and 8.0 mu g/mL. An examination of their mechanisms of action by the newly established assay using LC-MS revealed that 1 and 2 inhibited serine palmitoyltransferase activity, which is involved in sphingolipid biosynthesis, with IC50 values of 224 and 24 nM, respectively.

  DOI：

  10.1021/acs.joc.6b00952

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.
• Synthesis of <scp>d</scp>-<i>e</i><i>rythro</i>-Dihydrosphingosine and <scp>d</scp>-<i>x</i><i>ylo</i>-Phytosphingosine from a Serine-Derived 1,5-Dioxaspiro[3.2]hexane Template
  作者：Albert J. Ndakala、Mehrnoosh Hashemzadeh、Regina C. So、Amy R. Howell

  DOI：10.1021/ol0200448

  日期：2002.5.1

  [GRAPHICS]A serine-derived 1,5-dioxaspiro[3,2]hexane template is shown to be a useful precursor for both aminodiol and aminotriol sphingoid bases by its conversion to D-erythro-dihydrosphingosine and D-xylo-phytoshingosine.
• Straightforward Synthesis of Sphinganines via a Serine-derived Weinreb Amide
  作者：Regina C. So、Rachel Ndonye、Douglas P. Izmirian、Stewart K. Richardson、Robyn L. Guerrera、Amy R. Howell

  DOI：10.1021/jo030355b

  日期：2004.4.1

  Sphinganines can be synthesized in just three steps from easily prepared serine-derived Weinreb amide 4. Pre-deprotonation of the acidic (N-H and O-H) protons of 4 allows for its efficient conversion to amino ketones 5. Such ketones can be selectively reduced to either erythro- or threo-sphinganines. Partially protected sphinganines 11 are also readily accessible in five steps from 4. Thus, Weinreb amide 4 represents one of the most versatile templates described to date for sphinganine synthesis.
• Simplifungin and Valsafungins, Antifungal Antibiotics of Fungal Origin
  作者：Hiroyuki Ishijima、Ryuji Uchida、Masaki Ohtawa、Ariko Kondo、Kenichiro Nagai、Keisuke Shima、Kenichi Nonaka、Rokuro Masuma、Susumu Iwamoto、Hideyuki Onodera、Tohru Nagamitsu、Hiroshi Tomoda

  DOI：10.1021/acs.joc.6b00952

  日期：2016.9.2

  The targets of antifungal antibiotics in clinical use are more limited than those of antibacterial antibiotics. Therefore, new antifungal antibiotics with different mechanisms of action are desired. In the course of our screening for antifungal antibiotics of microbial origins, new antifungal antibiotics, simplifungin (1) and valsafungins A (2) and B (3), were isolated from cultures of the fungal strains Simplicillium minatense FKI-4981 and Valsaceae sp. FKH-53, respectively. The structures of 1 to 3 including their absolute stereochemistries were elucidated using various spectral analyses including NMR and collision-induced dissociation (CID)-MS/MS as well as chemical approaches including modifications to the Mosher's method. They were structurally related to myriocin. They inhibited the growth of yeast-like and zygomycetous fungi with MICs ranging between 0.125 and 8.0 mu g/mL. An examination of their mechanisms of action by the newly established assay using LC-MS revealed that 1 and 2 inhibited serine palmitoyltransferase activity, which is involved in sphingolipid biosynthesis, with IC50 values of 224 and 24 nM, respectively.