(D)-xylo-octadecane-1,2,3,4-tetrol | 105368-62-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (D)-xylo-octadecane-1,2,3,4-tetrol
• 英文别名: (2S,3S,4R)-octadecane-1,2,3,4-tetrol
• CAS: 105368-62-5
• 化学式: C₁₈H₃₈O₄
• 分子量: 318.497
• InChiKey: VTIMCYVWFFHKIG-SQNIBIBYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  22
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  80.9
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 (D)-xylo-octadecane-1,2,3,4-tetrol 在 三乙胺 、 碳酸氢钠 作用下， 以 N,N-二甲基甲酰胺 、 水 、 乙酸乙酯 为溶剂， 反应 12.0h， 以70%的产率得到1,2(S),3(S),4(R)-tetra-O-acetyl-octadecanetetrol
  参考文献：
  名称：

  从d-葡萄糖构型的通用构件轻松合成d-和l-xylo-1,2,3,4-烷烃四元醇

  摘要：

  衍生自D-（+）-葡糖酸内酯的D-葡萄糖构筑的构建基块已成为合成对映体纯D-和L-二甲苯基构筑的1,2,3,4-烷四醇的通用手性模板。从一个共同的出发点，就可以合成具有医学重要性的古吉特罗及其对映异构体。Wittig和Grignard反应是掺入亲脂性链的关键步骤。

  DOI：

  10.1016/j.carres.2012.06.005
• 作为产物：
  描述：

  octadecane-1,2S,3S,4R-tetrol 1-O-α-L-rhamnopyranoside 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以8 mg的产率得到(D)-xylo-octadecane-1,2,3,4-tetrol
  参考文献：
  名称：

  Secondary metabolites from Commiphora opobalsamum and their antiproliferative effect on human prostate cancer cells

  摘要：

  A cycloartane-type triterpenoid (1), an aliphatic alcohol glycoside (2), an eudesmane-type sesquiterpenoid (3), and a guaiane-type sesquiterpenoid (4) were isolated from the resinous exudates of Commiphora opobalsamum along with six known sesquiterpenoids (5-10). Their structures were established by extensive analysis of their 1D and 2D NMR spectroscopic data and chemical methods. The isolated compounds 1-3 and 5-9 were tested against human prostate cancer cell PC 3 and LNCaP. Among them, I and 2 showed moderate anti-proliferative effects on human prostate cancer cell lines with IC50 values ranging from 5.7 to 23.6 mu M; they were also able to inhibit the expression of androgen receptor (AR) in LNCaP cells. The six sesquiterpenoids were inactive in the bioassays. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2007.01.013

文献信息

• Synthesis and properties of some stereoisomeric long-chain 1,2,3,4-tetrols
  作者：Anders Kjer、Dana Kjer、Troels Skrydstrup

  DOI：10.1016/s0040-4020(01)87363-4

  日期：1986.1

  Syntheses of 1, 2, 3, 4, 1, 2, 3, 4, 1, 2, 3, 4, and 1, 2, 3, 4- icosanetetrol, as well as of 1, 2, 3, 4-octadecanetetrol, are described, all based upon Wittig reactions of 1,2,3-protected pentodialdo-1,4-furanoses, serving as “chiral templates”, with pentadecyl (or tridecyl) triphenyIphosphorane, followed by catalytic hydrogenation, hydrolysis, and reduction. The tetrols, all forming liquid crystals

  的1的合成，2 ，3 ，4 ，1，2 ，3 ，4 ，1，2 ，3 ，4 ，和1，2 ，3 ，4 - icosanetetrol，以及1,2 ，3 ，4 -octadecanetetrol描述了所有这些，都是基于1,2,3-被保护的戊二醛-1,4-呋喃糖酶（用作“手性模板”）与十五烷基（或十三烷基）三苯并膦膦的维蒂希反应，然后进行催化氢化，水解和还原反应。这些四醇在加热时全部形成液晶，其光谱学特征和特征在于-四乙酸盐。后者可用于所有非对映体四元醇的GLC分离和表征。从旋转的迹象和与合成的四乙酸酯的GLC比较可以得出，几年前报道的1,2,3,4-十八烯醇和1,2,3,4-二十碳烯醇是1,2,3,4-十八碳甾醇的同源序列的主要成员。从胶系树脂衍生的四元醇，具有2个，3个，4 - configuratlon（ 'd-低聚木糖'）。
• Stereoselective syntheses of γ-alkyl (aryl)-α,β-dihydroxy-γ-butyrolactones and naturally occurring lipid guggultetrol
  作者：Kavirayani R. Prasad、Appayee Chandrakumar

  DOI：10.1016/j.tet.2006.12.037

  日期：2007.2

  gamma-Oxo-butyramides derived from tartaric acid serve as excellent precursors for the synthesis of gamma-alkyl (aryl)-alpha,beta-dihydroxy-gamma-butyrolactones and for the synthesis of tetrols containing three contiguous stereogenic centres. The methodology presented here is general for the synthesis of gamma-alkyl (aryl)-alpha,beta-dihydroxy-gamma-butyrolactones. Utility of the chiral building block was demonstrated by the synthesis of naturally occurring lipid guggultetrol. (c) 2006 Elsevier Ltd. All rights reserved.
• A short enantioselective synthesis of guggultetrol, a naturally occurring lipid
  作者：Shyla George、Gurunath Suryavanshi、Arumugam Sudalai

  DOI：10.1016/j.tetasy.2010.02.019

  日期：2010.3

  An enantioselective synthesis of the naturally occurring lipid, guggultetrol, is described with an overall yield of 24% starting from commercially available 1-pentadecanol in ten linear steps. The key chiral-inducing steps include a Sharpless asymmetric epoxidation of allylic alcohol and a dihydroxylation of an alpha,beta-unsaturated ester. (C) 2010 Elsevier Ltd. All rights reserved.
• Convenient synthesis of d- and l-xylo-1,2,3,4-alkane tetrols from a d-gluco-configured common building block
  作者：Santosh Ramdas Borkar、Beedimane Narayana Manjunath、Sivaraman Balasubramaniam、Indrapal Singh Aidhen

  DOI：10.1016/j.carres.2012.06.005

  日期：2012.9

  D-gluco-configured building block derived from D-(+)-gluconolactone has served as a common chiral template for the synthesis of enantiopure D- and L-xylo-configured 1,2,3,4-alkane tetrols. This has enabled synthesis of medicinally important guggultetrols and their enantiomers from a common starting point. Wittig and Grignard reactions are the key steps used for the incorporation of lipophilic chain

  衍生自D-（+）-葡糖酸内酯的D-葡萄糖构筑的构建基块已成为合成对映体纯D-和L-二甲苯基构筑的1,2,3,4-烷四醇的通用手性模板。从一个共同的出发点，就可以合成具有医学重要性的古吉特罗及其对映异构体。Wittig和Grignard反应是掺入亲脂性链的关键步骤。
• Secondary metabolites from Commiphora opobalsamum and their antiproliferative effect on human prostate cancer cells
  作者：Tao Shen、Wenzhu Wan、Huiqing Yuan、Feng Kong、Huaifang Guo、Peihong Fan、Hongxiang Lou

  DOI：10.1016/j.phytochem.2007.01.013

  日期：2007.5

  A cycloartane-type triterpenoid (1), an aliphatic alcohol glycoside (2), an eudesmane-type sesquiterpenoid (3), and a guaiane-type sesquiterpenoid (4) were isolated from the resinous exudates of Commiphora opobalsamum along with six known sesquiterpenoids (5-10). Their structures were established by extensive analysis of their 1D and 2D NMR spectroscopic data and chemical methods. The isolated compounds 1-3 and 5-9 were tested against human prostate cancer cell PC 3 and LNCaP. Among them, I and 2 showed moderate anti-proliferative effects on human prostate cancer cell lines with IC50 values ranging from 5.7 to 23.6 mu M; they were also able to inhibit the expression of androgen receptor (AR) in LNCaP cells. The six sesquiterpenoids were inactive in the bioassays. (c) 2007 Elsevier Ltd. All rights reserved.