(2R,3R,4E)-3-benzoyloxyoctadec-4-ene-1,2-diol | 202464-96-8

• 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: (2R,3R,4E)-3-benzoyloxyoctadec-4-ene-1,2-diol
• 英文别名: [(E,2R,3R)-1,2-dihydroxyoctadec-4-en-3-yl] benzoate
• CAS: 202464-96-8
• 化学式: C₂₅H₄₀O₄
• 分子量: 404.59
• InChiKey: WNVDHUBGRVOEQA-QIOSQNANSA-N

物化性质

• 沸点：
  540.9±50.0 °C(Predicted)
• 密度：
  1.018±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  29
• 可旋转键数：
  18
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,3R,4E)-3-benzoyloxyoctadec-4-ene-1,2-diol 在 吡啶 、 sodium azide 、 sodium methylate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 53.0h， 生成 (2S,3R,4E)-2-叠氮-4-十八碳烯-1,3-二醇
  参考文献：
  名称：

  An Efficient Stereoselective Synthesis of Sphingosine

  摘要：

  本文介绍了一种立体可控的 d-(+)-赤藓-鞘氨醇 (1) 合成方法，该方法以 d-木糖为手性池材料，采用 2,3 : 4,5-di-O-isopropylidene-dxylose 的甲苯腙的加成-分裂反应作为链延伸的关键步骤，同时进行反式选择性 C=C 键形成。

  DOI：

  10.1055/s-1998-4482
• 作为产物：
  描述：

  (2R,3R)-1,2-O-cyclohexylidene-4-octadecyne-1,2,3-triol 在 吡啶 、 lithium aluminium tetrahydride 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 10.0h， 生成 (2R,3R,4E)-3-benzoyloxyoctadec-4-ene-1,2-diol
  参考文献：
  名称：

  Chemoenzymatic stereoconvergent synthesis of 3-O-benzoyl azidosphingosine

  摘要：

  The synthesis of 3-O-benzoyl azidosphingosine 1 through a stereoconvergent approach is described. Nucleophilic addition of the Grignard reagent of 1-pentadecyne to cyclohexylidene-D-glyceraldehyde results in a mixture of diastereoisomeric propargylic alcohols. Subsequent enzymatic separation of these diastereoisomers, mediated by lipase from Candida antarctica, Mitsunobu inversion on the wrong diastereoisomer and extremely efficient introduction of azide using a chloromesylate leaving group affords the title compound in 30% overall yield. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00201-x

文献信息

• Synthesis of an orthogonally protected d-(+)-erythro-sphingosine
  作者：Joseph M Gargano、Watson J Lees

  DOI：10.1016/s0040-4039(01)01152-2

  日期：2001.8

  The synthesis presented provides rapid access to an orthogonally protected d-(+)-erythro-sphingosine: 1-methoxymethyl, 2-azido, 3-benzoyl. After selective deprotection the resulting sphingosine derivative is suitable for coupling to a wide variety of saccharides or other molecules at either the 1- or 3-position.

  提出的合成提供了快速获得正交保护的d-（+）-赤型-鞘氨醇的途径：1-甲氧基甲基，2-叠氮基，3-苯甲酰基。选择性脱保护后，所得的鞘氨醇衍生物适合于在1-或3-位偶联至多种糖或其他分子。
• A short and practical route to 3-O-benzoyl azidosphingosine
  作者：Jörgen Ohlsson、Göran Magnusson

  DOI：10.1016/s0008-6215(00)00323-2

  日期：2001.3

  A short and practical route to 3-O-benzoyl azidosphingosine from D-xylose is described. The synthesis avoids the use of expensive and hazardous chemicals (i.e. mercury salts), and it is reproducible up to at least a 20 g scale. Furthermore, the synthesis proceeds to 3-O-benzoyl azidosphingosine with a minimum of protection group manipulation, by exploiting a regioselective protection of the primary

  描述了从D-木糖制备3-O-苯甲酰基叠氮鞘氨醇的短而实用的途径。合成过程避免使用昂贵和危险的化学药品（例如汞盐），并且可重现至少20 g的规模。此外，通过利用伯基二甲基甲硅烷基氯对伯HO-1进行区域选择性保护，合成以最少的保护基团操作进行到3-O-苯甲酰基叠氮基鞘氨醇。
• Synthesis of α-l-rhamnosyl ceramide and evaluation of its binding with anti-rhamnose antibodies
  作者：David E. Long、Partha Karmakar、Katherine A. Wall、Steven J. Sucheck

  DOI：10.1016/j.bmc.2014.08.002

  日期：2014.10

  An α-L-rhamnosyl ceramide (1, α-L-RhaCer) has been prepared that was recognized by anti-L-rhamnose (anti-Rha) antibodies. During these studies we explored the use of an α-L-rhamnosyl thioglycoside and a trichloroacetimidate as a glycosyl donors. Subsequently, the acceptors desired for glycosylation, 3-O-benzoylazidosphingosine or 3-O-alloxycarbonylsphingosine, were prepared from D-xylose. The thioglycoside donor, 2,3,4-tri-O-acetyl-1-(4-tolyl)thio-α-L-rhamnopyranoside, and the trichloroacetimidate donor, 2,3,4-tri-O-acetyl-1-(2,2,2-trichloroethanimidate)-α-L-rhamnopyranoside, were synthesized in 50% and 78% yield overall, respectively. The synthesis of the glycosylation acceptor employed an addition-fragmentation olefination that was successfully carried out in 53% yield. With the successful synthesis of key intermediates, α-L-RhaCer (1) was prepared without any insurmountable obstacles. Anti-Rha antibodies were prepared in BALB/c mice by immunizing them with rhamnose-ovalbumin (Rha-Ova) with Sigma Adjuvant System (SAS) and the anti-L-Rha antibodies were isolated from the blood sera. Liposomes and EL4 tumor cells were used as model systems to demonstrate the ability of 1 to insert into a lipid bilayer. The interaction of the liposomes or the EL4 cells with α-L-RhaCer (1) and anti-Rha antibodies were investigated by fluorescence microscopy and flow cytometry, respectively, to confirm the ability of glycolipid 1 to be displayed on the tumor cell surface as well as the ability to be recognized by anti-Rha antibodies.
• Chemoenzymatic stereoconvergent synthesis of 3-O-benzoyl azidosphingosine
  作者：Federica Compostella、Laura Franchini、Giovanni Battista Giovenzana、Luigi Panza、Davide Prosperi、Fiamma Ronchetti

  DOI：10.1016/s0957-4166(02)00201-x

  日期：2002.5

  The synthesis of 3-O-benzoyl azidosphingosine 1 through a stereoconvergent approach is described. Nucleophilic addition of the Grignard reagent of 1-pentadecyne to cyclohexylidene-D-glyceraldehyde results in a mixture of diastereoisomeric propargylic alcohols. Subsequent enzymatic separation of these diastereoisomers, mediated by lipase from Candida antarctica, Mitsunobu inversion on the wrong diastereoisomer and extremely efficient introduction of azide using a chloromesylate leaving group affords the title compound in 30% overall yield. (C) 2002 Elsevier Science Ltd. All rights reserved.
• An Efficient Stereoselective Synthesis of Sphingosine
  作者：Pradeep Kumar、Richard R. Schmidt

  DOI：10.1055/s-1998-4482

  日期：1998.1

  A stereocontrolled synthesis of d-(+)-erythro-sphingosine (1), starting from d-xylose as chiral pool material and employing the addition-fragmentation reaction of tosyl hydrazone of 2,3 : 4,5-di-O-isopropylidene-d-xylose as key step for the chain extension with concomitant trans-selective C=C bond formation, is described.

  本文介绍了一种立体可控的 d-(+)-赤藓-鞘氨醇 (1) 合成方法，该方法以 d-木糖为手性池材料，采用 2,3 : 4,5-di-O-isopropylidene-dxylose 的甲苯腙的加成-分裂反应作为链延伸的关键步骤，同时进行反式选择性 C=C 键形成。