(2R,3R)-1,2-O-cyclohexylidene-4-octadecyne-1,2,3-triol | 471907-64-9

• 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)-1,2-O-cyclohexylidene-4-octadecyne-1,2,3-triol
• 英文别名: (1R)-1-[(3R)-1,4-dioxaspiro[4.5]decan-3-yl]hexadec-2-yn-1-ol
• CAS: 471907-64-9
• 化学式: C₂₄H₄₂O₃
• 分子量: 378.596
• InChiKey: KJMMQUYOHCBKQR-DHIUTWEWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  27
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  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 、 吡啶 、 二氯甲烷 为溶剂， 反应 10.0h， 生成 (2S,3R,4E)-3-benzoyloxy-1-thexyldimethylsilyloxy-octadec-4-ene-2-ol
  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
• 作为产物：
  描述：

  1-十五炔 、 (R)-1,4-二氧杂螺[4,5]癸烷-2-甲醛 在 乙基溴化镁 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 1.0h， 生成 (2R,3R)-1,2-O-cyclohexylidene-4-octadecyne-1,2,3-triol 、 (1S)-1-[(3R)-1,4-dioxaspiro[4.5]decan-3-yl]hexadec-2-yn-1-ol
  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 a Fluorescent Sulfatide for the Study of CD1 Antigen Binding Properties
  作者：Laura Franchini、Federica Compostella、Alena Donda、Lucia Mori、Diego Colombo、Gennaro De Libero、Pamela Matto、Fiamma Ronchetti、Luigi Panza

  DOI：10.1002/ejoc.200400398

  日期：2004.12

  A fluorescent derivative of sulfatide, labeled with a dansyl probe at position 6 of galactose, was prepared through a glycosylation reaction between a 6-O-functionalized galactose donor and 3-O-benzoyl-azidosphingosine. The sphingoid acceptor was obtained in high yield through exploitation of a highly stereoselective nucleophilic addition of pentadecyne to 2,3-O-cyclohexylidene-D-glyceraldehyde. The

  通过 6-O-功能化的半乳糖供体和 3-O-苯甲酰基-叠氮基鞘氨醇之间的糖基化反应，在半乳糖的 6 位用丹酰探针标记了硫苷脂的荧光衍生物。通过利用十五炔与 2,3-O-亚环己基-D-甘油醛的高度立体选择性亲核加成，以高产率获得了鞘氨醇受体。荧光硫苷脂与可溶性重组人 CD1a 结合，是研究 CD1 抗原结合特性的宝贵工具。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)
• 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.