(2S,3S,4S)-2-azido-3,4-dihydroxy-octadecyl 4-methylbenzenesulfonate | 948850-77-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S,3S,4S)-2-azido-3,4-dihydroxy-octadecyl 4-methylbenzenesulfonate
• 英文别名: [(2S,3S,4S)-2-azido-3,4-dihydroxyoctadecyl] 4-methylbenzenesulfonate
• CAS: 948850-77-9
• 化学式: C₂₅H₄₃N₃O₅S
• 分子量: 497.7
• InChiKey: YNKZJHTWPDHYEH-SDHOMARFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.5
• 重原子数：
  34
• 可旋转键数：
  20
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  107
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2S,3S,4S)-2-azido-3,4-dihydroxy-octadecyl 4-methylbenzenesulfonate 在 palladium on activated charcoal 氢气 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 jaspine B
  参考文献：
  名称：

  Stereoselective Synthesis of Cytotoxic Anhydrophytosphingosine Pachastrissamine [Jaspine B]

  摘要：

  [GRAPHICS]A practical stereoselective synthesis of cytotoxic anhydrophytosphingosine pachastrissamine (jaspine B) was achieved in 48% overall yield from D-(-)-tartaric acid. Key features of the sequence include the diastereoselective formation of a tetrol with three contiguous chiral centers, which was further elaborated to pachastrissamine. The synthetic route is operationally simple, diastereoselective and is amenable for the synthesis of a number of analogues of pachastrissamine.

  DOI：

  10.1021/jo0707838
• 作为产物：
  描述：

  2-azido-3,4-O-isopropylidene-L-lyxo-1,3,4-octadecanetriol 在 三氯化铁 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 生成 (2S,3S,4S)-2-azido-3,4-dihydroxy-octadecyl 4-methylbenzenesulfonate
  参考文献：
  名称：

  Stereoselective Synthesis of Cytotoxic Anhydrophytosphingosine Pachastrissamine [Jaspine B]

  摘要：

  [GRAPHICS]A practical stereoselective synthesis of cytotoxic anhydrophytosphingosine pachastrissamine (jaspine B) was achieved in 48% overall yield from D-(-)-tartaric acid. Key features of the sequence include the diastereoselective formation of a tetrol with three contiguous chiral centers, which was further elaborated to pachastrissamine. The synthetic route is operationally simple, diastereoselective and is amenable for the synthesis of a number of analogues of pachastrissamine.

  DOI：

  10.1021/jo0707838

文献信息

• Nitrolaldol reaction of (R)-2,3-cyclohexylideneglyceraldehyde: a simple and stereoselective synthesis of the cytotoxic Pachastrissamine (Jaspine B)
  作者：Prasad Vichare、Angshuman Chattopadhyay

  DOI：10.1016/j.tetasy.2010.06.024

  日期：2010.8

  (R)-2,3-Cyclohexylideneglyceraldehyde 1 has been found to be a good substrate for nitroaldol reaction both in anhydrous and aqueous conditions. In both cases, the reaction took place with good substrate-controlled anti-selectivity. The major nitroaldol product 2b has been exploited to develop a simple and stereoselective synthesis of jaspine B X. Also, beginning with nitroaldol reaction of 1, this route presents a simple approach for the stereoselective preparation of (anti-anti-5,7)- and (syn-syn-9, 11, 12)-1,2,3,4-alkanetetrols, each possessing three contiguous oxygenated stereocenters. (C) 2010 Elsevier Ltd. All rights reserved.
• A novel stereoselective synthesis of pachastrissamine (jaspine B) starting from 1-pentadecanol
  作者：K. Venkatesan、K.V. Srinivasan

  DOI：10.1016/j.tetasy.2007.12.001

  日期：2008.2

  A novel stereoselective synthesis of pachastrissamine (jaspine B), starting from commercially available 1-pentadecanol is described. Sharpless asymmetric dihydroxylation and a chelation controlled vinyl Grignard reaction are the key steps in this synthetic strategy. (C) 2007 Elsevier Ltd. All rights reserved.
• Stereoselective Synthesis of Cytotoxic Anhydrophytosphingosine Pachastrissamine [Jaspine B]
  作者：Kavirayani R. Prasad、Appayee Chandrakumar

  DOI：10.1021/jo0707838

  日期：2007.8.1

  [GRAPHICS]A practical stereoselective synthesis of cytotoxic anhydrophytosphingosine pachastrissamine (jaspine B) was achieved in 48% overall yield from D-(-)-tartaric acid. Key features of the sequence include the diastereoselective formation of a tetrol with three contiguous chiral centers, which was further elaborated to pachastrissamine. The synthetic route is operationally simple, diastereoselective and is amenable for the synthesis of a number of analogues of pachastrissamine.