(2R,3S,4R)-2,3,4-tribenzyloxy-hex-5-ene-1-al diethyl dithioacetal | 343934-65-6

• 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: (2R,3S,4R)-2,3,4-tribenzyloxy-hex-5-ene-1-al diethyl dithioacetal
• 英文别名: [(2R,3S,4R)-1,1-bis(ethylsulfanyl)-3,4-bis(phenylmethoxy)hex-5-en-2-yl]oxymethylbenzene
• CAS: 343934-65-6
• 化学式: C₃₁H₃₈O₃S₂
• 分子量: 522.773
• InChiKey: YZYMIQKSJUPOCU-DYIKCSJPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  36
• 可旋转键数：
  17
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  78.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,3S,4R)-2,3,4-tribenzyloxy-hex-5-ene-1-al diethyl dithioacetal 在 N-溴代丁二酰亚胺(NBS) 、 无水碳酸镉 作用下， 以 水 、 丙酮 为溶剂， 反应 0.67h， 以77%的产率得到2,3,4-tri-O-benzyl-5,6-dideoxy-D-xylo-hex-5-enose
  参考文献：
  名称：

  Cycloaddition reactions of carbohydrate derivatives. Part 8: Intramolecular cycloaddition of nitrilimines derived from sugars

  摘要：

  Nitrilimines containing a carbon-carbon double bond were prepared in several steps from 3,3,4-tri-O-benzyl-D-xylose, D-ribose and L-arabinose derivatives and their intramolecular 1,3-dipolar cycloaddition reactions were studied. The results were examined with molecular modelling and compared with the literature data for similar cycloadditions. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00050-7
• 作为产物：
  描述：

  2,3,4-tri-O-benzyl-D-xylose diethyl dithioacetal 在 正丁基锂 、 pyridinium chlorochromate 作用下， 以 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 3.0h， 生成 (2R,3S,4R)-2,3,4-tribenzyloxy-hex-5-ene-1-al diethyl dithioacetal
  参考文献：
  名称：

  Cycloaddition reactions of carbohydrate derivatives. Part 8: Intramolecular cycloaddition of nitrilimines derived from sugars

  摘要：

  Nitrilimines containing a carbon-carbon double bond were prepared in several steps from 3,3,4-tri-O-benzyl-D-xylose, D-ribose and L-arabinose derivatives and their intramolecular 1,3-dipolar cycloaddition reactions were studied. The results were examined with molecular modelling and compared with the literature data for similar cycloadditions. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00050-7

文献信息

• Stereoselective Synthesis and Absolute Configuration of the C1′−C25′ Fragment of Symbiodinolide
  作者：Hiroyoshi Takamura、Takeshi Murata、Takahiro Asai、Isao Kadota、Daisuke Uemura

  DOI：10.1021/jo901162v

  日期：2009.9.4

  Stereoselective synthesis of the C1′−C25′ fragment of symbiodinolide, which was obtained as a degraded product from symbiodinolide by alkaline hydrolysis, has been accomplished. The synthetic route features Kotsuki coupling and Julia−Kocienski olefination in the introduction of the side chains. This enantio- and stereoselective synthesis has established the absolute configuration of the C1′−C25′ fragment.

  已经完成了共生双杀菌素的C1'-C25'片段的立体选择性合成，该共生双杀菌素是通过碱水解从共生双杀菌素的降解产物中获得的。在侧链的引入中，合成路线的特征是Kotsuki偶联和Julia-Kocienski烯烃化。该对映和立体选择性合成已经建立了C1'-C25'片段的绝对构型。