2-deoxy-3-O-(tert-butyldiphenylsilyl)-4,5-O-isopropylidene-D-erythro-pentose diethyl dithioacetal | 93292-41-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-deoxy-3-O-(tert-butyldiphenylsilyl)-4,5-O-isopropylidene-D-erythro-pentose diethyl dithioacetal
• 英文别名: 3-O-(tert-butyldiphenylsilyl)-2-deoxy-4,5-O-isopropylidene-D-erythro-pentose diethyl dithioacetal；tert-butyl-[(1S)-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-3,3-bis(ethylsulfanyl)propoxy]-diphenylsilane
• CAS: 93292-41-2
• 化学式: C₂₈H₄₂O₃S₂Si
• 分子量: 518.857
• InChiKey: LGQONOBSPZJRKM-LOSJGSFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.31
• 重原子数：
  34
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 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：

  2-deoxy-3-O-(tert-butyldiphenylsilyl)-4,5-O-isopropylidene-D-erythro-pentose diethyl dithioacetal 在 lead(IV) acetate 、 N-氯代丁二酰亚胺 、 正丁基锂 、 sodium hydride 、 sodium carbonate 、 silver nitrate 、 三氟乙酸 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 水 、 乙腈 、 苯 为溶剂， 反应 17.0h， 生成 ethyl 5(S)-(benzoyloxy)-12(R)-<(tert-butyldiphenylsilyl)oxy>-6(Z),8(E),10(E),14(Z)-icosatetraenoate
  参考文献：
  名称：

  Simple efficient synthesis of LTB4 and 12-epi-LTB4

  摘要：

  DOI：

  10.1016/s0040-4039(00)87415-8
• 作为产物：
  描述：

  2,3:4,5-di-O-isopropylidene-D-arabinose diethyldithioacetal 在 lithium aluminium tetrahydride 、 potassium tert-butylate 、 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 27.0h， 生成 2-deoxy-3-O-(tert-butyldiphenylsilyl)-4,5-O-isopropylidene-D-erythro-pentose diethyl dithioacetal
  参考文献：
  名称：

  Cyclopropane-Containing Eicosanoids of Marine Origin. Biomimetic Synthesis of Constanolactones A and B from the Alga Constantinea simplex

  摘要：

  Asymmetric syntheses of 7, a substance isolated from incubation of arachidonic acid with an acetone powder of the coral Plexaura homomalla, and of constanolactones A (9) and B (10), metabolites of the red alga Constantinea simplex, are described. The key step involves stannic chloride-mediated cyclization of the oxirane derived from Sharpless epoxidation of 10-hydroxy-5,8-decadienoates, and is shown to yield a trans disubstituted cyclopropane Linked to a delta-lactone. Both (R) and (S) configurations at C5 of the lactone are produced in the cyclization, the ratio being independent of olefin geometry in the acyclic precursor, Elaboration of the cyclization products via Nozaki-Kishi coupling of the derived aldehydes 26 and 37 with the appropriate (1E,5Z)-1-iodo-1,5-undecadiene led to 7, 9, and 10, thereby establishing the relative configuration of 7 and confirming the absolute configuration of 9 and 10.

  DOI：

  10.1021/ja00128a008

文献信息

• Deblocking of dithioacetals and oxathioacetals using periodic acid under mild nonaqueous conditions
  作者：Xiao-Xin Shi、Subhash P. Khanapure、Joshua Rokach

  DOI：10.1016/0040-4039(96)00838-6

  日期：1996.6

  A novel method for the deblocking of the dithioacetals and oxathioacetals is described. Periodic acid under nonaqueous conditions has been used for the deprotection of the dithio- and oxathio-derivatives to the corresponding carbonyl compounds. This simple high-yield transformation is conveniently carried out in nonaqueous medium and works well with complex sensitive aldehydes and in the presence of

  描述了用于解封二硫缩醛和草硫缩醛的新方法。非水条件下的高碘酸已用于将二硫代和氧杂硫代衍生物脱保护为相应的羰基化合物。这种简单的高收率转化可在非水介质中方便地进行，并且与复杂的敏感醛以及存在其他保护基时均能很好地发挥作用。
• The total syntheses of several 8, 15 dihydroxy arachidonic acid derivatives (8,15, LTB's)
  作者：Brian J. Fitzsimmons、Joshua Rokach

  DOI：10.1016/0040-4039(84)80003-9

  日期：——

  The synthesis of the 8S, 15S and 8R, 15S diastereomers of 8,15 dihydroxy 5Z,9E,11E,13Z eicosatetraenoic acid (8,15-LTB4) and of 8,15 dihydroxy 5Z,9E,11Z,13E eicosatetraenoic acid (8,15-LTBx) from arabinose are described.

  8,15二羟基5Z，9E，11E，13Z二十碳四烯酸（8,15-LTB 4）和8,15二羟基5Z，9E，11Z，13E二十碳四烯酸（8S，15S和8R，15S非对映异构体的合成描述了来自阿拉伯糖的8,15-LTB x）。
• A simple synthesis of methyl 11(s)- and 12(s)-hete
  作者：George Just、Zhi Yuan Wang

  DOI：10.1016/s0040-4039(00)98600-3

  日期：1985.1

  Starting from D-arabinose, we describe a synthesis of 11S and 12S-HETE methyl esters.

  从D-阿拉伯糖开始，我们描述了11S和12S-HETE甲酯的合成。
• First total synthesis of pro-resolving and tissue-regenerative resolvin sulfido-conjugates
  作者：Ana R. Rodriguez、Bernd W. Spur

  DOI：10.1016/j.tetlet.2017.03.041

  日期：2017.4

  The first total synthesis of the pro-resolving and tissue-regenerative resolvin sulfido-conjugates: 7S,8R,17S-RCTR1, 7S,8R,17S-RCTR2 and 7S,8R,17S-RCTR3, derived from docosahexaenoic acid, has been achieved. Two synthetic approaches are described. Chiral centers 7S and 8R were introduced in both approaches via a chiral pool strategy starting from 2-deoxy-d-ribose. The 17S chiral center was introduced

  促分辨和组织再生性RESOLVIN硫键结合物的第一个全合成：7 S，8 R，17 S -RCTR1，7 S，8 R，17 S -RCTR2和7 S，8 R，17 S -RCTR3已经获得了源自二十二碳六烯酸的化合物。描述了两种合成方法。手性中心7小号和8 - [R在两个引入通过从2-脱氧起始手性池策略接近d -核糖。17 S通过手性池策略或通过脂氧化酶的酶促羟基化引入手性中心。Wittig反应，分别与谷胱甘肽，1-半胱氨酰甘氨酸和1-半胱氨酸的选择性环氧化物形成和环氧化物打开是合成的关键步骤。
• The total synthesis of 12-HETE (12-hydroxyeicosatetraenoic acid) and 12,20-diHETE
  作者：Yves Leblanc、Brian J. Fitzsimmons、Julian Adams、Francoise Perez、Joshua Rokach

  DOI：10.1021/jo00356a004

  日期：1986.3