[(2R,3R,4R,5S)-4-benzoyloxy-5-(4-methylphenyl)sulfanyl-2-[tri(propan-2-yl)silyloxymethyl]oxolan-3-yl] benzoate | 1067674-44-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2R,3R,4R,5S)-4-benzoyloxy-5-(4-methylphenyl)sulfanyl-2-[tri(propan-2-yl)silyloxymethyl]oxolan-3-yl] benzoate
• CAS: 1067674-44-5
• 化学式: C₃₅H₄₄O₆SSi
• 分子量: 620.882
• InChiKey: PRFVGGISFVKYBF-CDNMXTEVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.46
• 重原子数：
  43
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  96.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-[(3aR,4R,6R,6aR)-6-(hydroxymethyl)spiro[3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole-2,1'-cyclopentane]-4-yl]-3-(phenylmethoxymethyl)pyrimidine-2,4-dione 、 [(2R,3R,4R,5S)-4-benzoyloxy-5-(4-methylphenyl)sulfanyl-2-[tri(propan-2-yl)silyloxymethyl]oxolan-3-yl] benzoate 在 strontium(II) carbonate 、 silver trifluoromethanesulfonate 、 p-toluolsulfenyl bromide 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 0.5h， 以95%的产率得到[(2R,3R,4R,5R)-5-[[(3aR,4R,6R,6aR)-4-[2,4-dioxo-3-(phenylmethoxymethyl)pyrimidin-1-yl]spiro[3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole-2,1'-cyclopentane]-6-yl]methoxy]-4-benzoyloxy-2-[tri(propan-2-yl)silyloxymethyl]oxolan-3-yl] benzoate
  参考文献：
  名称：

  Highly Efficient O-Glycosylations with p-Tolyl Thioribosides and p-TolSOTf

  摘要：

  GraphicsA wide variety of p-tolyl thioriboside donors are examined for O-ribosylations of primary and secondary alcohols. p-Tolylsulfenyl trifluoromethanesulfonate (p-TolSOTf) is very effective in promoting O-ribosylations with p-tolyl thioriboside; all reactions are completed within 1-15 min to provide the desired products in good yield with reliable alpha/beta selectivity. A wide range of functional groups are tolerated under these conditions. The described O-ribosylation conditions are very useful for the generation of ribosaminouridine library molecules in solution or on polymer support.

  DOI：

  10.1021/jo801408x
• 作为产物：
  描述：

  苯甲酰氯 、 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 以60%的产率得到
  参考文献：
  名称：

  通过电化学环化完全合成 Dragocins A−C

  摘要：

  利用电化学环化在杂化代谢物 dragocins A-C 中锻造中心 9 元环。该路线具有几个立体对照反应，以解决吡咯烷片段的立体四分体，以及倒数第二个脱羧氯化和整体脱保护，以提供 dragocin B 和 C。

  DOI：

  10.1002/anie.202401107

文献信息

• Highly Efficient <i>O</i>-Glycosylations with <i>p</i>-Tolyl Thioribosides and <i>p</i>-TolSOTf
  作者：Michio Kurosu、Kai Li

  DOI：10.1021/jo801408x

  日期：2008.12.19

  GraphicsA wide variety of p-tolyl thioriboside donors are examined for O-ribosylations of primary and secondary alcohols. p-Tolylsulfenyl trifluoromethanesulfonate (p-TolSOTf) is very effective in promoting O-ribosylations with p-tolyl thioriboside; all reactions are completed within 1-15 min to provide the desired products in good yield with reliable alpha/beta selectivity. A wide range of functional groups are tolerated under these conditions. The described O-ribosylation conditions are very useful for the generation of ribosaminouridine library molecules in solution or on polymer support.
• Total Synthesis of Dragocins A−C through Electrochemical Cyclization
  作者：Brendyn P. Smith、Nathanyal J. Truax、Alexandros S. Pollatos、Michael Meanwell、Pranali Bedekar、Alberto F. Garrido‐Castro、Phil S. Baran

  DOI：10.1002/anie.202401107

  日期：2024.5.6

  An electrochemical cyclization is leveraged to forge the central 9-membered ring in the hybrid metabolites dragocins A−C. The route features several stereocontrolled reactions to address the stereotetrad of the pyrrolidine fragment and a penultimate decarboxylative chlorination and global deprotection to furnish both dragocins B and C. Dragocin A was prepared through simple methanolysis of dragocin

  利用电化学环化在杂化代谢物 dragocins A-C 中锻造中心 9 元环。该路线具有几个立体对照反应，以解决吡咯烷片段的立体四分体，以及倒数第二个脱羧氯化和整体脱保护，以提供 dragocin B 和 C。