[(4R,5R)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]methyl trifluoromethanesulfonate | 528598-38-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: [(4R,5R)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]methyl trifluoromethanesulfonate
• CAS: 528598-38-1
• 化学式: C₁₄H₂₇F₃O₆SSi
• 分子量: 408.511
• InChiKey: MDBORAKCTLZHIC-GHMZBOCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.39
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  79.4
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  [(4R,5R)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]methyl trifluoromethanesulfonate 在 Wilkinson's catalyst 正丁基锂 、 四丁基氟化铵 、 氢气 、 三乙胺 、 copper(I) bromide 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 苯 为溶剂， 生成 (4R,5R)-4-[(5S)-5,7-bis(phenylmethoxy)heptyl]-5-but-3-enyl-2,2-dimethyl-1,3-dioxolane
  参考文献：
  名称：

  Total Synthesis of a Cytotoxic Acetogenin, Pyranicin

  摘要：

  The first total synthesis of a new cytotoxic acetogenin, pyranicin (1), is described. SmI2-induced reductive cyclization of beta-alkoxy acrylate 4 proceeded stereoselectively to give 16,20-syn,-19,20-trans-THP derivative 14, which was efficiently transformed into the 19,20-cis-THP derivative 18 through Mitsunobu lactonization. Wittig reaction of the phosphonium salt 2 obtained therefrom with butenolide 3 at -78 degreesC followed by reduction and deprotection afforded 1 in good overall yield.

  DOI：

  10.1021/ol034323m
• 作为产物：
  描述：

  (-)-2,3-O-亚异丙基-D-苏力糖醇 在 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 二氯甲烷 为溶剂， 生成 [(4R,5R)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]methyl trifluoromethanesulfonate
  参考文献：
  名称：

  Total Synthesis of a Cytotoxic Acetogenin, Pyranicin

  摘要：

  The first total synthesis of a new cytotoxic acetogenin, pyranicin (1), is described. SmI2-induced reductive cyclization of beta-alkoxy acrylate 4 proceeded stereoselectively to give 16,20-syn,-19,20-trans-THP derivative 14, which was efficiently transformed into the 19,20-cis-THP derivative 18 through Mitsunobu lactonization. Wittig reaction of the phosphonium salt 2 obtained therefrom with butenolide 3 at -78 degreesC followed by reduction and deprotection afforded 1 in good overall yield.

  DOI：

  10.1021/ol034323m

文献信息

• [EN] BRANCHED SUGAR ALCOHOL-BASED COMPOUNDS, AND COMPOSITIONS AND METHODS THEREOF<br/>[FR] COMPOSÉS À BASE D'ALCOOL DE SUCRE RAMIFIÉ, ET COMPOSITIONS ET PROCÉDÉS ASSOCIÉS
  申请人：CELLMOSAIC INC

  公开号：WO2019213046A1

  公开（公告）日：2019-11-07

  The invention provides novel sugar alcohol-based dendrimer-like molecules. These sugar alcohol-based molecules have multiple functional groups that can be used to label, conjugate, and immobilize large amounts of molecules or multiple types of molecules of interest for diagnostic, therapeutic, and research usage. Methods of synthesizing these sugar alcohol-based dendrimer-like molecules and conjugates are also within the scope of the invention.

  这项发明提供了新型基于糖醇的树状分子。这些基于糖醇的分子具有多个功能基团，可用于标记、结合和固定大量或多种感兴趣的分子，用于诊断、治疗和研究用途。合成这些基于糖醇的树状分子和结合物的方法也属于该发明的范围内。
• Total Synthesis of a Cytotoxic Acetogenin, Pyranicin
  作者：Shunya Takahashi、Akemi Kubota、Tadashi Nakata

  DOI：10.1021/ol034323m

  日期：2003.4.1

  The first total synthesis of a new cytotoxic acetogenin, pyranicin (1), is described. SmI2-induced reductive cyclization of beta-alkoxy acrylate 4 proceeded stereoselectively to give 16,20-syn,-19,20-trans-THP derivative 14, which was efficiently transformed into the 19,20-cis-THP derivative 18 through Mitsunobu lactonization. Wittig reaction of the phosphonium salt 2 obtained therefrom with butenolide 3 at -78 degreesC followed by reduction and deprotection afforded 1 in good overall yield.