Trifluoro-methanesulfonic acid (4R,5R)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester | 133842-56-5

• 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: Trifluoro-methanesulfonic acid (4R,5R)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester
• 英文别名: [(4R,5R)-2,2-dimethyl-5-(phenylmethoxymethyl)-1,3-dioxolan-4-yl]methyl trifluoromethanesulfonate
• CAS: 133842-56-5
• 化学式: C₁₅H₁₉F₃O₆S
• 分子量: 384.373
• InChiKey: CKBSRAOARCGHKZ-CHWSQXEVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  Trifluoro-methanesulfonic acid (4R,5R)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester 在 四氧化锇 N-甲基吗啉 、 甲醇 、 sodium periodate 、 samarium diiodide 、 D(+)-10-樟脑磺酸 、 四丁基碘化铵 、 zinc trifluoromethanesulfonate 、 sodium hydride 、 碳酸氢钠 、 copper(I) bromide 、 碘甲烷 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 水 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 、 乙腈 、 叔丁醇 为溶剂， 反应 74.25h， 生成 (2'R,3'S,6'R,1''R)-[6'-(1'',2''-bis-benzyloxy-ethyl)-3'-hydroxy-tetrahydropyran-2'-yl]-acetic acid ethyl ester
  参考文献：
  名称：

  Total Synthesis of the Proposed Structure for Pyragonicin

  摘要：

  The total synthesis of acetogenin 1 reported for pyragonicin and its 10-epimer 32 is described. The common THP ring system was stereoselectively constructed through a SMI2-induced reductive cyclization of beta-alkoxy acrylate 5 followed by Mitsunobu inversion, and each chiral center at C-10 was created by Brown's asymmetric allylation. Compound 1 had spectroscopic data consistent with that of natural pyragonicin, but a different optical rotation.

  DOI：

  10.1021/ol0508126
• 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 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 Trifluoro-methanesulfonic acid (4R,5R)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester
  参考文献：
  名称：

  Total Synthesis of the Proposed Structure for Pyragonicin

  摘要：

  The total synthesis of acetogenin 1 reported for pyragonicin and its 10-epimer 32 is described. The common THP ring system was stereoselectively constructed through a SMI2-induced reductive cyclization of beta-alkoxy acrylate 5 followed by Mitsunobu inversion, and each chiral center at C-10 was created by Brown's asymmetric allylation. Compound 1 had spectroscopic data consistent with that of natural pyragonicin, but a different optical rotation.

  DOI：

  10.1021/ol0508126

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。
• JPH032158A
  申请人：——

  公开号：JPH032158A

  公开（公告）日：1991-01-08
• Total Synthesis of the Proposed Structure for Pyragonicin
  作者：Shunya Takahashi、Narihito Ogawa、Hiroyuki Koshino、Tadashi Nakata

  DOI：10.1021/ol0508126

  日期：2005.6.1

  The total synthesis of acetogenin 1 reported for pyragonicin and its 10-epimer 32 is described. The common THP ring system was stereoselectively constructed through a SMI2-induced reductive cyclization of beta-alkoxy acrylate 5 followed by Mitsunobu inversion, and each chiral center at C-10 was created by Brown's asymmetric allylation. Compound 1 had spectroscopic data consistent with that of natural pyragonicin, but a different optical rotation.