(1R,2S,4S,5S,7R,10R)-10-phenyl-5-prop-2-enoxy-3,6,9,11-tetraoxatricyclo[5.4.0.02,4]undecane | 623148-35-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧环庚烷
• 英文名称: (1R,2S,4S,5S,7R,10R)-10-phenyl-5-prop-2-enoxy-3,6,9,11-tetraoxatricyclo[5.4.0.02,4]undecane
• CAS: 623148-35-6
• 化学式: C₁₆H₁₈O₅
• 分子量: 290.316
• InChiKey: AWQQLGRJAAZPNZ-XMEMRUQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  49.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1R,2S,4S,5S,7R,10R)-10-phenyl-5-prop-2-enoxy-3,6,9,11-tetraoxatricyclo[5.4.0.02,4]undecane 在 palladium diacetate 、 双(三甲基硅烷基)氨基钾 、 二乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 6.75h， 生成 ethyl (E)-3-[(2R,3R)-3-[(2R,4R,5R)-5-hydroxy-2-phenyl-1,3-dioxan-4-yl]oxiran-2-yl]prop-2-enoate
  参考文献：
  名称：

  A Versatile and Stereocontrolled Route to Pyranose and Furanose C-Glycosides

  摘要：

  The alpha,beta-unsaturated-gamma,delta-epoxyester 1 is a novel and versatile precursor to a wide variety of C-glycosides. For instance, treatment of Z-1 or E-1 with palladium(0) affords, stereospecifically, beta- or alpha-C-furanosides, respectively. In contrast, reaction of Z-1 or E-1 with base gives, stereoselectively, the beta- or alpha-C-pyranosides, respectively.

  DOI：

  10.1021/ol0490678
• 作为产物：
  描述：

  2-PROPENYL4,6-O-BENZYLIDENE-Α-D-GLUCOPYRANOSIDE2-丙烯基4,6-O-亚苄基-Α-D-吡喃葡萄糖苷 在 sodium hydride 、 1-对甲基苯磺酰咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.5h， 以75%的产率得到(1R,2S,4S,5S,7R,10R)-10-phenyl-5-prop-2-enoxy-3,6,9,11-tetraoxatricyclo[5.4.0.02,4]undecane
  参考文献：
  名称：

  A Versatile and Stereocontrolled Route to Pyranose and Furanose C-Glycosides

  摘要：

  The alpha,beta-unsaturated-gamma,delta-epoxyester 1 is a novel and versatile precursor to a wide variety of C-glycosides. For instance, treatment of Z-1 or E-1 with palladium(0) affords, stereospecifically, beta- or alpha-C-furanosides, respectively. In contrast, reaction of Z-1 or E-1 with base gives, stereoselectively, the beta- or alpha-C-pyranosides, respectively.

  DOI：

  10.1021/ol0490678

文献信息

• Thieme Chemistry Journal Awardees - Where Are They Now? Approaches to Tagetitoxin and its Decarboxy Analogue from d-Glucose
  作者：Michael Porter、Julien Plet、Amandeep Sandhu、Moussa Sehailia

  DOI：10.1055/s-0029-1218525

  日期：2009.12

  A fifteen-step route has been developed from 1,6-anhydro-beta-D-glucopyranose to a C-alkynyl glycoside precursor of decarboxytagetitoxin. Preparation of 1,6-anhydro-5-C-vinyl-beta-D-glucopyranose, a potential precursor of tagetitoxin, is also described.

  已开发出从 1,6-脱水-β-D-吡喃葡萄糖到脱羧万寿菊毒素的 C-炔基糖苷前体的十五步路线。还描述了 1,6-脱水-5-C-乙烯基-β-D-吡喃葡萄糖，一种潜在的 tagetitoxin 前体的制备。
• A Versatile and Stereocontrolled Route to Pyranose and Furanose <i>C</i>-Glycosides
  作者：Joanne E. Harvey、Steven A. Raw、Richard J. K. Taylor

  DOI：10.1021/ol0490678

  日期：2004.7.1

  The alpha,beta-unsaturated-gamma,delta-epoxyester 1 is a novel and versatile precursor to a wide variety of C-glycosides. For instance, treatment of Z-1 or E-1 with palladium(0) affords, stereospecifically, beta- or alpha-C-furanosides, respectively. In contrast, reaction of Z-1 or E-1 with base gives, stereoselectively, the beta- or alpha-C-pyranosides, respectively.