3-O-tert-butyldimethylsilyl-2-O-chloroacetyl-4,6-O-isopropylidene-D-glucopyranose 1-trichloroacetimidate | 1130996-26-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: 3-O-tert-butyldimethylsilyl-2-O-chloroacetyl-4,6-O-isopropylidene-D-glucopyranose 1-trichloroacetimidate
• 英文别名: [(4aR,6S,7R,8S,8aR)-8-[tert-butyl(dimethyl)silyl]oxy-2,2-dimethyl-6-(2,2,2-trichloroethanimidoyl)oxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl] 2-chloroacetate
• CAS: 1130996-26-7
• 化学式: C₁₉H₃₁Cl₄NO₇Si
• 分子量: 555.355
• InChiKey: RRNQMLYHQXLOJV-LFHLZQBKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.77
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  96.3
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-nonen-4S-yl 4-O-acetyl-3-O-benzyl-β-D-fucopyranoside 、 3-O-tert-butyldimethylsilyl-2-O-chloroacetyl-4,6-O-isopropylidene-D-glucopyranose 1-trichloroacetimidate 在 三氟化硼乙醚 作用下， 以 二氯甲烷 、 环己烷 为溶剂， 以52%的产率得到[(4aR,6S,7R,8S,8aR)-6-[(2R,3R,4S,5S,6R)-5-acetyloxy-6-methyl-2-[(4S)-non-1-en-4-yl]oxy-4-phenylmethoxyoxan-3-yl]oxy-8-[tert-butyl(dimethyl)silyl]oxy-2,2-dimethyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl] 2-chloroacetate
  参考文献：
  名称：

  Total Synthesis of Ipomoeassin F

  摘要：

  The first total synthesis of ipomoeassin F was carried out using a convergent approach that relied upon the use of Schmidt glycosidation technology for the coupling of two suitably protected monosaccharide fragments. After two steps, ring-closing metathesis was used to form the macrocyclic ring, and seven more steps then furnished ipomoeassin F. In vitro inhibitory activity against a four-panel cell line showed low nanomolar inhibitory activity.

  DOI：

  10.1021/ol900086b
• 作为产物：
  描述：

  3-O-tert-butyldimethylsilyl-2-O-chloroacetyl-4,6-O-isopropylidene-D-glucopyranose 、 三氯乙腈 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 生成 3-O-tert-butyldimethylsilyl-2-O-chloroacetyl-4,6-O-isopropylidene-D-glucopyranose 1-trichloroacetimidate 、 3-O-tert-butyldimethylsilyl-2-O-chloroacetyl-4,6-O-isopropylidene-D-glucopyranose 1-trichloroacetimidate
  参考文献：
  名称：

  Total Synthesis of Ipomoeassin F

  摘要：

  The first total synthesis of ipomoeassin F was carried out using a convergent approach that relied upon the use of Schmidt glycosidation technology for the coupling of two suitably protected monosaccharide fragments. After two steps, ring-closing metathesis was used to form the macrocyclic ring, and seven more steps then furnished ipomoeassin F. In vitro inhibitory activity against a four-panel cell line showed low nanomolar inhibitory activity.

  DOI：

  10.1021/ol900086b

文献信息

• Total Synthesis of Ipomoeassin F
  作者：Maarten H. D. Postema、Karen TenDyke、James Cutter、Galina Kuznetsov、Qunli Xu

  DOI：10.1021/ol900086b

  日期：2009.3.19

  The first total synthesis of ipomoeassin F was carried out using a convergent approach that relied upon the use of Schmidt glycosidation technology for the coupling of two suitably protected monosaccharide fragments. After two steps, ring-closing metathesis was used to form the macrocyclic ring, and seven more steps then furnished ipomoeassin F. In vitro inhibitory activity against a four-panel cell line showed low nanomolar inhibitory activity.