1-nonen-4S-yl 4-O-acetyl-3-O-benzyl-β-D-fucopyranoside | 1130996-48-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-nonen-4S-yl 4-O-acetyl-3-O-benzyl-β-D-fucopyranoside
• 英文别名: [(2R,3S,4R,5R,6R)-5-hydroxy-2-methyl-6-[(4S)-non-1-en-4-yl]oxy-4-phenylmethoxyoxan-3-yl] acetate
• CAS: 1130996-48-3
• 化学式: C₂₄H₃₆O₆
• 分子量: 420.546
• InChiKey: FTHYCRAZTQSQAF-FMYUWVRYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  30
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

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：

  1-nonen-4S-yl 4-O-acetyl-3-O-benzyl-2-O-tert-butyldimethylsilyl-β-D-fucopyranoside 在 盐酸 作用下， 以 甲醇 为溶剂， 以3.55 g的产率得到1-nonen-4S-yl 4-O-acetyl-3-O-benzyl-β-D-fucopyranoside
  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