(Z)-1-(benzyl 2,3-O-isopropylidene-β-D-ribo-tetrafuranosid-4-yl)-2-(1,2:3,4-di-O-isopropylidene-α-D-galacto-pentopyranos-5-yl)ethylene

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: (Z)-1-(benzyl 2,3-O-isopropylidene-β-D-ribo-tetrafuranosid-4-yl)-2-(1,2:3,4-di-O-isopropylidene-α-D-galacto-pentopyranos-5-yl)ethylene
• 英文别名: (1S,2R,6R,8R,9S)-8-[(Z)-2-[(3aR,4R,6R,6aR)-2,2-dimethyl-4-phenylmethoxy-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]ethenyl]-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecane
• 化学式: C₂₇H₃₆O₉
• 分子量: 504.577
• InChiKey: HDWXGVLJARJJRZ-YTZGVHKZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  36
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  83.1
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (Z)-1-(benzyl 2,3-O-isopropylidene-β-D-ribo-tetrafuranosid-4-yl)-2-(1,2:3,4-di-O-isopropylidene-α-D-galacto-pentopyranos-5-yl)ethylene 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  Simple approach to O-protected deaminotunicaminyluracil

  摘要：

  A five-step synthesis of deaminotunieaminyluracil is presented. Coupling of the ylide, generated from the phosphonium salt 4, with the aldehyde 5 afforded the undecose 6 in high yield. The key step in this synthesis was the hydroboration-oxidation reaction of the olefin 6. For this purpose several hydroborating reagents were examined. The diborane-THF reagent led to the desired deaminotunicamine derivative 8, as the predominant product. Condensation of undecose 8c with 1,3-di-O-trimethylsilyluracil gave the title compound.

  DOI：

  10.1016/s0040-4020(01)87008-3
• 作为产物：
  描述：

  6-脱氧-6-碘-1,2:3,4-二-o-异亚丙基-α-d-半乳糖吡喃糖苷 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 甲苯 为溶剂， 反应 21.0h， 生成 (Z)-1-(benzyl 2,3-O-isopropylidene-β-D-ribo-tetrafuranosid-4-yl)-2-(1,2:3,4-di-O-isopropylidene-α-D-galacto-pentopyranos-5-yl)ethylene
  参考文献：
  名称：

  Simple approach to O-protected deaminotunicaminyluracil

  摘要：

  A five-step synthesis of deaminotunieaminyluracil is presented. Coupling of the ylide, generated from the phosphonium salt 4, with the aldehyde 5 afforded the undecose 6 in high yield. The key step in this synthesis was the hydroboration-oxidation reaction of the olefin 6. For this purpose several hydroborating reagents were examined. The diborane-THF reagent led to the desired deaminotunicamine derivative 8, as the predominant product. Condensation of undecose 8c with 1,3-di-O-trimethylsilyluracil gave the title compound.

  DOI：

  10.1016/s0040-4020(01)87008-3

文献信息

• Simple approach to O-protected deaminotunicaminyluracil
  作者：Wojciech Karpiesiuk、Anna Banaszek

  DOI：10.1016/s0040-4020(01)87008-3

  日期：1994.2

  A five-step synthesis of deaminotunieaminyluracil is presented. Coupling of the ylide, generated from the phosphonium salt 4, with the aldehyde 5 afforded the undecose 6 in high yield. The key step in this synthesis was the hydroboration-oxidation reaction of the olefin 6. For this purpose several hydroborating reagents were examined. The diborane-THF reagent led to the desired deaminotunicamine derivative 8, as the predominant product. Condensation of undecose 8c with 1,3-di-O-trimethylsilyluracil gave the title compound.