3-formylpropyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside | 173206-23-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 3-formylpropyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside
• 英文别名: But-4-al-1-yl-2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside；4-[(2R,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxybutanal
• CAS: 173206-23-0
• 化学式: C₃₈H₄₂O₇
• 分子量: 610.747
• InChiKey: HUMZOURMEAWUSX-JTDOPDNRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  45
• 可旋转键数：
  18
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-formylpropyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 0.17h， 以84%的产率得到4-Hydroxybut-1-yl-2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of a symmetric multivalent molecule containing four carbohydrate substituents

  摘要：

  Starting with allyl- and pent-4-enyl-beta-D-glucopyranosides 4-7, different D-Glucose units (8-15) containing alkyl spacers of variable lenght and with different end groups can be prepared. Reaction of four equivalents of the caesium salt derived from propan-4-carboxy-1-yl-2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside 15 with pentaerythrityltetrabromide yields the tetravalent molecule 16.

  DOI：

  10.1007/bf00811012
• 作为产物：
  描述：

  4-戊烯-1-基2,3,4,6-四-O-苄基-D-吡喃葡萄糖苷 在 臭氧 、 三苯基膦 作用下， 生成 3-formylpropyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of a symmetric multivalent molecule containing four carbohydrate substituents

  摘要：

  Starting with allyl- and pent-4-enyl-beta-D-glucopyranosides 4-7, different D-Glucose units (8-15) containing alkyl spacers of variable lenght and with different end groups can be prepared. Reaction of four equivalents of the caesium salt derived from propan-4-carboxy-1-yl-2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside 15 with pentaerythrityltetrabromide yields the tetravalent molecule 16.

  DOI：

  10.1007/bf00811012

文献信息

• Use of <i>n</i>-Pentenyl Glycosides as Precursors to Various Spacer Functionalities
  作者：Therese Buskas、Eva Söderberg、Peter Konradsson、Bert Fraser-Reid

  DOI：10.1021/jo9909554

  日期：2000.2.1

  Pent-4-enyl beta-D-glucopyranoside and its peracetylated and perbenzylated derivatives are shown to be excellent substrates for preparation of a wide variety of spacer functionalities. The spacer derivatives so obtained are promising substrates for preparing agents such as neo-glycoconjugates, micelles, and liquid crystalline phases, which are of interest for studying various biological and physiological phenomena of carbohydrates.
• Synthesis of a symmetric multivalent molecule containing four carbohydrate substituents
  作者：W. H. Binder、W. Schmid

  DOI：10.1007/bf00811012

  日期：——

  Starting with allyl- and pent-4-enyl-beta-D-glucopyranosides 4-7, different D-Glucose units (8-15) containing alkyl spacers of variable lenght and with different end groups can be prepared. Reaction of four equivalents of the caesium salt derived from propan-4-carboxy-1-yl-2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside 15 with pentaerythrityltetrabromide yields the tetravalent molecule 16.