2-(1',3',4',6'-tetra-O-benzylfructofuranosyl)-2-propene | 111085-79-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(1',3',4',6'-tetra-O-benzylfructofuranosyl)-2-propene
• 英文别名: 1-(1,3,4,6-tetra-O-benzyl-α-D-fructofuranosyl)-2-propene；(2S,3S,4R,5R)-3,4-bis(phenylmethoxy)-2,5-bis(phenylmethoxymethyl)-2-prop-2-enyloxolane
• CAS: 111085-79-1
• 化学式: C₃₇H₄₀O₅
• 分子量: 564.722
• InChiKey: BWZOPOQVQIYDRY-MDOFDWFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  42
• 可旋转键数：
  16
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(1',3',4',6'-tetra-O-benzylfructofuranosyl)-2-propene 生成 1-(1,3,4,6-tetra-O-benzyl-α-D-fructofuranosyl)-1-propene
  参考文献：
  名称：

  NICOTRA, FRANCESCO;PANZA, LUIGI;RUSSO, GIOVANNI, J. ORG. CHEM., 52,(1987) N 25, 5627-5630

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl D-fructofuranoside 在 三氟化硼乙醚 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-(1',3',4',6'-tetra-O-benzylfructofuranosyl)-2-propene
  参考文献：
  名称：

  Polycyclic scaffolds from fructose

  摘要：

  Iodocyclisation of polybenzylated allyl alpha-C-fructofuranoside 1 afforded the bicyclic iodoether 2 through debenzylation at C-1: treatment of 2 with zinc and acetic acid restored the all tic group with concomitant deprotection of the hydroxyl group ;at C-1, which as oxidised to the corresponding aldehyde 4. Reaction of 4 with vinylmagnesium bromide afforded diene 5, whose double bonds were reacted regioselectively in order to obtain, upon iodocylisation under different experimental conditions. bicycles 6 or 7, or tricycle 8. (C) 2002 Elsevier Science Ltd. All rights reserve.

  DOI：

  10.1016/s0040-4039(01)02393-0

文献信息

• Synthesis of bicyclic sugar azido acids and their incorporation in cyclic peptides
  作者：Francesco Peri、Laura Cipolla、Barbara La Ferla、F. Nicotra

  DOI：10.1039/b006192l

  日期：——

  Bicyclic amino acids derived from the natural sugars D-arabinofuranose and D-fructofuranose have been synthesised; their ability to induce a turn conformation in peptides has been exploited in the preparation of a cyclic RGD loop mimetic.

  已合成源自天然糖 D-阿拉伯呋喃糖和 D-呋喃果糖的双环氨基酸；它们在肽中诱导转角构象的能力已被用于制备环状 RGD 环模拟物。
• Substrate-directed asymmetric induction in the rhodium catalyzed hydroformylation of C-allyl-sugars: The influence of the glycoside-moiety on the selectivity of the reaction
  作者：Raffaello Lazzaroni、Silvia Rocchiccioli、Anna Iuliano、Laura Cipolla

  DOI：10.1016/j.jorganchem.2006.06.008

  日期：2006.9

  depending on the starting alkene. The results obtained have allowed us to study the influence of the different structural features of the sugar moiety on the regio- and diastereoselectivity of the hydroformylation reaction.

  在低温下将α-和β-C-烯丙基半乳糖吡喃糖苷1c和1d，α-C-烯丙基吡喃葡萄糖苷1e和α-C-烯丙基呋喃呋喃糖苷1f加氢甲酰化，得到线性和支链醛的区域异构体和非对映异构体比例的混合物，取决于起始烯烃。获得的结果使我们能够研究糖部分的不同结构特征对加氢甲酰化反应的区域和非对映选择性的影响。
• Synthesis and Conformational Analysis of Fructose-Derived Scaffolds: Molecular Diversity from a Single Molecule
  作者：Laura Cipolla、Eleonora Forni、Jesus Jiménez-Barbero、Francesco Nicotra

  DOI：10.1002/1521-3765(20020902)8:17<3976::aid-chem3976>3.0.co;2-7

  日期：2002.9.2

  and tricyclic compounds were synthesized starting from fructose. The different hydroxyl groups present in fructose were exploited in the formation of a number of conformationally constrained sugar-based scaffolds, including azido acids. Introduction of an azido group and carboxy terminus into different bicyclic iodo ethers, allowed the synthesis of different conformationally constrained azido acids.

  从果糖开始合成双环和三环化合物。果糖中存在的不同羟基被用于形成许多构象受限的糖基支架，包括叠氮酸。将叠氮基和羧基末端引入不同的双环碘醚中，可以合成不同的构象约束叠氮酸。通过分子力学协助的NMR实验对化合物10、11、17和20进行构象分析，可以确定相关官能团之间的距离，即叠氮基和羧基官能团。
• Stereoselective access to .alpha.- and .beta.-D-fructofuranosyl C-glycosides
  作者：Francesco Nicotra、Luigi Panza、Giovanni Russo

  DOI：10.1021/jo00234a024

  日期：1987.12