3-O-benzyl-1,2-O-isopropylidene-5-C-phenyl-α-D-xylo-pent-5-ulo-furanose | 20715-20-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-O-benzyl-1,2-O-isopropylidene-5-C-phenyl-α-D-xylo-pent-5-ulo-furanose
• CAS: 20715-20-2
• 化学式: C₂₁H₂₂O₅
• 分子量: 354.403
• InChiKey: OJTIIKFSNQVGII-IYWMVGAKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.33
• 重原子数：
  26.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  53.99
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3-O-benzyl-1,2-O-isopropylidene-5-C-phenyl-α-D-xylo-pent-5-ulo-furanose 在 palladium on activated charcoal 吡啶 、 sodium tetrahydroborate 、 cerium(III) chloride 、 氢气 、 溴 、 sodium hydride 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 barium carbonate 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 甲醇 、 乙醚 、 水 、 乙腈 为溶剂， 反应 105.75h， 生成 (+)-goniofufurone
  参考文献：
  名称：

  The total synthesis of Goniofufurone

  摘要：

  The total synthesis of natural (+)-Goniofufurone and related compounds from D-glucose is reported utilising a non-classical Wittig reaction. The factors governing the epimerisation of the tetronate 7 are also discussed.

  DOI：

  10.1016/s0040-4020(01)81838-x
• 作为产物：
  描述：

  3-O-benzyl-1,2-O-isopropylidene-5-C-phenyl-α-L-ido-pentofuranose 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 生成 3-O-benzyl-1,2-O-isopropylidene-5-C-phenyl-α-D-xylo-pent-5-ulo-furanose
  参考文献：
  名称：

  The total synthesis of Goniofufurone

  摘要：

  The total synthesis of natural (+)-Goniofufurone and related compounds from D-glucose is reported utilising a non-classical Wittig reaction. The factors governing the epimerisation of the tetronate 7 are also discussed.

  DOI：

  10.1016/s0040-4020(01)81838-x

文献信息

• Ethoxycarbonylmethylenetriphenylphosphorane in carbohydrate chemistry, part II: a short and efficient synthesis of (+)-goniofufurone
  作者：K.R.C. Prakash、S.Prahlada Rao

  DOI：10.1016/s0040-4020(01)90202-9

  日期：1993.2

  A concise approach to the synthesis of anti-tumor compound, goniofufurone is described starting from dialdo-xylose. The key step in our synthesis is the spontaneous lactonisation and Michael-ring closure accompanying the Wittig reaction of the title ylide with the furanose-lactol having a free hydroxyl group at C-2.

  从二糖木糖开始描述了一种合成抗肿瘤化合物goniofufurone的简明方法。我们合成过程中的关键步骤是自发的内酯化作用和Michael环的闭合，伴随着标题内酯与在C-2处具有游离羟基的呋喃糖-内酯的Wittig反应。
• A synthesis of goniofufurone
  作者：P. J. Murphy

  DOI：10.1039/c39920001096

  日期：——

  The total synthesis of natural (+)-goniofufurone from D-glucose is reported.

  报告了从 D-葡萄糖全合成天然 (+)-goniofufurone 的过程。
• Asymmetric synthesis of (+)-cardiobutanolide
  作者：Ashish Garg、Ravi P. Singh、Vinod K. Singh

  DOI：10.1016/j.tet.2006.09.005

  日期：2006.11

  A formal total synthesis of (+)-cardiobutanolide has been accomplished from D-glucose, a readily available precursor. (c) 2006 Elsevier Ltd. All rights reserved.
• Heteroannelated and 7-deoxygenated goniofufurone mimics with antitumour activity: Design, synthesis and preliminary SAR studies
  作者：Velimir Popsavin、Jovana Francuz、Bojana Srećo Zelenović、Goran Benedeković、Mirjana Popsavin、Vesna Kojić、Gordana Bogdanović

  DOI：10.1016/j.bmcl.2013.08.069

  日期：2013.10

  Cytotoxic (+)-goniofufurone mimic such as benzoxepane 2 was preferentially formed after the treatment of 7-O-benzoyl-5-O-benzyl (+)-goniofufurone derivative 6 with titanium(IV) fluoride. However, the corresponding 7-epimer 5 (derivative of 7-epi-goniofufurone) under the similar reaction conditions gave mainly 7-deoxy derivative 7 as a result of an unexpected 1,5-hydride shift. Extension of this methodology to the enantiomer ent-6 provided cytotoxic (-)-goniofufurone mimics ent-2 and ent-7. Synthesized compounds showed diverse growth inhibitory effects against selected tumour cell lines, but were devoid of any significant toxicity towards the normal foetal lung fibroblasts (MRC-5). A SAR study reveals the structural features of these lactones that are beneficial for their antiproliferative activity, such as presence of an additional oxepane ring, the absolute stereochemistry and the presence of a deoxy function at the C-7 position. (C) 2013 Elsevier Ltd. All rights reserved.