allyl 3,5-O-(1-methylethylidene)-α and β-D-xylofuranoside | 916153-97-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 3,5-O-(1-methylethylidene)-α and β-D-xylofuranoside
• 英文别名: (4aR,7R,7aR)-2,2-dimethyl-6-prop-2-enoxy-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3]dioxin-7-ol
• CAS: 916153-97-4
• 化学式: C₁₁H₁₈O₅
• 分子量: 230.261
• InChiKey: LVXOMAJMKNTUBJ-HNJRMYHASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  allyl 3,5-O-(1-methylethylidene)-α and β-D-xylofuranoside 在 咪唑 、 正丁基锂 、 potassium tert-butylate 、 碘 、 sodium hydride 、 对甲苯磺酸 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 31.75h， 生成 (2S,3R,4S)-1-iodo-2-methoxy-4-phenylmethoxyhex-5-en-3-ol
  参考文献：
  名称：

  孢子内酯B的第一个全合成

  摘要：

  描述了天然细胞毒剂孢子内酯B的第一个全合成。d-木糖用作手性模板，以在合成过程中预先控制绝对构型。山口酯化和闭环复分解极大地促进了目标化合物的完成。

  DOI：

  10.1016/j.tetlet.2006.09.145
• 作为产物：
  描述：

  allyl α,β-D-xylofuranoside 、 丙酮 在 copper(II) sulfate 作用下， 生成 allyl 3,5-O-(1-methylethylidene)-α and β-D-xylofuranoside
  参考文献：
  名称：

  Synthesis of congeners of migrastatin and dorrigocin A from d-xylose

  摘要：

  Migrastatin and dorrigocin A analogues have potential as anti-metastatic agents that act by targeting the actin-bundling protein, fascin. Syntheses of close structural analogues of these agents have been achieved. Wittig and Ando olefination reactions with an aldehyde obtained from D-xylose, respectively, gave two trisubstituted alkene intermediates that were then elaborated into either macrolactone or macrolactam analogues of migrastatin or to an acyclic dorrigocin A analogue. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.07.141

文献信息

• Convergent synthesis of polyether ionophore antibiotics: the synthesis of the monensin bis(tetrahydrofuran) via the Claisen rearrangement of an ester enolate with a .beta.-leaving group
  作者：Robert E. Ireland、Daniel W. Norbeck

  DOI：10.1021/ja00297a038

  日期：1985.5
• Gopishetty, Bhaskar; Zhu, Jinge; Rajan, Rakhi, Journal of the American Chemical Society, 2009, vol. 131, p. 1243 - 1250
  作者：Gopishetty, Bhaskar、Zhu, Jinge、Rajan, Rakhi、Sobczak, Adam J.、Wnuk, Stanislaw F.、et al.

  DOI：——

  日期：——
• The First Total Synthesis of Sporiolide A
  作者：Yuguo Du、Qi Chen、Robert J. Linhardt

  DOI：10.1021/jo0615504

  日期：2006.10.1

  The first total synthesis of the natural cytotoxic agent sporiolide A has been accomplished from D-glucal in 16 steps with 6.1% overall yield. Carbohydrates were applied as the chiral templates to manipulate the absolute configuration during the synthesis. Pyridinium chlorochromate (PCC)-promoted transformation of the cyclic enol-ether to lactone, followed by Yamaguchi esterification and intramolecular ring closure metathesis, greatly facilitates synthesis of the target compound.
• Synthesis of congeners of migrastatin and dorrigocin A from d-xylose
  作者：Ying Zhou、Paul V. Murphy

  DOI：10.1016/j.tetlet.2010.07.141

  日期：2010.10

  Migrastatin and dorrigocin A analogues have potential as anti-metastatic agents that act by targeting the actin-bundling protein, fascin. Syntheses of close structural analogues of these agents have been achieved. Wittig and Ando olefination reactions with an aldehyde obtained from D-xylose, respectively, gave two trisubstituted alkene intermediates that were then elaborated into either macrolactone or macrolactam analogues of migrastatin or to an acyclic dorrigocin A analogue. (C) 2010 Elsevier Ltd. All rights reserved.
• The first total synthesis of sporiolide B
  作者：Qi Chen、Yuguo Du

  DOI：10.1016/j.tetlet.2006.09.145

  日期：2006.11

  The first total synthesis of natural cytotoxic agent, sporiolide B, is described. d-Xylose was used as the chiral template to pre-control the absolute configuration during the synthesis. Yamaguchi esterification and ring closing metathesis greatly facilitate the target compound accomplishment.

  描述了天然细胞毒剂孢子内酯B的第一个全合成。d-木糖用作手性模板，以在合成过程中预先控制绝对构型。山口酯化和闭环复分解极大地促进了目标化合物的完成。