trans-caffeoyl-6-O-D-glucono-γ-lactone | 864512-90-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: trans-caffeoyl-6-O-D-glucono-γ-lactone
• 英文别名: vittarilide A；vittarilide-A；[(2R)-2-[(2R,3R,4R)-3,4-dihydroxy-5-oxooxolan-2-yl]-2-hydroxyethyl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• CAS: 864512-90-3
• 化学式: C₁₅H₁₆O₉
• 分子量: 340.287
• InChiKey: VFAMSKXGISQMEE-LSZAEMBDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  154
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  TRANS-咖啡酸 在 咪唑 、 4-二甲氨基吡啶 、 三氟化硼乙醚 、 水 、 potassium carbonate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 11.33h， 生成 trans-caffeoyl-6-O-D-glucono-γ-lactone
  参考文献：
  名称：

  First total synthesis and absolute stereochemical assignment of vittarilide-A, an antioxidant extractive component isolated from Vittaria anguste-elongata Hayata

  摘要：

  The first stereocontrolled synthesis of vittarilide-A and its C5-epimer was completed from D-glucuronolactone. Comparison with the spectroscopic properties reported for authentic material has given a clear indication as to the absolute stereochemistry of the natural vittarilide-A. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.06.105

文献信息

• Concise stereoselective synthesis of vittarilide-A
  作者：Rajashekar Reddy Nimmareddy、Himabindu Gandham、Shivanagababu Challa、Janardana Reddi Desireddi、Narender Reddy Modugu、Krishnakanth Reddy Leleti

  DOI：10.1016/j.tet.2024.134013

  日期：2024.6

  A concise and stereoselective synthesis of vittarilide-A, an antioxidant isolated from Hayata, was accomplished in 4 linear synthetic steps with an overall yield of 17.0 % from naturally available D-glucono-1,5-lactone. The key reactions employed were tetra--(-butyldimethylsilyl)-D-glucono-1,4-lactone formed by silylation of D-glucono-1,5-lactone, selective TBDMS deprotection followed by Yamaguchi

  通过 4 个线性合成步骤完成了 vittarilide-A（一种从 Hayata 中分离出来的抗氧化剂）的简洁立体选择性合成，天然 D-葡萄糖酸-1,5-内酯的总产率为 17.0%。所采用的关键反应是通过 D-葡萄糖酸-1,5-内酯的甲硅烷基化形成四-(丁基二甲基甲硅烷基)-D-葡萄糖酸-1,4-内酯，选择性 TBDMS 脱保护，然后进行 Yamaguchi 酯化。
• Stereoselective synthesis of vittarilide-A
  作者：Jhillu Singh Yadav、Vijaya Vardhan Chinnam、Bendapudi Bala Murali Krishna、Kundeti Lakshmi Srinivasa Rao、Saibal Das

  DOI：10.1016/j.tetlet.2015.02.028

  日期：2015.3

  A facile and stereoselective synthesis of vittarilide-A, having promising antioxidant property was accomplished in 12 linear synthetic steps with an overall yield of 6.34% using a chiral pool approach from naturally available diethyl tartrate. The key reactions employed were diastereoselective vinylation, Sharpless asymmetric dihydroxylation, (2,2,6,6-tetramethylpiperidin-1-yl)oxy radical (TEMPO), bis(acetoxy)iodo-benzene (BAIR) mediated tandem oxidation followed by lactonization and finally esterification under Yamaguchi conditions. (C) 2015 Elsevier Ltd. All rights reserved.