(3S,4S,5R)-3,4-dihydroxy-5-(prop-1-en-2-yl)dihydrofuran-2(3H)-one | 1448243-38-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (3S,4S,5R)-3,4-dihydroxy-5-(prop-1-en-2-yl)dihydrofuran-2(3H)-one
• 英文别名: (3S,4S,5R)-3,4-dihydroxy-5-prop-1-en-2-yloxolan-2-one
• CAS: 1448243-38-6
• 化学式: C₇H₁₀O₄
• 分子量: 158.154
• InChiKey: VSYDYJGRMFSSJQ-HCWXCVPCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3S,4S,5R)-3,4-dihydroxy-5-(prop-1-en-2-yl)dihydrofuran-2(3H)-one 、 三异丙基硅基三氟甲磺酸酯 在 2,6-二甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以79%的产率得到(3S,4R,5R)-5-(prop-1-en-2-yl)-3,4-bis((triisopropylsilyl)oxy)dihydrofuran-2(3H)-one
  参考文献：
  名称：

  A C2-Symmetric Pool Based Synthesis of the Furanoside of Hygromycin A

  摘要：

  The readily available and inexpensive D-tartaric acid serves as the chiral building block for synthesis of the furanoside of hygromycin A. Key to our successes in the asymmetric synthesis of the furanose segment was the melding of several key reactions, such as the successful application of the monosilylation of C-2-symmetric diol, diastereocontrolled di(2-propenyl)zinc addition to the aldehyde, and TMSCl-MeOH promoted desilylation, acetal-cleavage, and intramolecular esterification in one-step.

  DOI：

  10.3987/com-12-s(n)19
• 作为产物：
  描述：

  (4S,5S)-5-((R)-1-(tert-butyldimethylsilyloxy)-2-methylallyl)-2,2-dimethyl-1,3-dioxolane-4-carboxylic acid 在 甲醇 、 三甲基氯硅烷 作用下， 反应 3.0h， 以89%的产率得到(3S,4S,5R)-3,4-dihydroxy-5-(prop-1-en-2-yl)dihydrofuran-2(3H)-one
  参考文献：
  名称：

  A C2-Symmetric Pool Based Synthesis of the Furanoside of Hygromycin A

  摘要：

  The readily available and inexpensive D-tartaric acid serves as the chiral building block for synthesis of the furanoside of hygromycin A. Key to our successes in the asymmetric synthesis of the furanose segment was the melding of several key reactions, such as the successful application of the monosilylation of C-2-symmetric diol, diastereocontrolled di(2-propenyl)zinc addition to the aldehyde, and TMSCl-MeOH promoted desilylation, acetal-cleavage, and intramolecular esterification in one-step.

  DOI：

  10.3987/com-12-s(n)19

文献信息

• A C2-Symmetric Pool Based Synthesis of the Furanoside of Hygromycin A
  作者：Tu-Hsin Yan、Hong-Jay Lo、Yuan-Kang Chang

  DOI：10.3987/com-12-s(n)19

  日期：——

  The readily available and inexpensive D-tartaric acid serves as the chiral building block for synthesis of the furanoside of hygromycin A. Key to our successes in the asymmetric synthesis of the furanose segment was the melding of several key reactions, such as the successful application of the monosilylation of C-2-symmetric diol, diastereocontrolled di(2-propenyl)zinc addition to the aldehyde, and TMSCl-MeOH promoted desilylation, acetal-cleavage, and intramolecular esterification in one-step.