1-(3,4,6-tri-O-benzyl-α-D-glucopyranosyl)-3-(tetrahydropyran-2-yloxy)-1-propyne | 653569-52-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(3,4,6-tri-O-benzyl-α-D-glucopyranosyl)-3-(tetrahydropyran-2-yloxy)-1-propyne
• 英文别名: (2R,3S,4R,5R,6R)-2-[3-(oxan-2-yloxy)prop-1-ynyl]-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-ol
• CAS: 653569-52-9
• 化学式: C₃₅H₄₀O₇
• 分子量: 572.698
• InChiKey: AKGBMTLTWJOHCE-IUPFBVJPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  42
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  75.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-(3,4,6-tri-O-benzyl-α-D-glucopyranosyl)-3-(tetrahydropyran-2-yloxy)-1-propyne 在 吡啶 、 Dowex H⁽¹⁺⁾ resin 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 1-(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-glucopyranosyl)-1-propyn-3-ol
  参考文献：
  名称：

  From α‐1,2‐Anhydrosugars to C‐Glycosides: The Influence of Lewis Acids and Nucleophiles on the Stereochemistry

  摘要：

  Ring opening of the epoxide function in alpha-1,2-anhydrosugars with alkynyl zinc and titanium compounds proceeds with retention of configuration to afford alpha-C-alkynylglycosides in reasonable to good yields, while the use of the corresponding alkynyltrifluoroborates results in the formation alpha/beta mixtures. Vinyl nucleophiles predominantly afford alpha-products, whereas allyl and allenyl species almost exclusively yield beta-C-glycosides.

  DOI：

  10.1081/car-120026458
• 作为产物：
  描述：

  哌喃 、 3,4,6-tri-O-benzyl-D-glucal epoxide 在 正丁基锂 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.58h， 以72%的产率得到1-(3,4,6-tri-O-benzyl-α-D-glucopyranosyl)-3-(tetrahydropyran-2-yloxy)-1-propyne
  参考文献：
  名称：

  From α‐1,2‐Anhydrosugars to C‐Glycosides: The Influence of Lewis Acids and Nucleophiles on the Stereochemistry

  摘要：

  Ring opening of the epoxide function in alpha-1,2-anhydrosugars with alkynyl zinc and titanium compounds proceeds with retention of configuration to afford alpha-C-alkynylglycosides in reasonable to good yields, while the use of the corresponding alkynyltrifluoroborates results in the formation alpha/beta mixtures. Vinyl nucleophiles predominantly afford alpha-products, whereas allyl and allenyl species almost exclusively yield beta-C-glycosides.

  DOI：

  10.1081/car-120026458

文献信息

• From <i>α</i>‐1,2‐Anhydrosugars to <i>C</i>‐Glycosides: The Influence of Lewis Acids and Nucleophiles on the Stereochemistry
  作者：Michiel A. Leeuwenburgh、Gijsbert A. van der Marel、Herman S. Overkleeft、Jacques H. van Boom

  DOI：10.1081/car-120026458

  日期：2003.12.31

  Ring opening of the epoxide function in alpha-1,2-anhydrosugars with alkynyl zinc and titanium compounds proceeds with retention of configuration to afford alpha-C-alkynylglycosides in reasonable to good yields, while the use of the corresponding alkynyltrifluoroborates results in the formation alpha/beta mixtures. Vinyl nucleophiles predominantly afford alpha-products, whereas allyl and allenyl species almost exclusively yield beta-C-glycosides.