(3,4,6-tri-O-benzyl-α-D-glucopyranosyl)ethyne | 273925-95-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3,4,6-tri-O-benzyl-α-D-glucopyranosyl)ethyne
• 英文别名: (2R,3S,4R,5R,6R)-2-ethynyl-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-ol
• CAS: 273925-95-4
• 化学式: C₂₉H₃₀O₅
• 分子量: 458.554
• InChiKey: QAGMBOBUFLFFAO-XYPQWYOHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 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：

  (3,4,6-tri-O-benzyl-α-D-glucopyranosyl)ethyne 在 N-甲基吗啉 、 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 13.5h， 生成 ((2R,3aR,5R,6R,7S,7aS)-6,7-Bis-benzyloxy-5-benzyloxymethyl-3-methylene-hexahydro-furo[3,2-b]pyran-2-yl)-acetic acid ethyl ester
  参考文献：
  名称：

  Radical Cyclization of Sugar-Derived β-(Alkynyloxy)acrylates:  Synthesis of Novel Fused Ethers

  摘要：

  Tributyltin radical mediated cyclization of carbohydrate-derived beta-(alkynyloxy)acrylates leading to highly functionalized cis and trans-fused bicyclic ethers of various ring sizes is described. The efficacy of the radical cyclization is nicely illustrated in the iterative construction of a trans-fused tricyclic tetrahydropyran.

  DOI：

  10.1021/ol0000408
• 作为产物：
  描述：

  乙炔钠 、 3,4,6-tri-O-benzyl-D-glucal epoxide 在 zinc(II) chloride 作用下， 以 四氢呋喃 、 xylene 为溶剂， 反应 0.25h， 以84%的产率得到(3,4,6-tri-O-benzyl-α-D-glucopyranosyl)ethyne
  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

• Radical Cyclization of Sugar-Derived β-(Alkynyloxy)acrylates:  Synthesis of Novel Fused Ethers
  作者：Michiel A. Leeuwenburgh、Remy E. J. N. Litjens、Jeroen D. C. Codée、Herman S. Overkleeft、Gijsbert A. van der Marel、Jacques H. van Boom

  DOI：10.1021/ol0000408

  日期：2000.5.1

  Tributyltin radical mediated cyclization of carbohydrate-derived beta-(alkynyloxy)acrylates leading to highly functionalized cis and trans-fused bicyclic ethers of various ring sizes is described. The efficacy of the radical cyclization is nicely illustrated in the iterative construction of a trans-fused tricyclic tetrahydropyran.
• 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.