[(2S,3aR,5R,6R,7S,7aR)-6,7-dibenzoyloxy-2-phenyl-2-prop-2-ynoxy-5,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-b]pyran-5-yl]methyl benzoate | 953795-81-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [(2S,3aR,5R,6R,7S,7aR)-6,7-dibenzoyloxy-2-phenyl-2-prop-2-ynoxy-5,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-b]pyran-5-yl]methyl benzoate
• CAS: 953795-81-8
• 化学式: C₃₇H₃₀O₁₀
• 分子量: 634.639
• InChiKey: JWQDPFKSUXOIFO-NUDBXABSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  47
• 可旋转键数：
  13
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  116
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  [(2S,3aR,5R,6R,7S,7aR)-6,7-dibenzoyloxy-2-phenyl-2-prop-2-ynoxy-5,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-b]pyran-5-yl]methyl benzoate 、 胆固醇 在 gold(III) bromide 、 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以60%的产率得到cholesteryl 2,3,4,6-tetra-O-benzoyl β-D-glucopyranoside
  参考文献：
  名称：

  Propargyl 1,2-orthoesters as glycosyl donors: stereoselective synthesis of 1,2-trans glycosides and disaccharides

  摘要：

  Propargyl 1,2-orthoesters are identified as glycosyl donors. Various glycosides and disaccharides were synthesized in a stereoselective manner using AuBr3 as the promoter. AuBr3 may activate the alkyne resulting in the formation of a 1,2-dioxolenium ion and also behaves as a Lewis acid to facilitate the attack of the glycosyl acceptor. The versatility of the protocol was demonstrated using a panel of aglycones comprising aliphatic, alicyclic, steroidal and sugar alcohols. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.07.015
• 作为产物：
  描述：

  2,3,4,6-tetra-O-benzoylglucosyl bromide 、 2-丙炔-1-醇 在 2,6-二甲基吡啶 、 四丁基碘化铵 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以85%的产率得到[(2S,3aR,5R,6R,7S,7aR)-6,7-dibenzoyloxy-2-phenyl-2-prop-2-ynoxy-5,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-b]pyran-5-yl]methyl benzoate
  参考文献：
  名称：

  Propargyl 1,2-orthoesters as glycosyl donors: stereoselective synthesis of 1,2-trans glycosides and disaccharides

  摘要：

  Propargyl 1,2-orthoesters are identified as glycosyl donors. Various glycosides and disaccharides were synthesized in a stereoselective manner using AuBr3 as the promoter. AuBr3 may activate the alkyne resulting in the formation of a 1,2-dioxolenium ion and also behaves as a Lewis acid to facilitate the attack of the glycosyl acceptor. The versatility of the protocol was demonstrated using a panel of aglycones comprising aliphatic, alicyclic, steroidal and sugar alcohols. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.07.015

文献信息

• Propargyl 1,2-orthoesters as glycosyl donors: stereoselective synthesis of 1,2-trans glycosides and disaccharides
  作者：Gopalsamy Sureshkumar、Srinivas Hotha

  DOI：10.1016/j.tetlet.2007.07.015

  日期：2007.9

  Propargyl 1,2-orthoesters are identified as glycosyl donors. Various glycosides and disaccharides were synthesized in a stereoselective manner using AuBr3 as the promoter. AuBr3 may activate the alkyne resulting in the formation of a 1,2-dioxolenium ion and also behaves as a Lewis acid to facilitate the attack of the glycosyl acceptor. The versatility of the protocol was demonstrated using a panel of aglycones comprising aliphatic, alicyclic, steroidal and sugar alcohols. (C) 2007 Elsevier Ltd. All rights reserved.