(8aR,9R,10S,11R,12aS,Z)-9,10-bis(benzyloxy)-11-(benzyloxymethyl)-8a,9,10,11-tetrahydro-2H-pyrano[2,3-b][1,6]dioxecin-7(5H,8H,12aH)one | 1124226-20-5

• 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: (8aR,9R,10S,11R,12aS,Z)-9,10-bis(benzyloxy)-11-(benzyloxymethyl)-8a,9,10,11-tetrahydro-2H-pyrano[2,3-b][1,6]dioxecin-7(5H,8H,12aH)one
• CAS: 1124226-20-5
• 化学式: C₃₃H₃₆O₇
• 分子量: 544.645
• InChiKey: DWLASMAXGQDMMO-ZWJWPSTRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.23
• 重原子数：
  40.0
• 可旋转键数：
  10.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  72.45
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  allyl 3,4,6-tri-O-benzyl-2-deoxy-2-[(allyloxycarbonyl)methyl]-α-D-glucopyranoside 在 Grubbs catalyst first generation 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以75%的产率得到(8aR,9R,10S,11R,12aS,Z)-9,10-bis(benzyloxy)-11-(benzyloxymethyl)-8a,9,10,11-tetrahydro-2H-pyrano[2,3-b][1,6]dioxecin-7(5H,8H,12aH)one
  参考文献：
  名称：

  Stereoselective diversity-oriented syntheses of functionalized saccharides from bicyclic carbohydrate 1,2-lactones

  摘要：

  Bicyclic carbohydrate 1,2-lactones have been synthesized in only two steps and high yields by saponification and subsequent cyclization from known malonate addition products to glycals. The gluco-configured lactone serves as an important precursor for diversity-oriented syntheses. Thus, stereoselective opening of the lactone ring was realized with various nucleophiles in the presence of Sc(OTf)(3). This enabled the introduction of different substituents at the anomeric position, to afford a broad variety of 1-functionalized carbohydrates. On the other hand, stereoselective alpha-substitution of the gluco-configured lactone with different electrophiles and subsequent ring opening gives a collection of 2-functionalized saccharides. More than 30 products have been isolated in analytically pure form, and their configurations were unequivocally established by various NMR methods. Thus, carbohydrate 1,2-lactones are attractive precursors for the stereoselective synthesis of diverse saccharides. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.01.069