isopropyl 3,4,6-tri-O-benzyl-2-deoxy-2-[(isopropoxycarbonyl)methyl]-α-D-glucopyranoside | 1124225-85-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: isopropyl 3,4,6-tri-O-benzyl-2-deoxy-2-[(isopropoxycarbonyl)methyl]-α-D-glucopyranoside
• 英文别名: propan-2-yl 2-[(2S,3R,4R,5S,6R)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-2-propan-2-yloxyoxan-3-yl]acetate
• CAS: 1124225-85-9
• 化学式: C₃₅H₄₄O₇
• 分子量: 576.73
• InChiKey: KNLQDUNPIPIVBO-VLCQNZNESA-N

物化性质

• 沸点：
  646.3±55.0 °C(predicted)
• 密度：
  1.14±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  42
• 可旋转键数：
  16
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  methyl 3,4,6-tri-O-benzyl-2-deoxy-2-C-[(bis-methoxycarbonyl)methyl]-β-D-glucopyranoside 在 calcium sulfate 、 lithium hydroxide monohydrate 、 溶剂黄146 、 scandium tris(trifluoromethanesulfonate) 作用下， 以 甲醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 2.5h， 生成 isopropyl 3,4,6-tri-O-benzyl-2-deoxy-2-[(isopropoxycarbonyl)methyl]-β-D-glucopyranoside 、 isopropyl 3,4,6-tri-O-benzyl-2-deoxy-2-[(isopropoxycarbonyl)methyl]-α-D-glucopyranoside
  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

文献信息

• Convenient Synthesis of Bicyclic Carbohydrate 1,2-Lactones and Their Stereoselective Opening to 1-Functionalized Glucose Derivatives
  作者：Jian Yin、Torsten Linker

  DOI：10.1002/chem.200802178

  日期：2009.1

  C‐2 branched carbohydrates 1 cyclize under conditions of decarboxylation to the hitherto unknown carbohydrate 1,2‐lactones 2 in high yields. The gluco isomer can be opened at the anomeric position with various nuceophiles in the presence of Sc(OTf)3, which allows the stereoselective synthesis of 1‐functionalized glucose derivatives 3. Thus, 1,2‐bis‐C‐branched saccharides become available in only a few

  关闭并重新营业：C-2分支碳水化合物1在脱羧条件下以高收率环化为迄今未知的碳水化合物1,2-内酯2。的葡糖异构体可以在异头位置与各种nuceophiles在钪（OTF）的存在下被打开3，这允许1官能化的葡萄糖衍生物的立体选择性合成3。因此，从糖基开始仅需几个步骤即可获得1,2 -bis-C支链糖。