2,3,6-tri-O-pivaloyl-α-D-glucopyranosyl trichloroacetimidate | 144102-46-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,6-tri-O-pivaloyl-α-D-glucopyranosyl trichloroacetimidate
• 英文别名: pivaloyl(-2)[pivaloyl(-3)][pivaloyl(-6)]Glc(a)-O-C(NH)CCl3；[(2R,3R,4S,5R,6R)-4,5-bis(2,2-dimethylpropanoyloxy)-3-hydroxy-6-(2,2,2-trichloroethanimidoyl)oxyoxan-2-yl]methyl 2,2-dimethylpropanoate
• CAS: 144102-46-5
• 化学式: C₂₃H₃₆Cl₃NO₉
• 分子量: 576.899
• InChiKey: RRDWTMGUDNEPFU-UXXRCYHCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  36
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  141
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2,3,6-tri-O-pivaloyl-α-D-glucopyranosyl trichloroacetimidate 在 甲醇 、 sodium methylate 作用下， 生成 testosterone-β-D-glucopyranoside
  参考文献：
  名称：

  A novel synthesis of protected glucose intermediates.

  摘要：

  The 1,2,4,6-Tetra-O-pivaloyl-D-gluco-pyranose 3 and 1,2,3,6-Tetra-O-pivaloyl-D-glucopyranose 4 have been prepared in one step from anhydrous glucose and pivaloyl chloride. These new intermediates can be converted into the corresponding esters, or used in the synthesis of a disaccharide in good yield. Thus, 2,3,6-Tri-O-pivaloyl-gluco-pyranose 10 can be prepared from 4, and used for preparation of beta-gluco derivatives via the corresponding trichloroacetimidate 12.

  DOI：

  10.1016/s0040-4039(00)61283-2
• 作为产物：
  描述：

  1,2,3,6-tetra-O-pivaloyl-β-D-glucopyranose 在 乙酸肼 、 caesium carbonate 作用下， 生成 2,3,6-tri-O-pivaloyl-α-D-glucopyranosyl trichloroacetimidate
  参考文献：
  名称：

  A novel synthesis of protected glucose intermediates.

  摘要：

  The 1,2,4,6-Tetra-O-pivaloyl-D-gluco-pyranose 3 and 1,2,3,6-Tetra-O-pivaloyl-D-glucopyranose 4 have been prepared in one step from anhydrous glucose and pivaloyl chloride. These new intermediates can be converted into the corresponding esters, or used in the synthesis of a disaccharide in good yield. Thus, 2,3,6-Tri-O-pivaloyl-gluco-pyranose 10 can be prepared from 4, and used for preparation of beta-gluco derivatives via the corresponding trichloroacetimidate 12.

  DOI：

  10.1016/s0040-4039(00)61283-2

文献信息

• Synthesis and utilization of saccharide intermediates
  作者：D. Becker、N. Galili

  DOI：10.1016/0008-6215(93)84121-l

  日期：1993.10

  A new method has been developed for preparation of partially pivaloylated saccharides in one step from readily available starting materials. These intermediates were used in the synthesis of disaccharides and a glucosteroid.
• A novel synthesis of protected glucose intermediates.
  作者：D. Becker、N. Galili

  DOI：10.1016/s0040-4039(00)61283-2

  日期：1992.8

  The 1,2,4,6-Tetra-O-pivaloyl-D-gluco-pyranose 3 and 1,2,3,6-Tetra-O-pivaloyl-D-glucopyranose 4 have been prepared in one step from anhydrous glucose and pivaloyl chloride. These new intermediates can be converted into the corresponding esters, or used in the synthesis of a disaccharide in good yield. Thus, 2,3,6-Tri-O-pivaloyl-gluco-pyranose 10 can be prepared from 4, and used for preparation of beta-gluco derivatives via the corresponding trichloroacetimidate 12.