2,2,2-Trichloro-acetimidic acid (1R,2S,4R,5S,6R)-2-allyloxy-4-methyl-3,7-dioxa-bicyclo[4.1.0]hept-5-yl ester | 1021496-24-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,2,2-Trichloro-acetimidic acid (1R,2S,4R,5S,6R)-2-allyloxy-4-methyl-3,7-dioxa-bicyclo[4.1.0]hept-5-yl ester
• 英文别名: [(1R,2S,4R,5S,6R)-4-methyl-2-prop-2-enoxy-3,7-dioxabicyclo[4.1.0]heptan-5-yl] 2,2,2-trichloroethanimidate
• CAS: 1021496-24-1
• 化学式: C₁₁H₁₄Cl₃NO₄
• 分子量: 330.595
• InChiKey: INTPTEKZFRXTKP-WUNNTHRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  64.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,2,2-Trichloro-acetimidic acid (1R,2S,4R,5S,6R)-2-allyloxy-4-methyl-3,7-dioxa-bicyclo[4.1.0]hept-5-yl ester 在 盐酸 、 三氟甲磺酸三甲基硅酯 、 silica gel 、 sodium hydride 、 palladium dichloride 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 生成 Acetic acid (2R,3R,4S,5R)-4-acetylamino-5-benzyloxy-6-((3aS,4S,6R,7R,7aS)-4-methoxy-2,2,6-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yloxy)-2-methyl-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  First preparative synthesis of a 3-acetamido-3,6-dideoxy-d-galactopyranose glycosyl donor via intramolecular cyclization of an epoxytrichloroacetimidate

  摘要：

  The preparative synthesis of a 3 -acetamido- 3,6-dideoxy -D-galactopyranose N-phenyl-trifluoroacetimidate donor has been accomplished using as key step a silica gel mediated cyclization of an epoxytrichloroacetimidate, while other more conventional routes to aminosugars failed. Test glycosylations with the N-phenyl-trifluoroacetimidate donor are also reported. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.04.065
• 作为产物：
  描述：

  allyl α-D-isopropylidene-α-D-fucopyranoside 在 camphor-10-sulfonic acid 、 sodium methylate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.67h， 生成 2,2,2-Trichloro-acetimidic acid (1R,2S,4R,5S,6R)-2-allyloxy-4-methyl-3,7-dioxa-bicyclo[4.1.0]hept-5-yl ester
  参考文献：
  名称：

  First preparative synthesis of a 3-acetamido-3,6-dideoxy-d-galactopyranose glycosyl donor via intramolecular cyclization of an epoxytrichloroacetimidate

  摘要：

  The preparative synthesis of a 3 -acetamido- 3,6-dideoxy -D-galactopyranose N-phenyl-trifluoroacetimidate donor has been accomplished using as key step a silica gel mediated cyclization of an epoxytrichloroacetimidate, while other more conventional routes to aminosugars failed. Test glycosylations with the N-phenyl-trifluoroacetimidate donor are also reported. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.04.065

文献信息

• First preparative synthesis of a 3-acetamido-3,6-dideoxy-d-galactopyranose glycosyl donor via intramolecular cyclization of an epoxytrichloroacetimidate
  作者：Emiliano Bedini、Alfonso Iadonisi、Antonella Carabellese、Michelangelo Parrilli

  DOI：10.1016/j.tetlet.2004.04.065

  日期：2004.5

  The preparative synthesis of a 3 -acetamido- 3,6-dideoxy -D-galactopyranose N-phenyl-trifluoroacetimidate donor has been accomplished using as key step a silica gel mediated cyclization of an epoxytrichloroacetimidate, while other more conventional routes to aminosugars failed. Test glycosylations with the N-phenyl-trifluoroacetimidate donor are also reported. (C) 2004 Elsevier Ltd. All rights reserved.