3,4,6-tri-O-acetyl-N-trichloroethylsulfuryl-α-D-glucosaminosyl trichloroacetimidate | 1013643-34-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4,6-tri-O-acetyl-N-trichloroethylsulfuryl-α-D-glucosaminosyl trichloroacetimidate
• 英文别名: [(2R,3S,4R,5R,6R)-3,4-diacetyloxy-6-(2,2,2-trichloroethanimidoyl)oxy-5-(2,2,2-trichloroethoxysulfonylamino)oxan-2-yl]methyl acetate
• CAS: 1013643-34-9
• 化学式: C₁₆H₂₀Cl₆N₂O₁₁S
• 分子量: 661.126
• InChiKey: MSICHKODBMOZFD-SYLRKERUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  36
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  185
• 氢给体数：
  2
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 、 3,4,6-tri-O-acetyl-N-trichloroethylsulfuryl-α-D-glucosaminosyl trichloroacetimidate 在 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 以82%的产率得到
  参考文献：
  名称：

  Effective protection of the N-sulfate of glucosamine derivatives with the 2,2,2-trichloroethyl group

  摘要：

  The 2,2,2-trichloroethyl (TCE) group was utilized as the first protecting group for N-sulfates (chlorosulfuric acid TCE ester, Et3N, DMAP, DMF). Glycosylation with 3,4,6-tri-O-acetyl-N-trichloroethylsulfuryl-alpha-D-glucosaminosyl trichloroacetimidate provided the corresponding beta-glucosaminosides stereoselectively and in excellent yields. The TCE protection stayed stable under a variety of conditions for the manipulation of other protecting groups, and was readily removable with zinc in the presence of ammonium chloride in methanol. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.12.132
• 作为产物：
  描述：

  [(2R,3S,4R,5R,6S)-3,4-diacetyloxy-6-hydroxy-5-(2,2,2-trichloroethoxysulfonylamino)oxan-2-yl]methyl acetate 、 三氯乙腈 在 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 10.0h， 以88%的产率得到3,4,6-tri-O-acetyl-N-trichloroethylsulfuryl-α-D-glucosaminosyl trichloroacetimidate
  参考文献：
  名称：

  Effective protection of the N-sulfate of glucosamine derivatives with the 2,2,2-trichloroethyl group

  摘要：

  The 2,2,2-trichloroethyl (TCE) group was utilized as the first protecting group for N-sulfates (chlorosulfuric acid TCE ester, Et3N, DMAP, DMF). Glycosylation with 3,4,6-tri-O-acetyl-N-trichloroethylsulfuryl-alpha-D-glucosaminosyl trichloroacetimidate provided the corresponding beta-glucosaminosides stereoselectively and in excellent yields. The TCE protection stayed stable under a variety of conditions for the manipulation of other protecting groups, and was readily removable with zinc in the presence of ammonium chloride in methanol. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.12.132