azane;[(2R,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-[[(1S,2R,6R,8R,9S)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-8-yl]methoxy]oxan-3-yl]sulfamic acid | 1013643-46-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: azane;[(2R,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-[[(1S,2R,6R,8R,9S)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-8-yl]methoxy]oxan-3-yl]sulfamic acid
• CAS: 1013643-46-3
• 化学式: C₁₈H₃₀NO₁₃S*H₄N
• 分子量: 518.54
• InChiKey: ZPIGNDJBLAXJBR-NKMDSQKJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.37
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  201
• 氢给体数：
  6
• 氢受体数：
  15

反应信息

• 作为产物：
  描述：

  2,2,2-trichloroethyl N-[(2R,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-[[(1S,2R,6R,8R,9S)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-8-yl]methoxy]oxan-3-yl]sulfamate 在 氯化铵 、 锌 作用下， 以 甲醇 为溶剂， 以92%的产率得到azane;[(2R,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-[[(1S,2R,6R,8R,9S)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-8-yl]methoxy]oxan-3-yl]sulfamic acid
  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