3,4,6-tri-O-acetyl-2-deoxy-2-trifluoroacetamido-α-D-glucopyranosyl chloride | 136053-15-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3,4,6-tri-O-acetyl-2-deoxy-2-trifluoroacetamido-α-D-glucopyranosyl chloride
• 英文别名: 3,4,6-tri-O-acetyl-2-trifluoroacetamido-2-deoxy-α-D-glucopyranosyl chloride
• CAS: 136053-15-1
• 化学式: C₁₄H₁₇ClF₃NO₈
• 分子量: 419.739
• InChiKey: UEKYDYYCHNPZAC-OOCWMUITSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.42
• 重原子数：
  27.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  117.23
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  3,4,6-tri-O-acetyl-2-deoxy-2-trifluoroacetamido-α-D-glucopyranosyl chloride 在 水 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 2-chloroethyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of defined mono-de-N-acetylated β-(1→6)-N-acetyl-d-glucosamine oligosaccharides to characterize PgaB hydrolase activity

  摘要：

  使用汇合合成法得到了单乙酰化的β-(1→6)-N-乙酰-D-葡萄糖胺五糖和七糖。去乙酰化的位置决定了PgaB水解的选择性。

  DOI：

  10.1039/c9ob02079a
• 作为产物：
  描述：

  1,3,4,6-四-O-乙酰基-2-氨基-2-脱氧-Β-D-葡萄糖盐酸盐 在 吡啶 、 1,1-二氯甲醚 、 zinc(II) chloride 作用下， 以 氯仿 为溶剂， 反应 1.0h， 生成 3,4,6-tri-O-acetyl-2-deoxy-2-trifluoroacetamido-α-D-glucopyranosyl chloride
  参考文献：
  名称：

  Differently N-protected 3,4,6-tri-O-acetyl-2-amino-2-deoxy-d-glucopyranosyl chlorides and their application in the synthesis of diosgenyl 2-amino-2-deoxy-β-d-glucopyranoside

  摘要：

  Four differently N-protected 3,4,6-tri-O-acetyl-2-amino-2-deoxy-D-glucopyranosyl chlorides were synthesized and used as glycosyl donors in reactions with diosgenin. The following amine group protections were tested: trifluoroacetyl (TFA), 2,2,2-trichloroethoxycarbonyl (Troc), phthaloyl (Phth), and tetrachlorophthaloyl (TCP). Products of glycosylation were deprotected to yield diosgenyl 2-amino-2-deoxy-beta-D-glucopyranoside. The efficiency of the procedures is discussed. Additionally, a single-crystal X-ray diffraction analysis for 3,4,6-tri-O-acetyl-2-deoxy-2-tetrachlorophthalimido-beta-D-glucopyranosyl chloride is reported. Orientations of the pyranose substituents as well as the planarity of the acetoxy and phthalimide groups in the crystal lattice are discussed. Structural evidence is presented for a mesomeric effect in both groups. The preference of the cis over trans orientation of the acetoxy group is confirmed in the crystal lattice. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2012.11.020

文献信息

• Chemoselective Synthesis of Oligosaccharides of 2-Deoxy-2-aminosugars
  作者：Aileen F. G. Bongat、Medha N. Kamat、Alexei V. Demchenko

  DOI：10.1021/jo062171d

  日期：2007.2.1

  Along with the application of the S-benzoxazolyl glycosides to the high-yielding synthesis of disaccharides of the 2-amino-2-deoxy series, chemoselective assembly of oligosaccharides containing multiple residues of 2-amino-2-deoxyglycoses is reported. This modified armed-disarmed approach is relying on the observation that 2-N-trichloroethoxycarbonyl derivatives of S-benzoxazolyl glycosides are significantly more reactive than their 2-N-phthaloyl counterparts in MeOTf-promoted glycosylations. This allowed efficient chemoselective synthesis of 1,2-trans-linked oligosaccharides, the disarmed reducing end of which can be activated for immediate second step glycosidation in the presence of a more powerful activator, AgOTf. As a result of this two-step activation, trans-trans-patterned trisaccharides could be assembled in a highly efficient manner. This result differs from the classic armed-disarmed technique, according to which usually cis-trans-patterned oligosaccharides are generated.