2-amino-3,4,6-tri-O-benzyl-2-deoxy-1-O-2-N-(phenylmethan-yl-ylidene)-α-D-glucopyranose | 459146-96-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-amino-3,4,6-tri-O-benzyl-2-deoxy-1-O-2-N-(phenylmethan-yl-ylidene)-α-D-glucopyranose
• CAS: 459146-96-4
• 化学式: C₃₄H₃₃NO₅
• 分子量: 535.64
• InChiKey: GRBRDOAAADYROX-CQYMVYICSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.94
• 重原子数：
  40.0
• 可旋转键数：
  11.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  58.51
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2-amino-3,4,6-tri-O-benzyl-2-deoxy-1-O-2-N-(phenylmethan-yl-ylidene)-α-D-glucopyranose 在 盐酸 、 水 作用下， 以 四氢呋喃 为溶剂， 以38%的产率得到2-benzamido-3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranose
  参考文献：
  名称：

  The preparation of 2-iodoamides from glucals and their further transformations into oxazolines

  摘要：

  2-Deoxy-2-iodo-glycosylamides have been prepared from a variety of protected D-glucals by their reaction with N-iodo-succinimide and amides. Benzyl protected 2-iodoamides, when treated with sodium hydride and 15-crown-5, gave stable C1 N-linked 2-glycooxazolines as the major products. Silyl protected 2-iodoamides afforded the C1 C-linked 2-glycooxazolines; presumably by the rearrangement of unstable N-acylaziridine intermediates. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.06.082
• 作为产物：
  描述：

  3,4,6-三苄氧基-D-葡萄烯糖 、 苯甲酰胺 在 N-碘代丁二酰亚胺 、 sodium hydride 作用下， 以 二氯甲烷 为溶剂， 反应 80.0h， 生成 2-amino-3,4,6-tri-O-benzyl-2-deoxy-1-O-2-N-(phenylmethan-yl-ylidene)-α-D-glucopyranose
  参考文献：
  名称：

  The preparation of 2-iodoamides from glucals and their further transformations into oxazolines

  摘要：

  2-Deoxy-2-iodo-glycosylamides have been prepared from a variety of protected D-glucals by their reaction with N-iodo-succinimide and amides. Benzyl protected 2-iodoamides, when treated with sodium hydride and 15-crown-5, gave stable C1 N-linked 2-glycooxazolines as the major products. Silyl protected 2-iodoamides afforded the C1 C-linked 2-glycooxazolines; presumably by the rearrangement of unstable N-acylaziridine intermediates. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.06.082

文献信息

• <i>C2</i>-Amidoglycosylation. Scope and Mechanism of Nitrogen Transfer
  作者：Jing Liu、David Y. Gin

  DOI：10.1021/ja026281n

  日期：2002.8.1

  A one-pot C2-amidoglycosylation reaction for the synthesis of 2-N-acyl-2-deoxy-beta-pyranosides from glycals is described. Glycal donors activated by the reagent combination of thianthrene-5-oxide (11) and Tf2O, followed by treatment with an amide nucleophile and a glycosyl acceptor, lead to the formation of various C2-amidoglycoconjugates. Both the C2-nitrogen transfer and the glycosidic bond formation

  描述了用于从糖基合成 2-N-酰基-2-脱氧-β-吡喃糖苷的一锅 C2-酰胺糖基化反应。由 thanthrene-5-oxide (11) 和 Tf2O 的试剂组合激活的糖基供体，然后用酰胺亲核试剂和糖基受体处理，导致形成各种 C2-酰胺糖缀合物。C2-氮转移和糖苷键形成都立体选择性地进行，允许在 C2 处引入天然和非天然酰胺官能团，同时在一锅法中形成异头键。
• Phenyloxazoline derivatives of 2-amino-2-deoxy-d-glucopyranose
  作者：Roy Gigg、Robert Conant

  DOI：10.1016/s0008-6215(00)81057-5

  日期：——