benzyl N-prop-2-enyl-N-[(3R,4R,5S)-1,3,4,5-tetrakis(phenylmethoxy)hept-6-en-2-yl]carbamate | 669015-47-8

• 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: benzyl N-prop-2-enyl-N-[(3R,4R,5S)-1,3,4,5-tetrakis(phenylmethoxy)hept-6-en-2-yl]carbamate
• CAS: 669015-47-8
• 化学式: C₄₆H₄₉NO₆
• 分子量: 711.898
• InChiKey: XFVYYMVBPZVMAT-JGAWIVKWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.5
• 重原子数：
  53
• 可旋转键数：
  23
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  66.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  benzyl N-prop-2-enyl-N-[(3R,4R,5S)-1,3,4,5-tetrakis(phenylmethoxy)hept-6-en-2-yl]carbamate 在 Grubbs catalyst first generation 作用下， 以 二氯甲烷 为溶剂， 反应 30.0h， 以73%的产率得到benzyl (3R,4R,5S,6Z)-3,4,5-tris(phenylmethoxy)-2-(phenylmethoxymethyl)-3,4,5,8-tetrahydro-2H-azocine-1-carboxylate
  参考文献：
  名称：

  Synthesis and biological evaluation of the first example of an eight-membered iminoalditol

  摘要：

  The synthesis of the first examples of eight-membered iminoalditols has been achieved from 2,3,4,6-tetra-O-benzyl-D-glucopyranose by way of a ring-closing metathesis. The (2R,3R,4R,5S)-2-hydroxymethyl-azocane-3,4,5-triol (3a), which has the D-gluco configuration for C-2-C-5 and appears to exist predominantly in a boat-chair conformation, is a weak inhibitor of glycosidases. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.10.195
• 作为产物：
  描述：

  1,3,4,5-tetra-O-benzyl-6,7-dideoxy-L-xylo-hept-6-en-2-ulose 在 3 A molecular sieve 、 sodium cyanoborohydride 、 potassium carbonate 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 136.0h， 生成 benzyl N-prop-2-enyl-N-[(3R,4R,5S)-1,3,4,5-tetrakis(phenylmethoxy)hept-6-en-2-yl]carbamate
  参考文献：
  名称：

  Synthesis and biological evaluation of the first example of an eight-membered iminoalditol

  摘要：

  The synthesis of the first examples of eight-membered iminoalditols has been achieved from 2,3,4,6-tetra-O-benzyl-D-glucopyranose by way of a ring-closing metathesis. The (2R,3R,4R,5S)-2-hydroxymethyl-azocane-3,4,5-triol (3a), which has the D-gluco configuration for C-2-C-5 and appears to exist predominantly in a boat-chair conformation, is a weak inhibitor of glycosidases. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.10.195