(4R,5R)-5-hydroxymethyl-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid (2,2-dimethoxy-ethyl)-methyl-amide | 908027-68-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4R,5R)-5-hydroxymethyl-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid (2,2-dimethoxy-ethyl)-methyl-amide
• 英文别名: (4R,5R)-N-(2,2-dimethoxyethyl)-5-(hydroxymethyl)-N,2,2-trimethyl-1,3-dioxolane-4-carboxamide
• CAS: 908027-68-9
• 化学式: C₁₂H₂₃NO₆
• 分子量: 277.318
• InChiKey: DEHCNCOEFPFTRZ-PSASIEDQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  77.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4R,5R)-5-hydroxymethyl-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid (2,2-dimethoxy-ethyl)-methyl-amide 在 吡啶 、 lithium aluminium tetrahydride 、 硫酸 、 silica gel 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 38.17h， 生成 (1S,5S,7R)-(3-methyl-6,8-dioxa-3-aza-bicyclo[3.2.1]oct-7-yl)-methanol
  参考文献：
  名称：

  Synthesis of a new 1,4-aminoalcohol and its use as catalyst in the enantioselective addition of organozinc to aldehydes

  摘要：

  The synthesis of a new enantiopure, conformationally constrained 1,4-aminoalcohol is reported, starting from commercially available reagents from the chiral pool. This 1,4-aminoalcohol was used as chiral ligand in the addition of Et-Zn-2 to aldehydes (best ee 98%) and in the synthesis of chiral propargylic alcohols (best ee 70%) by alkynylzinc species. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.04.010
• 作为产物：
  描述：

  D-erythronolactone acetonide 、 甲氨基乙醛缩二甲醇 在 三甲基铝 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 18.5h， 以93%的产率得到(4R,5R)-5-hydroxymethyl-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid (2,2-dimethoxy-ethyl)-methyl-amide
  参考文献：
  名称：

  Synthesis of a new 1,4-aminoalcohol and its use as catalyst in the enantioselective addition of organozinc to aldehydes

  摘要：

  The synthesis of a new enantiopure, conformationally constrained 1,4-aminoalcohol is reported, starting from commercially available reagents from the chiral pool. This 1,4-aminoalcohol was used as chiral ligand in the addition of Et-Zn-2 to aldehydes (best ee 98%) and in the synthesis of chiral propargylic alcohols (best ee 70%) by alkynylzinc species. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.04.010

文献信息

• Synthesis of a new 1,4-aminoalcohol and its use as catalyst in the enantioselective addition of organozinc to aldehydes
  作者：Dina Scarpi、Fabrizio Lo Galbo、Antonio Guarna

  DOI：10.1016/j.tetasy.2006.04.010

  日期：2006.5

  The synthesis of a new enantiopure, conformationally constrained 1,4-aminoalcohol is reported, starting from commercially available reagents from the chiral pool. This 1,4-aminoalcohol was used as chiral ligand in the addition of Et-Zn-2 to aldehydes (best ee 98%) and in the synthesis of chiral propargylic alcohols (best ee 70%) by alkynylzinc species. (c) 2006 Elsevier Ltd. All rights reserved.