(-)-(3R,4R,6R,7R,8R)-8-benzyloxy-6,7-O-isopropylidene-2-phenyl-3-p-tolyl-5-oxa-2-aza-spiro[3.4]octan-1-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂环丁烷
• 英文名称: (-)-(3R,4R,6R,7R,8R)-8-benzyloxy-6,7-O-isopropylidene-2-phenyl-3-p-tolyl-5-oxa-2-aza-spiro[3.4]octan-1-one
• 英文别名: (3aR,4'R,5R,6R,6aR)-2,2-dimethyl-4'-(4-methylphenyl)-1'-phenyl-6-phenylmethoxyspiro[6,6a-dihydro-3aH-furo[2,3-d][1,3]dioxole-5,3'-azetidine]-2'-one
• 化学式: C₂₉H₂₉NO₅
• 分子量: 471.553
• InChiKey: NAAONWRPOLGRPE-DKINLHKDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  35
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  57.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 在 氢氧化钾 、 草酰氯 、 sodium hydride 、 silver nitrate 、 溶剂黄146 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 生成 (-)-(3R,4R,6R,7R,8R)-8-benzyloxy-6,7-O-isopropylidene-2-phenyl-3-p-tolyl-5-oxa-2-aza-spiro[3.4]octan-1-one
  参考文献：
  名称：

  Stereoselective synthesis of spiro-β-lactams using d-(+)-glucose derived chiral pool: remarkable influence of the torquoelectronic effect

  摘要：

  Diastereoselective synthesis of spiro-beta-lactams via [2+2] cycloaddition reaction of imines and chiral ketenes is described. The chiral ketene was prepared from commercially available, inexpensive D-glucose. Although, theoretically four diastereomers are possible, the reaction yielded only two diastereomers stereoselectively in good to moderate yields. The stereochemical outcome of the reaction was in accordance with the torquoelectronic model. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.06.073

文献信息

• Stereoselective synthesis of spiro-β-lactams using d-(+)-glucose derived chiral pool: remarkable influence of the torquoelectronic effect
  作者：P.M. Chincholkar、Vedavati G. Puranik、A.R.A.S. Deshmukh

  DOI：10.1016/j.tet.2007.06.073

  日期：2007.9

  Diastereoselective synthesis of spiro-beta-lactams via [2+2] cycloaddition reaction of imines and chiral ketenes is described. The chiral ketene was prepared from commercially available, inexpensive D-glucose. Although, theoretically four diastereomers are possible, the reaction yielded only two diastereomers stereoselectively in good to moderate yields. The stereochemical outcome of the reaction was in accordance with the torquoelectronic model. (c) 2007 Elsevier Ltd. All rights reserved.