benzyl (2S,3R)-3-hydroxy-2-(hydroxymethyl)-3,6-dihydro-2H-pyridine-1-carboxylate | 1346679-04-6

• 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 (2S,3R)-3-hydroxy-2-(hydroxymethyl)-3,6-dihydro-2H-pyridine-1-carboxylate
• CAS: 1346679-04-6
• 化学式: C₁₄H₁₇NO₄
• 分子量: 263.293
• InChiKey: DWPZSFTZSLQYQV-QWHCGFSZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  70
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  benzyl (2S,3R)-3-hydroxy-2-(hydroxymethyl)-3,6-dihydro-2H-pyridine-1-carboxylate 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以90%的产率得到(8R,8aS)-8-hydroxy-8,8a-dihydro-1H-oxazolo[3,4-a]pyridin-3(5H)-one
  参考文献：
  名称：

  Chiron approach strategy to the bicyclic oxazolidinylpiperidine: a building block for preparing mono- and bi-cyclic iminosugars

  摘要：

  A chiron approach to the synthesis of bicyclic oxazolidinylpiperidine, a synthetically potential building block for preparing mono- and bi-cyclic iminosugars, is reported from D-glucose using ring closing metathesis as the key step. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.09.039
• 作为产物：
  描述：

  3-[(allyl)(benzyloxycarbonyl)amino]-3-deoxy-1,2-O-isopropylidene-α-D-allo-1,4-furanose 在 咪唑 、 sodium tetrahydroborate 、 sodium periodate 、 碘 、 三苯基膦 、 三氟乙酸 作用下， 以 甲醇 、 水 、 丙酮 、 甲苯 为溶剂， 反应 12.0h， 生成 benzyl (2S,3R)-3-hydroxy-2-(hydroxymethyl)-3,6-dihydro-2H-pyridine-1-carboxylate 、 (8R,8aS)-8-hydroxy-8,8a-dihydro-1H-oxazolo[3,4-a]pyridin-3(5H)-one
  参考文献：
  名称：

  Chiron approach strategy to the bicyclic oxazolidinylpiperidine: a building block for preparing mono- and bi-cyclic iminosugars

  摘要：

  A chiron approach to the synthesis of bicyclic oxazolidinylpiperidine, a synthetically potential building block for preparing mono- and bi-cyclic iminosugars, is reported from D-glucose using ring closing metathesis as the key step. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.09.039

文献信息

• Chiron approach strategy to the bicyclic oxazolidinylpiperidine: a building block for preparing mono- and bi-cyclic iminosugars
  作者：Navnath B. Kalamkar、Dilip D. Dhavale

  DOI：10.1016/j.tetlet.2011.09.039

  日期：2011.11

  A chiron approach to the synthesis of bicyclic oxazolidinylpiperidine, a synthetically potential building block for preparing mono- and bi-cyclic iminosugars, is reported from D-glucose using ring closing metathesis as the key step. (C) 2011 Elsevier Ltd. All rights reserved.