(2R,3R)-1-benzyl-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-3,6-dihydro-2H-pyridin-3-ol | 241491-21-4

• 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: (2R,3R)-1-benzyl-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-3,6-dihydro-2H-pyridin-3-ol
• CAS: 241491-21-4
• 化学式: C₁₉H₃₁NO₂Si
• 分子量: 333.546
• InChiKey: QWRYLQAIJFKRFN-QZTJIDSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.81
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  32.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,3R)-1-benzyl-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-3,6-dihydro-2H-pyridin-3-ol 在 盐酸 、 sodium hydride 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 生成 (8S,8aS)-8-hydroxy-8,8a-dihydro-1H-oxazolo[3,4-a]pyridin-3(5H)-one
  参考文献：
  名称：

  实用合成的光学活性双环恶唑烷二基哌啶，手性构建基，可从丝氨酸制备1-脱氧天竺葵

  摘要：

  Optically active bicyclic oxazolidinylpiperidines 1a, 1b, 1c and 1d, known chiral building blocks for preparing 1-deoxyazasugars, were synthesized in high overall yield from D-serine by a method wherein the titanium(II)-mediated intramolecular nucleophilic acyl substitution and FeCl3-mediated ring enlargement of bicyclic cyclopropanols are the key reactions. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00969-7
• 作为产物：
  描述：

  (2R)-1-benzyl-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-chloropiperidin-3-one 在 sodium tetrahydroborate 、 cerium(III) chloride 、 sodium acetate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 (2R,3R)-1-benzyl-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-3,6-dihydro-2H-pyridin-3-ol
  参考文献：
  名称：

  实用合成的光学活性双环恶唑烷二基哌啶，手性构建基，可从丝氨酸制备1-脱氧天竺葵

  摘要：

  Optically active bicyclic oxazolidinylpiperidines 1a, 1b, 1c and 1d, known chiral building blocks for preparing 1-deoxyazasugars, were synthesized in high overall yield from D-serine by a method wherein the titanium(II)-mediated intramolecular nucleophilic acyl substitution and FeCl3-mediated ring enlargement of bicyclic cyclopropanols are the key reactions. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00969-7

文献信息

• Practical synthesis of optically active bicyclic oxazolidinylpiperidines, chiral building blocks for preparing 1-deoxyazasugars, from serine
  作者：Masaaki Shirai、Sentaro Okamoto、Fumie Sato

  DOI：10.1016/s0040-4039(99)00969-7

  日期：1999.7

  Optically active bicyclic oxazolidinylpiperidines 1a, 1b, 1c and 1d, known chiral building blocks for preparing 1-deoxyazasugars, were synthesized in high overall yield from D-serine by a method wherein the titanium(II)-mediated intramolecular nucleophilic acyl substitution and FeCl3-mediated ring enlargement of bicyclic cyclopropanols are the key reactions. (C) 1999 Elsevier Science Ltd. All rights reserved.