(2S,3S)-3-(tert-butoxycarbonylamino)-2-(hydroxymethyl)oxetane | 1006725-83-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S,3S)-3-(tert-butoxycarbonylamino)-2-(hydroxymethyl)oxetane
• 英文别名: Tert-butyl ((2S,3S)-2-(hydroxymethyl)oxetan-3-YL)carbamate；tert-butyl N-[(2S,3S)-2-(hydroxymethyl)oxetan-3-yl]carbamate
• CAS: 1006725-83-2
• 化学式: C₉H₁₇NO₄
• 分子量: 203.238
• InChiKey: AEIVOTLOANDCEL-NKWVEPMBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  67.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,3S)-3-(tert-butoxycarbonylamino)-2-(hydroxymethyl)oxetane 在 ruthenium trichloride sodium periodate 作用下， 以 四氯化碳 、 水 、 乙腈 为溶剂， 反应 2.0h， 以30%的产率得到(2S,3S)-3-((tert-butoxycarbonyl)amino)oxetane-2-carboxylic acid
  参考文献：
  名称：

  Synthesis of epi-Oxetin via a Serine-Derived 2-Methyleneoxetane

  摘要：

  [GRAPHICS]The unique reactivity of 2-methyleneoxetanes and 1,5-dioxaspiro[3.2]hexanes has been exploited for the synthesis of epi-oxetin (26), an oxetane-containing beta-amino acid. While the preparation of the natural product oxetin (1) was the original goal, the unexpected diastereoselectivity of an precedented reduction provided the epi-oxetin framework. The methodology described herein should be amenable for the preparation of oxetin with a change in nitrogen protection.

  DOI：

  10.1021/jo7018762
• 作为产物：
  描述：

  acetic acid (2S,3S)-3-(tert-butoxycarbonylamino)oxetan-2-ylmethyl ester 在 甲醇 、 sodium methylate 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以81%的产率得到(2S,3S)-3-(tert-butoxycarbonylamino)-2-(hydroxymethyl)oxetane
  参考文献：
  名称：

  Synthesis of epi-Oxetin via a Serine-Derived 2-Methyleneoxetane

  摘要：

  [GRAPHICS]The unique reactivity of 2-methyleneoxetanes and 1,5-dioxaspiro[3.2]hexanes has been exploited for the synthesis of epi-oxetin (26), an oxetane-containing beta-amino acid. While the preparation of the natural product oxetin (1) was the original goal, the unexpected diastereoselectivity of an precedented reduction provided the epi-oxetin framework. The methodology described herein should be amenable for the preparation of oxetin with a change in nitrogen protection.

  DOI：

  10.1021/jo7018762

文献信息

• Synthesis of <i>epi</i>-Oxetin via a Serine-Derived 2-Methyleneoxetane
  作者：Marisa L. Blauvelt、Amy R. Howell

  DOI：10.1021/jo7018762

  日期：2008.1.1

  [GRAPHICS]The unique reactivity of 2-methyleneoxetanes and 1,5-dioxaspiro[3.2]hexanes has been exploited for the synthesis of epi-oxetin (26), an oxetane-containing beta-amino acid. While the preparation of the natural product oxetin (1) was the original goal, the unexpected diastereoselectivity of an precedented reduction provided the epi-oxetin framework. The methodology described herein should be amenable for the preparation of oxetin with a change in nitrogen protection.