2,3:5,6-di-O-isopropylidene-d-mannofuranose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3:5,6-di-O-isopropylidene-d-mannofuranose
• 英文别名: 2,3:5,6-di-O-isopropylidene-D-talofuranose；2,3,5,6-di-O-isopropylidene-L-idofuranose；(3aS,6S,6aS)-6-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-ol
• 化学式: C₁₂H₂₀O₆
• 分子量: 260.287
• InChiKey: JWWCLCNPTZHVLF-YBEHEVOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,3:5,6-di-O-isopropylidene-d-mannofuranose 在 咪唑 、 二异丁基氢化铝 、 三乙胺 、 苯甲酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 99.92h， 生成 (E)-3-((4R,5R)-5-((R)-((tert-butyldimethylsilyl)oxy)((R)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)allyl methanesulfonate
  参考文献：
  名称：

  从d-甘露糖全合成l-阿拉伯糖-，l-核糖-C 18-植物鞘氨醇，ent -2- epi -jaspine B和3- epi -jaspine B的通用方法

  摘要：

  对于受保护的全合成的常用策略升-阿拉伯糖-和升-核糖-C 18 -phytosphingosine（8和9，分别地），盐酸的盐耳鼻喉科-2-外延-jaspine B（ENT - 6）和3-实现了有效利用柔性构件26和27的Epi- jaspine B（7）。该方法的关键步骤是烯丙基三氯乙酰亚胺酸酯21和硫氰酸酯22的[3,3]σ重排。，将其与已知的2,3衍生自：5,6-二- ö异亚丙基d -mannofuranose 18为手性的来源。利用维蒂希反应来安装侧链功能。

  DOI：

  10.1016/j.tet.2013.07.028
• 作为产物：
  描述：

  2,3:5,6-二-O-异亚丙基-D-甘露糖酸-1,4-内酯 在 4-二甲氨基吡啶 、 二异丁基氢化铝 、 甲基磺酰氯 、 三乙胺 作用下， 以 乙酸乙酯 、 甲苯 为溶剂， 反应 9.0h， 生成 2,3:5,6-di-O-isopropylidene-d-mannofuranose
  参考文献：
  名称：

  One-pot inversion of d -mannono-1,4-lactone for the practical synthesis of l -ribose

  摘要：

  L-Ribose was synthesized in a concise manner from D-mannono-1,4-lactone using one-pot inversion conditions. Treatment of D-mannono-1,4-lactone with piperidine, followed by mesylation-induced S(N)2-type O-alkylation afforded the desired one-pot inversion in an optimum yield, and the following straightforward transformations provided L-ribose in good yields. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)00552-5

文献信息

• Synthesis of 2-aminocyclopropyl pyrrolidines from glycoaminonitriles
  作者：Delphine Declerck、Solen Josse、Albert Nguyen Van Nhien、Denis Postel

  DOI：10.1016/j.tetlet.2009.02.135

  日期：2009.5

  We have developed an expedient method for the synthesis of 2-aminocyclopropyl pyrrolidines from carbohydrate-derived α-aminonitriles involving up to five or six steps, the key step being the titanium-mediated aminocyclopropanation on the aminonitrile moiety, followed by cleavage of the protecting groups.

  我们已经开发了一种从碳水化合物衍生的α-氨基腈合成2个氨基环丙基吡咯烷的简便方法，涉及多达五或六个步骤，关键步骤是在氨基腈部分进行钛介导的氨基环丙烷化，然后裂解保护基。
• Novel Synthesis of <scp>l</scp>-Ribose from <scp>d</scp>-Mannono-1,4-lactone
  作者：Hideyo Takahashi、Yoshinori Iwai、Yuko Hitomi、Shiro Ikegami

  DOI：10.1021/ol026141i

  日期：2002.7.1

  [GRAPHICS]D-Mannono-1,4-lactone was efficiently converted into L-ribose in eight steps. A key step of this synthesis is the cyclization of a gamma-hydroxyalkoxamate under Mitsunobu conditions. It is noteworthy that the O-alkylation product was obtained in 94% yield and that none of the N-alkylation product was detected in this cyclization.
• A common approach to the total synthesis of l-arabino-, l-ribo-C18-phytosphingosines, ent-2-epi-jaspine B and 3-epi-jaspine B from d-mannose
  作者：Miroslava Martinková、Kvetoslava Pomikalová、Jozef Gonda、Mária Vilková

  DOI：10.1016/j.tet.2013.07.028

  日期：2013.9

  for the total syntheses of the protected l-arabino- and l-ribo-C18-phytosphingosine (8 and 9, respectively), HCl salts of ent-2-epi-jaspine B (ent-6) and 3-epi-jaspine B (7) with efficient use of both flexible building blocks 26 and 27 was achieved. The key step of this approach was [3,3]-sigmatropic rearrangement of allylic trichloroacetimidate 21 and thiocyanate 22, which were derived from the known

  对于受保护的全合成的常用策略升-阿拉伯糖-和升-核糖-C 18 -phytosphingosine（8和9，分别地），盐酸的盐耳鼻喉科-2-外延-jaspine B（ENT - 6）和3-实现了有效利用柔性构件26和27的Epi- jaspine B（7）。该方法的关键步骤是烯丙基三氯乙酰亚胺酸酯21和硫氰酸酯22的[3,3]σ重排。，将其与已知的2,3衍生自：5,6-二- ö异亚丙基d -mannofuranose 18为手性的来源。利用维蒂希反应来安装侧链功能。
• One-pot inversion of d -mannono-1,4-lactone for the practical synthesis of l -ribose
  作者：Myung Joon Seo、Joungho An、Jae Hak Shim、Guncheol Kim

  DOI：10.1016/s0040-4039(03)00552-5

  日期：2003.4

  L-Ribose was synthesized in a concise manner from D-mannono-1,4-lactone using one-pot inversion conditions. Treatment of D-mannono-1,4-lactone with piperidine, followed by mesylation-induced S(N)2-type O-alkylation afforded the desired one-pot inversion in an optimum yield, and the following straightforward transformations provided L-ribose in good yields. (C) 2003 Elsevier Science Ltd. All rights reserved.