3-azido-3,5,6-trideoxy-1,2-O-isopropylidene-α-D-ribo-hexofuran-5-ene | 163592-80-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-azido-3,5,6-trideoxy-1,2-O-isopropylidene-α-D-ribo-hexofuran-5-ene
• 英文别名: (3aR,5R,6R,6aR)-6-azido-5-ethenyl-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole
• CAS: 163592-80-1
• 化学式: C₉H₁₃N₃O₃
• 分子量: 211.221
• InChiKey: UYXJWIQEAJEUAF-WCTZXXKLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  42
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  壬烯 、 3-azido-3,5,6-trideoxy-1,2-O-isopropylidene-α-D-ribo-hexofuran-5-ene 在 ruthenium carbene complex 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 以83%的产率得到(3aR,5R,6R,6aR)-6-azido-2,2-dimethyl-5-[(E)-non-1-enyl]-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole
  参考文献：
  名称：

  从D-葡萄糖：烯烃交叉复分解方法高效合成D-赤型和D-苏式-神经鞘氨醇。

  摘要：

  [反应：见正文]使用D-葡萄糖衍生的结构单元和长链末端烯烃，通过E-选择性烯烃交叉复分解合成D-赤型和D-苏式-鞘氨醇。

  DOI：

  10.1021/ol052320z
• 作为产物：
  描述：

  3-azido-3-deoxy-1,2-O-isopropylidene-α-D-allofuranose 在 ruthenium trichloride 、 sodium tetrahydroborate 、 sodium periodate 、 氯化亚砜 、 三乙胺 作用下， 以 甲醇 、 四氯化碳 、 二氯甲烷 、 水 、 丙酮 、 乙腈 为溶剂， 反应 3.0h， 生成 3-azido-3,5,6-trideoxy-1,2-O-isopropylidene-α-D-ribo-hexofuran-5-ene
  参考文献：
  名称：

  Applications of Cyclic Sulfates of vic-Diols:  Synthesis of Episulfides, Olefins, and Thio Sugars

  摘要：

  A new efficient and expeditious one-pot synthesis of thiiranes and olefins from cyclic sulfates of vic-diols is described. Opening of cyclic sulfates with potassium thioacetate or potassium thiocyanate followed by treatment with sodium methoxide led to episulfides. Olefins were obtained when potassium selenocyanate was used as nucleophile, and the obtained monoesters were treated with sodium borohydride. This method was applied to acyclic polyols derived from chiral glycerine, 1,2-isopropylidenehexofuranoses with different subtituents at C-3, and dimethyl acetals derived from pentoses and hexoses. The methodology is highly versatile, and its applicability has been demonstrated by the synthesis of different 4- and 5-thiosugars by opening of the thiirane ring with sodium acetate or lithium aluminum hydride. Reduction with lithium aluminum hydride of the thiocyanate sulfate potassium salt obtained by the opening of cyclic sulfate with KSCN allowed the direct synthesis of 5-deoxy-4-thio- and 6-deoxy-5-thiosugars. Cyclic thiosugars with the sulfur atom in the ring are obtained by acidic hydrolysis of the 5-thiol derivatives of 1,2-O-isopropylidenehexofuranoses and 4-thiopentose dimethyl acetals. Using this method, an efficient synthesis of 5-thio-L-fucose as well as the synthesis of 2,5-dideoxy-4-thiofuranose is described.

  DOI：

  10.1021/jo962066b

文献信息

• Synthesis of sugar episulfides and olefins from via-diols via cyclic sulfates
  作者：Francisco Santoyo-González、Francisco García-Calvo-Flores、Pilar García-Mendoza、Fernando Hernandez-Mateo、Joaquín Isac-García、Ma Dolores Pérez-Alvarez

  DOI：10.1039/c39950000461

  日期：——

  Cyclic sulfates of vic-diols are transformed in one-pot into sugar episulfides by treatment with potassium thioacetate or thiourea followed by reaction with sodium methoxide; reaction of these cyclic sulfates with potassium selenocyanate followed by treatment with sodium borohydride allows the synthesis of sugar olefins.

  的环硫酸酯VIC -diols通过与硫代乙酸钾或治疗转化在一锅转化为糖环硫化物的硫脲，接着用甲醇钠反应; 这些环状硫酸盐与硒氰酸钾反应，然后用硼氢化钠处理，可以合成糖烯烃。
• Applications of Cyclic Sulfates of <i>vic</i>-Diols:  Synthesis of Episulfides, Olefins, and Thio Sugars
  作者：Francisco G. Calvo-Flores、Pilar García-Mendoza、Fernando Hernández-Mateo、Joaquín Isac-García、Francisco Santoyo-González

  DOI：10.1021/jo962066b

  日期：1997.6.13

  A new efficient and expeditious one-pot synthesis of thiiranes and olefins from cyclic sulfates of vic-diols is described. Opening of cyclic sulfates with potassium thioacetate or potassium thiocyanate followed by treatment with sodium methoxide led to episulfides. Olefins were obtained when potassium selenocyanate was used as nucleophile, and the obtained monoesters were treated with sodium borohydride. This method was applied to acyclic polyols derived from chiral glycerine, 1,2-isopropylidenehexofuranoses with different subtituents at C-3, and dimethyl acetals derived from pentoses and hexoses. The methodology is highly versatile, and its applicability has been demonstrated by the synthesis of different 4- and 5-thiosugars by opening of the thiirane ring with sodium acetate or lithium aluminum hydride. Reduction with lithium aluminum hydride of the thiocyanate sulfate potassium salt obtained by the opening of cyclic sulfate with KSCN allowed the direct synthesis of 5-deoxy-4-thio- and 6-deoxy-5-thiosugars. Cyclic thiosugars with the sulfur atom in the ring are obtained by acidic hydrolysis of the 5-thiol derivatives of 1,2-O-isopropylidenehexofuranoses and 4-thiopentose dimethyl acetals. Using this method, an efficient synthesis of 5-thio-L-fucose as well as the synthesis of 2,5-dideoxy-4-thiofuranose is described.
• An Efficient Synthesis of <scp>d</scp>-<i>e</i><i>rythro</i>- and <scp>d</scp>-<i>t</i><i>hreo</i>-Sphingosine from <scp>d</scp>-Glucose:  Olefin Cross-Metathesis Approach
  作者：Vinod D. Chaudhari、K. S. Ajish Kumar、Dilip D. Dhavale

  DOI：10.1021/ol052320z

  日期：2005.12.1

  [reaction: see text] The D-erythro- and D-threo-sphingosine were synthesized via E-selective olefin cross-metathesis using a D-glucose-derived building block and long-chain terminal alkene.

  [反应：见正文]使用D-葡萄糖衍生的结构单元和长链末端烯烃，通过E-选择性烯烃交叉复分解合成D-赤型和D-苏式-鞘氨醇。