(4R)-4-[(3aR,5S,6aR)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-1,3,2-dioxathiolane 2,2-dioxide | 163592-75-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机硫酸及其衍生物
• 英文名称: (4R)-4-[(3aR,5S,6aR)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-1,3,2-dioxathiolane 2,2-dioxide
• CAS: 163592-75-4
• 化学式: C₉H₁₄O₇S
• 分子量: 266.272
• InChiKey: QYSLIGSAGYPFCB-LXGUWJNJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  17
• 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：
  88.7
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (4R)-4-[(3aR,5S,6aR)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-1,3,2-dioxathiolane 2,2-dioxide 在 sodium tetrahydroborate 作用下， 以 甲醇 、 丙酮 为溶剂， 生成 3,5,6-trideoxy-1,2-O-isopropylidene-α-D-ribo-hex-5-enofuranoside
  参考文献：
  名称：

  经由环状硫酸盐，通过二元醇从二醇中合成糖环硫化物和烯烃

  摘要：

  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。

  DOI：

  10.1039/c39950000461
• 作为产物：
  描述：

  3-deoxy-1,2-O-isopropylidene-D-glucose 在 ruthenium trichloride 、 sodium periodate 、 thionyl diimidazole 作用下， 生成 (4R)-4-[(3aR,5S,6aR)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-1,3,2-dioxathiolane 2,2-dioxide
  参考文献：
  名称：

  Synthesis of 3-trialkylsilyl pyrazoles from β-oxo acylsilanes

  摘要：

  The synthesis of beta -oxo acylsilanes via cyclic sulfates is described and applied to carbohydrates. These compounds are used for the synthesis of new silylated pyrazoles linked to a carbohydrate moiety by the addition of hydrazines. The regiochemistry of the reaction was determined by NMR analyses (H-1/C-13 and H-1/N-15 correlations). (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01724-x

文献信息

• Synthesis of 3,6-anhydro sugars from cyclic sulfites and sulfates and their applications in the preparation of bicyclonucleoside analogues of ddC and ddA
  作者：M.Pineda Molas、M.Isabel Matheu、Sergio Castillón、Joaquín Isac-García、Fernando Hernández-Mateo、Francisco G. Calvo-Flores、Francisco Santoyo-González

  DOI：10.1016/s0040-4020(99)00911-4

  日期：1999.12

  Cyclic sulfates 21–23 and sulfite 27 derived from glucofuranose lead to the 3,6-anhydrosugar 28 in excellent yields when treated with sodium sulfite or in basic media. When treated with sodium sulfite, the 3-deoxy derivative 24 fails to give the intramolecular cyclization which leads to the anhydrosugars. Instead it gives the disulfonate derivative 26. 28 was used as starting material to prepare bicyclonucleosides

  当用亚硫酸钠或在碱性介质中处理时，衍生自葡糖呋喃糖的环状硫酸盐21 – 23和亚硫酸盐27以极高的产率生成3,6-脱水糖28。当用亚硫酸钠处理时，3-脱氧衍生物24不能产生分子内环化作用，从而导致脱水糖。相反，它给出二磺酸盐衍生物26。使用28作为起始原料制备双环核苷43和46，它们是抗HIV药物ddC和ddA的类似物。
• 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.