Acetic acid (3aR,5S,6S,6aR)-5-((R)-2,2-dioxo-2λ⁶-[1,3,2]dioxathiolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester | 163592-74-3

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: Acetic acid (3aR,5S,6S,6aR)-5-((R)-2,2-dioxo-2λ⁶-[1,3,2]dioxathiolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester
• 英文别名: [(3aR,5S,6S,6aR)-5-[(4R)-2,2-dioxo-1,3,2-dioxathiolan-4-yl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl] acetate
• CAS: 163592-74-3
• 化学式: C₁₁H₁₆O₉S
• 分子量: 324.309
• InChiKey: GFVXDYHWNBPSGN-HOTMZDKISA-N

物化性质

• 沸点：
  428.9±45.0 °C(Predicted)
• 密度：
  1.53±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  115
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  Acetic acid (3aR,5S,6S,6aR)-5-((R)-2,2-dioxo-2λ⁶-[1,3,2]dioxathiolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester 在 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 、 丙酮 为溶剂， 生成 5,6-Didesoxy-5,6-epithio-1,2-O-isopropyliden-α-L-idofuranose
  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：

  1,2-o-异亚丙基-alpha-d-呋喃葡萄糖-3-乙酸酯 在 ruthenium trichloride 、 sodium periodate 、 氯化亚砜 、 三乙胺 作用下， 以 四氯化碳 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 3.0h， 生成 Acetic acid (3aR,5S,6S,6aR)-5-((R)-2,2-dioxo-2λ⁶-[1,3,2]dioxathiolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester
  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 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。
• Completely regioselective synthesis of 5- and 6- amino and fluoro-hexofuranoses via cyclic sulphates
  作者：José Fuentes、Manuel Angulo、M Angeles Pradera

  DOI：10.1016/s0040-4039(98)01529-9

  日期：1998.9

  The nucleophilic opening of new and previously described 5,6- and 3,5-glucohexofuranose cyclic sulphates is a regioselective and efficient way to prepare 6- and 5-azido(amino)- and 6- and 5-fluoro-aldofuranose derivatives (D-gluco and L-ido configurations). (C) 1998 Published by Elsevier Science Ltd. All rights reserved.
• Cyclic sulfates in the regioselective synthesis of 5- and 6-amino and 5- and 6-fluorohexofuranoses
  作者：José Fuentes、Manuel Angulo、M Angeles Pradera

  DOI：10.1016/s0008-6215(99)00124-x

  日期：1999.6

  Cyclic sulfates of 5,6- and 3,5-D-glucofuranose were used to prepare 6- and 5-azido (amino) and 6- and ti-fluoro derivatives of 1,2-O-isopropylidenehexofuranoses (D-gluco and L-ino configurations). The reactions were completely regioselective and, in the case of stereogenic centers (substitution at C-5), completely stereoselective. (C) 1999 Elsevier Science Ltd, All rights reserved.