(4R,5R,4'R)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-[4,4']bi[[1,3,2]dioxathiolanyl] 2,2,2',2'-tetraoxide | 292082-58-7

• 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,5R,4'R)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-[4,4']bi[[1,3,2]dioxathiolanyl] 2,2,2',2'-tetraoxide
• 英文别名: (4R,5R)-4-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-5-[(4R)-2,2-dioxo-1,3,2-dioxathiolan-4-yl]-1,3,2-dioxathiolane 2,2-dioxide
• CAS: 292082-58-7
• 化学式: C₉H₁₄O₁₀S₂
• 分子量: 346.336
• InChiKey: PWUWONIUNSMENR-WCTZXXKLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  140
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (4R,5R,4'R)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-[4,4']bi[[1,3,2]dioxathiolanyl] 2,2,2',2'-tetraoxide 在 sodium sulfide 作用下， 生成 Sulfuric acid mono-[(3S,4R,5S)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-sulfooxy-tetrahydro-thiophen-3-yl] ester
  参考文献：
  名称：

  Heterocyclisation of free or partially protected alditols via their bis-cyclic sulfate derivatives. Versatile synthesis of aza and thiodeoxyanhydroalditol with erythro, threo, arabino, gulo, talo or manno configuration

  摘要：

  The bis-cyclic sulfate derivatives of erythritol (1), D,L-threitol (5), 3,4-di-O-benzyl-D-mannitol (9), 1,2-O-isopropylidene-D-mannitol (14) and 1-O-benzyl-D,L-xylitol (18) were submitted to nucleophilic attack by allylamine or sodium sulfide. In both cases, heterocyclisation occurred and aza or thioanhydrodeoxyalditols were obtained in moderate to good yields (40 to 89%). With compound 9, 1,5-anhydro-5-thio-L-gulitol (12) was obtained as the main product, a result that is in contrast with previous results reported in the literature using bis-epoxide as bielectrophile intermediate.(1) (C) 2000 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(00)00791-7
• 作为产物：
  描述：

  1,2-O-异亚丙基-D-甘露醇 在 ruthenium trichloride 、 sodium periodate 、 双(咪唑-1-基)亚砜 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 0.5h， 生成 (4R,5R,4'R)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-[4,4']bi[[1,3,2]dioxathiolanyl] 2,2,2',2'-tetraoxide
  参考文献：
  名称：

  Heterocyclisation of free or partially protected alditols via their bis-cyclic sulfate derivatives. Versatile synthesis of aza and thiodeoxyanhydroalditol with erythro, threo, arabino, gulo, talo or manno configuration

  摘要：

  The bis-cyclic sulfate derivatives of erythritol (1), D,L-threitol (5), 3,4-di-O-benzyl-D-mannitol (9), 1,2-O-isopropylidene-D-mannitol (14) and 1-O-benzyl-D,L-xylitol (18) were submitted to nucleophilic attack by allylamine or sodium sulfide. In both cases, heterocyclisation occurred and aza or thioanhydrodeoxyalditols were obtained in moderate to good yields (40 to 89%). With compound 9, 1,5-anhydro-5-thio-L-gulitol (12) was obtained as the main product, a result that is in contrast with previous results reported in the literature using bis-epoxide as bielectrophile intermediate.(1) (C) 2000 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(00)00791-7

文献信息

• Heterocyclisation of free or partially protected alditols via their bis-cyclic sulfate derivatives. Versatile synthesis of aza and thiodeoxyanhydroalditol with erythro, threo, arabino, gulo, talo or manno configuration
  作者：Virginie Glaçon、Mohammed Benazza、Daniel Beaupère、Gilles Demailly

  DOI：10.1016/s0040-4039(00)00791-7

  日期：2000.6

  The bis-cyclic sulfate derivatives of erythritol (1), D,L-threitol (5), 3,4-di-O-benzyl-D-mannitol (9), 1,2-O-isopropylidene-D-mannitol (14) and 1-O-benzyl-D,L-xylitol (18) were submitted to nucleophilic attack by allylamine or sodium sulfide. In both cases, heterocyclisation occurred and aza or thioanhydrodeoxyalditols were obtained in moderate to good yields (40 to 89%). With compound 9, 1,5-anhydro-5-thio-L-gulitol (12) was obtained as the main product, a result that is in contrast with previous results reported in the literature using bis-epoxide as bielectrophile intermediate.(1) (C) 2000 Published by Elsevier Science Ltd.