(2S,3S,4R,5S,6S)-2-((R)-1,2-Dihydroxy-ethyl)-6-methoxy-tetrahydro-pyran-3,4,5-triol

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3S,4R,5S,6S)-2-((R)-1,2-Dihydroxy-ethyl)-6-methoxy-tetrahydro-pyran-3,4,5-triol
• 英文别名: (2S,3S,4R,5S,6S)-2-[(1R)-1,2-dihydroxyethyl]-6-methoxyoxane-3,4,5-triol
• 化学式: C₈H₁₆O₇
• 分子量: 224.211
• InChiKey: GJUAFBSAJCBGRU-LVTNRUAJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.7
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  120
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  methyl (6R)-2,3,4-tri-O-benzyl-6-(2-thiazolyl)-β-L-galactopyranoside 在 palladium on activated charcoal sodium tetrahydroborate 、 水 、 氢气 、 mercury dichloride 、 碘甲烷 作用下， 以 乙醇 为溶剂， 生成 (2S,3S,4R,5S,6S)-2-((R)-1,2-Dihydroxy-ethyl)-6-methoxy-tetrahydro-pyran-3,4,5-triol
  参考文献：
  名称：

  Diastereoselectivity in the synthesis of D-glycero-D-aldoheptoses by 2-trimethylsilylthiazole homologation from hexodialdo-1,5-pyranose derivatives

  摘要：

  对Campylobacter jejuni血清型O:23和O:36脂多糖O抗原链成分D-glycero-D-altro-heptose合成方法的探索，引导了对2-三甲基硅基噻唑同系化方法在庚糖合成中应用的研究。与从1,2:3,4-二-O-异亚丙基-α-D-半乳糖-己醛糖-1,5-吡喃糖形成1,2:3,4-二-O-异亚丙基-D-甘油-α-D-半乳糖-庚吡喃糖衍生物的差向异构选择性形成相比，具有葡萄糖和甘露糖构型的甲基2,3,4-三-O-苄基-D-己醛糖-1,5-吡喃糖苷在形成D-甘油构型化合物方面没有表现出偏好。尝试通过C-6氧化后用L-选择性还原剂将L-甘油转化为D-甘油异构体，在噻唑加合物中未能实现高差向异构选择性，但在甲基2,3,4-三-O-苄基-7-O-叔丁基二甲基硅基-D-庚吡喃糖苷的类似反应中形成了所需产物。在altro系列中进行同系化的方法因在尝试形成甲基2,3,4-三-O-苄基-α-D-altro-己醛糖-1,5-吡喃糖苷时C-5的差向异构化而受阻。从甲基α-D-葡萄糖苷成功合成了甲基D-甘油-α-D-altro-庚吡喃糖苷，通过同系化后从D-葡萄糖系列到D-altro系列构型改变实现。

  DOI：

  10.1139/v94-036

文献信息

• Diastereoselectivity in the synthesis of <scp>D</scp>-glycero-<scp>D</scp>-aldoheptoses by 2-trimethylsilylthiazole homologation from hexodialdo-1,5-pyranose derivatives
  作者：Naveen K. Khare、Ramesh K. Sood、Gerald O. Aspinall

  DOI：10.1139/v94-036

  日期：1994.1.1

  An exploration of the synthesis of D-glycero-D-altro-heptose, a constitutent of O antigen chains in lipopolysaccharides from Campylobacter jejuni serotypes O:23 and O:36 led to a study of the 2-trimethylsilylthiazole homologation procedure for heptose synthesis. In contrast to the diastereoselective formation of a 1,2:3,4-di-O-isopropylidene-D-glycero-α-D-galacto-heptopyranose derivative from 1,2:3,4-di-O-isopropylidene-α-D-galacto-hexodialdo-1,5-pyranose, methyl 2,3,4-tri-O-benzyl-D-hexodialdo-1,5-pyranosides with the gluco and manno configurations showed no preference for the formation of compounds with the D-glycero configuration. Attempts to achieve high diastereoselectivity in the conversion of L-glycero into the D-glycero isomers by oxidation at C-6 followed by reduction with L-selectride were unsuccessful with the thiazole adducts, but the desired products were formed in similar reactions of methyl 2,3,4-tri-O-benzyl-7-O-tert-butyldimethylsilyl-D-heptopyranosides. The approach to homologation in the altro series was thwarted by epimerization at C-5 in the attempted formation of methyl 2,3,4-tri-O-benzyl-α-D-altro-hexodialdo-1,5-pyranoside. The successful synthesis of methyl D-glycero-α-D-altro-heptopyranoside from methyl α-D-glucopyranoside was achieved by homologation followed by configurational alteration from the D-gluco to the D-altro series.

  对Campylobacter jejuni血清型O:23和O:36脂多糖O抗原链成分D-glycero-D-altro-heptose合成方法的探索，引导了对2-三甲基硅基噻唑同系化方法在庚糖合成中应用的研究。与从1,2:3,4-二-O-异亚丙基-α-D-半乳糖-己醛糖-1,5-吡喃糖形成1,2:3,4-二-O-异亚丙基-D-甘油-α-D-半乳糖-庚吡喃糖衍生物的差向异构选择性形成相比，具有葡萄糖和甘露糖构型的甲基2,3,4-三-O-苄基-D-己醛糖-1,5-吡喃糖苷在形成D-甘油构型化合物方面没有表现出偏好。尝试通过C-6氧化后用L-选择性还原剂将L-甘油转化为D-甘油异构体，在噻唑加合物中未能实现高差向异构选择性，但在甲基2,3,4-三-O-苄基-7-O-叔丁基二甲基硅基-D-庚吡喃糖苷的类似反应中形成了所需产物。在altro系列中进行同系化的方法因在尝试形成甲基2,3,4-三-O-苄基-α-D-altro-己醛糖-1,5-吡喃糖苷时C-5的差向异构化而受阻。从甲基α-D-葡萄糖苷成功合成了甲基D-甘油-α-D-altro-庚吡喃糖苷，通过同系化后从D-葡萄糖系列到D-altro系列构型改变实现。