(2R,3S,5RS)-5,6-Epoxy-1,2-O-isopropylidenehexane-1,2,3-triol | 171032-81-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S,5RS)-5,6-Epoxy-1,2-O-isopropylidenehexane-1,2,3-triol
• 英文别名: 1,2-Anhydro-3-deoxy-5,6-O-(1-methylethylidene)-D-ribo-hexitol；(1S)-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-[(2R)-oxiran-2-yl]ethanol
• CAS: 171032-81-8
• 化学式: C₉H₁₆O₄
• 分子量: 188.224
• InChiKey: NBQCVOIWOYOAFP-GJMOJQLCSA-N

物化性质

• 沸点：
  277.8±15.0 °C(Predicted)
• 密度：
  1.157±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  51.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,3S,5RS)-5,6-Epoxy-1,2-O-isopropylidenehexane-1,2,3-triol 在 咪唑 、 4-二甲氨基吡啶 、 silica-supported sodium periodate 、 水 、 三乙基硼氢化锂 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 28.33h， 生成 (3S,4S,6S)-4-(tert-butyldimethylsilyloxy)-6-(triisopropylsilyloxy)hept-1-en-3-ol
  参考文献：
  名称：

  Synthesis of hept-6-en-2,4,5-triols and hept-6-en-2,3,5-triols

  摘要：

  In a systematic effort to establish the relative as well as absolute configurations of two natural products isolated from Asomycete Daldinia concentrica, four independent (non-antipodal) diastereomers of hept-6-en-2,4,5-triol, the structure previously proposed for the natural products, were synthesized in enantiopure forms through a chiral-pool route and their optical rotation as well as NMR data were recorded. Although these four synthetic isomers cover all possible relative configurations the originally assigned triol may have, none of them gave spectroscopic data compatible with those reported for the natural products. Similar negative results were also obtained with a group of four non-antipodal diastereomers of hept-6-en-2,3,5-triol. The genuine structures of the natural products are therefore to be re-assigned. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.01.091
• 作为产物：
  描述：

  3-deoxy-5,6-O-isopropylidene-2-O-methanesulfonyl-D-arabino-hexono-1,4-lactone 在 甲醇 、 sodium tetrahydroborate 作用下， 以 二氯甲烷 为溶剂， 生成 (2R,3S,5RS)-5,6-Epoxy-1,2-O-isopropylidenehexane-1,2,3-triol
  参考文献：
  名称：

  An Aldol Approach to the Total Synthesis of Pamamycin 621 A

  摘要：

  Pamamycin 621 A was synthesized through a convergent route, with the THF rings constructed from Evans aldols in the presence of the chiral auxiliaries without suffering racemization or elimination. The basic amino group was introduced at a late stage through reduction of an azido group with n-Bu3SnH, which also demonstrates for the first time the great potential of this largely forgotten reduction protocol in synthesis of multifunctional substrates.

  DOI：

  10.1021/ol902290v

文献信息

• Synthesis and Configuration of the Phenolic Nonadecanediol Isolated from the Resinous Exudates of<i>Heliotropium sinuatum</i>
  作者：Chao-Yuan Chen、Shao-Min Zhang、Yikang Wu、Po Gao

  DOI：10.1002/ejoc.201201184

  日期：2013.1

  The (3S,5R) and (3R,5R) isomers of the title compound were synthesized from enantiopure epoxide chiral building blocks readily accessible from D-gluconolactone. The former (a syn-1,3-diol) gave H-1 and C-13 NMR spectroscopic data and optical rotation in g

  标题化合物的 (3S,5R) 和 (3R,5R) 异构体由对映纯环氧化物手性结构单元合成，该结构单元可从 D-葡糖酸内酯轻松获得。前者（syn-1,3-diol）给出了 H-1 和 C-13 NMR 光谱数据和以 g 为单位的旋光度
• A Chiral Pool and Cross Metathesis Based Synthesis of Gingerdiols
  作者：Zhi-Li Wan、Guo-Liang Zhang、Hui-Jun Chen、Yikang Wu、Yan Li

  DOI：10.1002/ejoc.201301727

  日期：2014.4

  Both (3R,5S)- and (3R,5R)-gingerdiols were synthesized. Their 1,3-diol motifs were derived from enantiopure epoxy chiral building blocks that were readily accessible from D-gluconolactone. The effect of deuterating the OH groups of the natural isomer on its optical rotation was also examined. In the course of the syntheses of the targets, an unexplored cross-metathesis (CM) reaction of unprotected

  合成了(3R,5S)-和(3R,5R)-姜二醇。它们的 1,3-二醇基序来源于对映纯环氧手性构件，这些构件很容易从 D-葡萄糖酸内酯中获得。还研究了氘化天然异构体的 OH 基团对其旋光度的影响。在目标的合成过程中，研究了未受保护的 5-取代的 pent-1-ene-3,5-二醇的交叉复分解 (CM) 反应，其中 CM 产物很容易进行烯丙基差向异构化和氧化，因为起始二醇以前所未有的轻松重新排列成酮。这些问题最终通过在苯酚存在下在甲苯中进行 CM 反应得到解决。这些出乎意料但非常有趣的现象的原因，确定是在 5-取代的戊-1-烯-3,5-二醇的 C-5 处存在未保护的 OH 基团。还介绍了机械原理。
• An Aldol Approach to the Total Synthesis of Pamamycin 621 A
  作者：Guo-Bao Ren、Yikang Wu

  DOI：10.1021/ol902290v

  日期：2009.12.17

  Pamamycin 621 A was synthesized through a convergent route, with the THF rings constructed from Evans aldols in the presence of the chiral auxiliaries without suffering racemization or elimination. The basic amino group was introduced at a late stage through reduction of an azido group with n-Bu3SnH, which also demonstrates for the first time the great potential of this largely forgotten reduction protocol in synthesis of multifunctional substrates.
• Mulzer, Johann; Pietschmann, Catarina; Schoellhorn, Bernd, Liebigs Annalen, 1995, # 8, p. 1433 - 1440
  作者：Mulzer, Johann、Pietschmann, Catarina、Schoellhorn, Bernd、Buschmann, Juergen、Luger, Peter

  DOI：——

  日期：——
• Synthesis of hept-6-en-2,4,5-triols and hept-6-en-2,3,5-triols
  作者：Ping Jiang、Shao-Min Zhang、Lei He、Yikang Wu、Yan Li

  DOI：10.1016/j.tet.2011.01.091

  日期：2011.4

  In a systematic effort to establish the relative as well as absolute configurations of two natural products isolated from Asomycete Daldinia concentrica, four independent (non-antipodal) diastereomers of hept-6-en-2,4,5-triol, the structure previously proposed for the natural products, were synthesized in enantiopure forms through a chiral-pool route and their optical rotation as well as NMR data were recorded. Although these four synthetic isomers cover all possible relative configurations the originally assigned triol may have, none of them gave spectroscopic data compatible with those reported for the natural products. Similar negative results were also obtained with a group of four non-antipodal diastereomers of hept-6-en-2,3,5-triol. The genuine structures of the natural products are therefore to be re-assigned. (C) 2011 Elsevier Ltd. All rights reserved.