1(R),5(S),5'(R),8(S),-8-<5'-(1',2':3',4'-di-O-isopropylidene-α-L-arabino-pyranosidyl)>-1-aza-7-oxa-4-thiadioxybicyclo<3.2.1>octane

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: 1(R),5(S),5'(R),8(S),-8-<5'-(1',2':3',4'-di-O-isopropylidene-α-L-arabino-pyranosidyl)>-1-aza-7-oxa-4-thiadioxybicyclo<3.2.1>octane
• 英文别名: (1R,5S,5'R,8S)-8-(1',2':3',4'-di-O-isopropylidene-α-L-arabino-pyranosid-5'-yl)-1-aza-7-oxa-4-thiadioxybicyclo<3.2.1>octane；1(R),5(S),5'(R),8(S),-8-[5'-(1',2':3',4'-di-O-isopropylidene-α-L-arabino-pyranosidyl)]-1-aza-7-oxa-4-thiadioxybicyclo[3.2.1]octane；(5S,8S)-8-[(1S,2R,6R,8R,9S)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-8-yl]-7-oxa-4lambda6-thia-1-azabicyclo[3.2.1]octane 4,4-dioxide；(5S,8S)-8-[(1S,2R,6R,8R,9S)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-8-yl]-7-oxa-4λ6-thia-1-azabicyclo[3.2.1]octane 4,4-dioxide
• 化学式: C₁₆H₂₅NO₈S
• 分子量: 391.442
• InChiKey: KUTDEGRKTHUORX-ZRNMULPSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  26
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  101
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1(R),5(S),5'(R),8(S),-8-<5'-(1',2':3',4'-di-O-isopropylidene-α-L-arabino-pyranosidyl)>-1-aza-7-oxa-4-thiadioxybicyclo<3.2.1>octane 在 三氟乙酸 作用下， 以 水 为溶剂， 反应 1.0h， 生成 (1R,5S,5'R,8S)-8-(α-L-arabino-pyranosid-5'-yl)-1-aza-7-oxa-4-thiadioxybicyclo<3.2.1>octane
  参考文献：
  名称：

  从含氧醛肟和二乙烯基砜衍生的纯手性cycloadducts的绝对立体化学通过azaprotio cyclotransfer

  摘要：

  对手性含氧醛肟和二乙烯基砜之间的区域特异性串联硝酮生成/环加成反应的进一步研究表明，环加成非对映选择性可以通过位于肟部分α-的单个立体生成中心来控制。当α-立体中心构成环系统的一部分时，非对映选择性将大大提高，并且基于肟的α-中心处的绝对立体化学，可以准确预测主要环加合物的绝对立体化学。

  DOI：

  10.1016/0040-4020(95)00316-z
• 作为产物：
  描述：

  二乙烯基砜 、 6-deoxy-6-(N-hydroxyimino)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 以 甲苯 为溶剂， 反应 72.0h， 以2%的产率得到
  参考文献：
  名称：

  Homochiral cycloadducts derived from sugar aldoximes via nitrone intermediates

  摘要：

  Tandem nitrone generation/cycloaddition reactions between simple sugar aldoximes and divinyl sulphone in refluxing toluene have been shown to occur regiospecifically and with high diastereoselectivity in the cycloaddition step to afford homochiral cycloadducts in good yield. The process is applicable to both furanose and pyranose aldoximes. Absolute stereochemistries of the products have been determined by NOE spectroscopy and X-ray crystallography.

  DOI：

  10.1016/s0040-4020(01)80704-3

文献信息

• On the absolute stereochemistries of homochiral cycloadducts derived from oxygenated aldoximes and divinyl sulphone via azaprotio cyclotransfer
  作者：Martyn Frederickson、Ronald Grigg、Zoran Rankovic、Mark Thornton-Pett、James Redpath、Roger Crossley

  DOI：10.1016/0040-4020(95)00316-z

  日期：1995.6

  centre located α- to the oxime moiety. Diastereoselectivity is greatly enhanced when the α-stereocentre constitutes part of a ring system and the absolute stereochemistry of the major cycloadduct can be accurately predicted based upon the absolute stereochemistry at the α-centre of the oxime.

  对手性含氧醛肟和二乙烯基砜之间的区域特异性串联硝酮生成/环加成反应的进一步研究表明，环加成非对映选择性可以通过位于肟部分α-的单个立体生成中心来控制。当α-立体中心构成环系统的一部分时，非对映选择性将大大提高，并且基于肟的α-中心处的绝对立体化学，可以准确预测主要环加合物的绝对立体化学。
• Homochiral cycloadducts derived from sugar aldoximes via nitrone intermediates
  作者：Martyn Frederickson、Ronald Grigg、James Redpath、Mark Thornton-Pett

  DOI：10.1016/s0040-4020(01)80704-3

  日期：1994.5

  Tandem nitrone generation/cycloaddition reactions between simple sugar aldoximes and divinyl sulphone in refluxing toluene have been shown to occur regiospecifically and with high diastereoselectivity in the cycloaddition step to afford homochiral cycloadducts in good yield. The process is applicable to both furanose and pyranose aldoximes. Absolute stereochemistries of the products have been determined by NOE spectroscopy and X-ray crystallography.