(2R,3S,4S,5S,6S)-2-chloro-3,4,5,6-tetrakis(benzyloxy)thiepane 1,1-dioxide | 1376554-99-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R,3S,4S,5S,6S)-2-chloro-3,4,5,6-tetrakis(benzyloxy)thiepane 1,1-dioxide
• 英文别名: (2R,3S,4S,5S,6S)-2-chloro-3,4,5,6-tetrakis(phenylmethoxy)thiepane 1,1-dioxide
• CAS: 1376554-99-2
• 化学式: C₃₄H₃₅ClO₆S
• 分子量: 607.167
• InChiKey: CBDCXIXZGCGDRS-ZOHVZMGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  42
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  79.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R,3S,4S,5S,6S)-2-chloro-3,4,5,6-tetrakis(benzyloxy)thiepane 1,1-dioxide 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 0.33h， 以65%的产率得到(3R,4R,5R,6R)-3,4,5,6-tetrakis(benzyloxy)cyclohex-1-ene
  参考文献：
  名称：

  Convenient one-pot synthesis of thiosugars and their efficient conversion to polyoxygenated cycloalkenes

  摘要：

  A convenient synthesis of polyoxygenated tetrahydrothiopyrans and thiepanes from various alditol derivatives with xylo, ribo, manno, gluco, galacto, and fuco configurations is described. The preparation started from the corresponding partially protected alditols and proceeded in a 'one-pot' manner to afford the final products in 80%-95% yield. Furthermore, thiosugar compounds 2b, 2d, and 2g were converted to the optically pure polyoxygenated cycloalkenes through Ramberg-Backlund reaction in moderate to good overall yield. The procedures can be used for the preparation of polyoxygenated thiosugars and cycloalkenes on a relatively large scale. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.03.086
• 作为产物：
  描述：

  2,3,4,5-tetrakis-benzyloxyhexane-1,6-diol 在 N-氯代丁二酰亚胺 、 sodiumsulfide nonahydrate 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 四氯化碳 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.5h， 生成 (2R,3S,4S,5S,6S)-2-chloro-3,4,5,6-tetrakis(benzyloxy)thiepane 1,1-dioxide
  参考文献：
  名称：

  Convenient one-pot synthesis of thiosugars and their efficient conversion to polyoxygenated cycloalkenes

  摘要：

  A convenient synthesis of polyoxygenated tetrahydrothiopyrans and thiepanes from various alditol derivatives with xylo, ribo, manno, gluco, galacto, and fuco configurations is described. The preparation started from the corresponding partially protected alditols and proceeded in a 'one-pot' manner to afford the final products in 80%-95% yield. Furthermore, thiosugar compounds 2b, 2d, and 2g were converted to the optically pure polyoxygenated cycloalkenes through Ramberg-Backlund reaction in moderate to good overall yield. The procedures can be used for the preparation of polyoxygenated thiosugars and cycloalkenes on a relatively large scale. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.03.086

文献信息

• Convenient one-pot synthesis of thiosugars and their efficient conversion to polyoxygenated cycloalkenes
  作者：Jingjing Zhang、Youhong Niu、Xiaoping Cao、Xin-Shan Ye

  DOI：10.1016/j.tet.2012.03.086

  日期：2012.6

  A convenient synthesis of polyoxygenated tetrahydrothiopyrans and thiepanes from various alditol derivatives with xylo, ribo, manno, gluco, galacto, and fuco configurations is described. The preparation started from the corresponding partially protected alditols and proceeded in a 'one-pot' manner to afford the final products in 80%-95% yield. Furthermore, thiosugar compounds 2b, 2d, and 2g were converted to the optically pure polyoxygenated cycloalkenes through Ramberg-Backlund reaction in moderate to good overall yield. The procedures can be used for the preparation of polyoxygenated thiosugars and cycloalkenes on a relatively large scale. (C) 2012 Elsevier Ltd. All rights reserved.