(2R,3S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-5-(benzyloxy)-3-hydroxy-2-methylpentan-1-one | 1464823-37-7

• 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)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-5-(benzyloxy)-3-hydroxy-2-methylpentan-1-one
• 英文别名: (2R,3S)-1-[(4S)-4-benzyl-2-sulfanylidene-1,3-thiazolidin-3-yl]-3-hydroxy-2-methyl-5-phenylmethoxypentan-1-one
• CAS: 1464823-37-7
• 化学式: C₂₃H₂₇NO₃S₂
• 分子量: 429.604
• InChiKey: DIARVQABWUOTQA-QMMLZNLJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  107
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,3S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-5-(benzyloxy)-3-hydroxy-2-methylpentan-1-one 在 sodium tetrahydroborate 、 bis(acetoxy)iodobenzene 、 2,2,6,6-四甲基哌啶氧化物 作用下， 以 甲醇 为溶剂， 反应 6.0h， 生成 (4S,5S,E)-ethyl 7-(benzyloxy)-5-hydroxy-4-methylhept-2-enoate
  参考文献：
  名称：

  Novel iodine catalyzed diastereoselective synthesis of trans-2,6-disubstituted tetrahydro-2H-pyrans: synthesis of C1–C13 fragment of bistramide-A

  摘要：

  A new method for the stereoselective synthesis of trans 2.6-disubstituted tetrahydro-2H-pyrans has been developed involving iodine catalyzed allylation of tetrahydro-2H-pyranol with excellent trans selectivity. The method was also applied toward the construction of C1-C13 fragment of bistramide-A in 11 steps with 21.4% overall yield. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.08.085
• 作为产物：
  描述：

  3-苄氧基丙醛 、 1-[(4R)-4-(苯基甲基)-2-硫代-3-噻唑烷基]-1-丙酮 在 四氯化钛 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 以90%的产率得到(2R,3S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-5-(benzyloxy)-3-hydroxy-2-methylpentan-1-one
  参考文献：
  名称：

  Novel iodine catalyzed diastereoselective synthesis of trans-2,6-disubstituted tetrahydro-2H-pyrans: synthesis of C1–C13 fragment of bistramide-A

  摘要：

  A new method for the stereoselective synthesis of trans 2.6-disubstituted tetrahydro-2H-pyrans has been developed involving iodine catalyzed allylation of tetrahydro-2H-pyranol with excellent trans selectivity. The method was also applied toward the construction of C1-C13 fragment of bistramide-A in 11 steps with 21.4% overall yield. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.08.085

文献信息

• Total syntheses of arenamides A, B and C
  作者：Srivari Chandrasekhar、Kurapati Sathish、Gangireddy Pavan Kumar Reddy、Prathama S. Mainkar

  DOI：10.1016/j.tetasy.2014.01.004

  日期：2014.2
• Novel iodine catalyzed diastereoselective synthesis of trans-2,6-disubstituted tetrahydro-2H-pyrans: synthesis of C1–C13 fragment of bistramide-A
  作者：Jhillu Singh Yadav、Eppa Gyanchander、Anand Kumar Mishra、Peddapuram Adithya、Saibal Das

  DOI：10.1016/j.tetlet.2013.08.085

  日期：2013.10

  A new method for the stereoselective synthesis of trans 2.6-disubstituted tetrahydro-2H-pyrans has been developed involving iodine catalyzed allylation of tetrahydro-2H-pyranol with excellent trans selectivity. The method was also applied toward the construction of C1-C13 fragment of bistramide-A in 11 steps with 21.4% overall yield. (C) 2013 Elsevier Ltd. All rights reserved.