(S)-4-O-allyl-1,2-O-isopropylidenebutane-1,2,4-triol | 135513-67-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-4-O-allyl-1,2-O-isopropylidenebutane-1,2,4-triol
• 英文别名: (4S)-2,2-dimethyl-4-(2-prop-2-enoxyethyl)-1,3-dioxolane
• CAS: 135513-67-6
• 化学式: C₁₀H₁₈O₃
• 分子量: 186.251
• InChiKey: UPYCPNFSOMHVNR-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.73
• 重原子数：
  13.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  27.69
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (S)-4-O-allyl-1,2-O-isopropylidenebutane-1,2,4-triol 在 盐酸 、 sodium hydroxide 、 偶氮二甲酸二异丙酯 、 Amberlite IR-120 resin 、 三苯基膦 作用下， 以 乙醇 、 水 、 苯 为溶剂， 反应 0.5h， 生成 (S)-4-O-allyl-1-O-benzylbutane-1,2,4-triol
  参考文献：
  名称：

  1',2'-Secothymidines. The preparation of 2,3'-anhydro derivatives and the formation of two unusual dimeric products

  摘要：

  2,2'- and 2,3'-anhydropyrimidine nucleosides are rigid compounds that are restricted to the syn conformation. In certain cases, this enforced conformational rigidity has led to biologically active compounds. To capitalize on this rationale, attempts were made to prepare the corresponding anhydro analogues of 1',2'-secothymidine. Starting with the functionalized butanetetrols and -triols (1a-c and 2a-c), derived from D-isoascorbic acid, the 1',2'-seco nucleoside tosylates 9a-c were prepared. While attempts to form the 2,3'-anhydro derivatives (10a and 12) were successful, no 2,2'-anhydro analogues could be obtained even under a variety of reaction conditions. Instead, unusual dimeric compounds were formed whose structures were confirmed by C-13 NMR and mass spectrometry. The dimerization reaction does not appear to have been previously reported.

  DOI：

  10.1021/jo00015a017
• 作为产物：
  描述：

  (S)-4-(2-羟乙基)-2,2-二甲基-1,3-二氧戊环 、 3-溴丙烯 在 sodium hydride 作用下， 生成 (S)-4-O-allyl-1,2-O-isopropylidenebutane-1,2,4-triol
  参考文献：
  名称：

  1',2'-Secothymidines. The preparation of 2,3'-anhydro derivatives and the formation of two unusual dimeric products

  摘要：

  2,2'- and 2,3'-anhydropyrimidine nucleosides are rigid compounds that are restricted to the syn conformation. In certain cases, this enforced conformational rigidity has led to biologically active compounds. To capitalize on this rationale, attempts were made to prepare the corresponding anhydro analogues of 1',2'-secothymidine. Starting with the functionalized butanetetrols and -triols (1a-c and 2a-c), derived from D-isoascorbic acid, the 1',2'-seco nucleoside tosylates 9a-c were prepared. While attempts to form the 2,3'-anhydro derivatives (10a and 12) were successful, no 2,2'-anhydro analogues could be obtained even under a variety of reaction conditions. Instead, unusual dimeric compounds were formed whose structures were confirmed by C-13 NMR and mass spectrometry. The dimerization reaction does not appear to have been previously reported.

  DOI：

  10.1021/jo00015a017

文献信息

• CICHY, ANNE F.;SAIBABA, RACHA;EL, SUBBAGH HUSSEIN I.;PANZICA, RAYMOND P.;+, J. ORG. CHEM., 56,(1991) N5, C. 4653-4658
  作者：CICHY, ANNE F.、SAIBABA, RACHA、EL, SUBBAGH HUSSEIN I.、PANZICA, RAYMOND P.、+

  DOI：——

  日期：——