tert-butyl (2E)-2,3,4,7-tetradeoxy-7-iodo-D-ribo-hept-2-enoate | 208036-05-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: tert-butyl (2E)-2,3,4,7-tetradeoxy-7-iodo-D-ribo-hept-2-enoate
• 英文别名: tert-butyl (E,5S,6S)-5,6-dihydroxy-7-iodohept-2-enoate
• CAS: 208036-05-9
• 化学式: C₁₁H₁₉IO₄
• 分子量: 342.174
• InChiKey: HRUWKBYVXHPUCS-HNEWHRDISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl (2E)-2,3,4,7-tetradeoxy-7-iodo-D-ribo-hept-2-enoate 在 三乙基硼 、 三正丁基氢锡 、 二异丁基氢化铝 、 对甲苯磺酸 作用下， 以 正己烷 、 甲苯 为溶剂， 反应 33.0h， 生成 2-((3aR,5R,6aS)-2,2-Diethyl-tetrahydro-cyclopenta[1,3]dioxol-5-yl)-ethanol
  参考文献：
  名称：

  Synthesis of vinylcyclopentanes via samarium(II) mediated tandem reactions

  摘要：

  In the presence of either visible light or HMPA, SMI2 reacts with some carbohydrate derived w-iodoallylic alcohols, and their acetylated derivatives, to give vinylcyclopentanediol and vinylcyclopentanetriol derivatives. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.06.099
• 作为产物：
  描述：

  2-脱氧-D-核糖 在 N-碘代丁二酰亚胺 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 tert-butyl (2E)-2,3,4,7-tetradeoxy-7-iodo-D-ribo-hept-2-enoate
  参考文献：
  名称：

  碘化sa（II）介导的碳水化合物衍生的ω-卤代-α，β-不饱和酯的转化的化学选择性和非对映选择性的研究

  摘要：

  在各种条件下，SmI 2还原了一些碳水化合物衍生的ω-溴-和ω-碘-α，β-不饱和酯。化学选择性随溶剂系统的选择，卤素原子的身份，所用酯的类型，双键的几何形状以及底物的氧化方式而有很大不同。SmI 2介导的反应的立体选择性也受反应参数的影响。

  DOI：

  10.1016/s0040-4020(98)00191-4

文献信息

• Titanocene(III) mediated reduction of organic halides under photoirradiation conditions
  作者：Grégory Hersant、Mounira Bent Sadok Ferjani、Sharon M. Bennett

  DOI：10.1016/j.tetlet.2004.08.119

  日期：2004.10

  Photoirradiation of reaction mixtures, with a xenon lamp in the UV–vis domain, facilitates the titanocene(III) mediated reduction of some organic halides. The substrates studied include ω-halo-α,β-unsaturated esters and a 6-iodohexose derivative.

  用氙灯在UV-vis域中对反应混合物进行光辐照，有助于钛茂（III）介导的某些有机卤化物的还原。研究的底物包括ω-卤代-α，β-不饱和酯和6-碘己糖衍生物。
• Influence of Various Promoters on the Diastereoselectivity of Samarium(II) Iodide Mediated Reductive Carbocyclizations of ω-Iodo-α,β-unsaturated Esters Prepared from 2-Deoxy-d-ribose
  作者：Bita Samim Firouz Salari、Raphinos Kouya Biboutou、Sharon M Bennett

  DOI：10.1016/s0040-4020(00)00583-4

  日期：2000.8

  omega-Iodo-alpha,beta-unsaturated esters were reduced with SmI2 or Bu3SnH under different conditions to give carbocyclic compounds in good yield. The stereoselectivity of the SmI2 cyclizations varies with the choice of promoter, the reaction temperature, the identity of the hydroxyl protecting groups and the geometry of the double bond. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Studies on the diastereoselectivity of samarium(II) iodide mediated reductive carbocyclizations of ω-iodo-α,β-unsaturated esters prepared from 2-deoxy-d-ribose
  作者：Sharon M. Bennett、Raphinos Kouya Biboutou、Bita Samim Firouz Salari

  DOI：10.1016/s0040-4039(98)01552-4

  日期：1998.9

  The title compounds were reduced with SmI2 or Bu3SnH to give carbocyclic compounds in good yield. The stereoselectivity of the SmI2 reductive carbocyclizations varies with the reaction conditions, the double bond geometry and with the identity of the hydroxyl protecting groups. Keywords: Alkenyl halides, carbohydrates, cyclisation, samarium and compounds.
• Studies on the chemoselectivity and diastereoselectivity of samarium(II) iodide mediated transformations of carbohydrate derived ω-halo-α,β-unsaturated esters
  作者：Sharon M. Bennett、Raphinos Kouya Biboutou、Zhihong Zhou、Robert Pion

  DOI：10.1016/s0040-4020(98)00191-4

  日期：1998.5

  Some carbohydrate derived ω-bromo- and ω-iodo- α,β- unsaturated esters were reduced with SmI2 under a variety of conditions. The chemoselectivity varies dramatically with the choice of solvent system, the identity of halogen atom, the type of ester used, the geometry of the double bond, and the oxygenation pattern of the substrate. The stereoselectivity of the SmI2 mediated reactions is also influenced

  在各种条件下，SmI 2还原了一些碳水化合物衍生的ω-溴-和ω-碘-α，β-不饱和酯。化学选择性随溶剂系统的选择，卤素原子的身份，所用酯的类型，双键的几何形状以及底物的氧化方式而有很大不同。SmI 2介导的反应的立体选择性也受反应参数的影响。
• Synthesis of vinylcyclopentanes via samarium(II) mediated tandem reactions
  作者：Mounira Bent Sadok Ferjani、Zhihong Zhou、Sharon M. Bennett

  DOI：10.1016/j.tet.2004.06.099

  日期：2004.9

  In the presence of either visible light or HMPA, SMI2 reacts with some carbohydrate derived w-iodoallylic alcohols, and their acetylated derivatives, to give vinylcyclopentanediol and vinylcyclopentanetriol derivatives. (C) 2004 Elsevier Ltd. All rights reserved.