tert-butyl (2Z)-2,3,4,7-tetradeoxy-7-iodo-5,6-O-(1-methylethylidene)-D-ribo-hept-2-enoate | 214398-21-7

• 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 (2Z)-2,3,4,7-tetradeoxy-7-iodo-5,6-O-(1-methylethylidene)-D-ribo-hept-2-enoate
• 英文别名: tert-butyl (Z)-4-[(4S,5S)-5-(iodomethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]but-2-enoate
• CAS: 214398-21-7
• 化学式: C₁₄H₂₃IO₄
• 分子量: 382.239
• InChiKey: YYAQNVHNKMZPJE-OBCZMHBZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl (2Z)-2,3,4,7-tetradeoxy-7-iodo-5,6-O-(1-methylethylidene)-D-ribo-hept-2-enoate 在 甲醇 、 六甲基磷酰三胺 、 samarium diiodide 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 6.75h， 生成 (3aR,5S,6aS)-2,2-Dimethyl-5-vinyl-tetrahydro-cyclopenta[1,3]dioxole
  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：

  2,2-二甲氧基丙烷 、 tert-butyl (2Z)-2,3,4,7-tetradeoxy-7-iodo-D-ribo-hept-2-enoate 在 对甲苯磺酸 作用下， 生成 tert-butyl (2Z)-2,3,4,7-tetradeoxy-7-iodo-5,6-O-(1-methylethylidene)-D-ribo-hept-2-enoate
  参考文献：
  名称：

  Studies on the diastereoselectivity of samarium(II) iodide mediated reductive carbocyclizations of ω-iodo-α,β-unsaturated esters prepared from 2-deoxy-d-ribose

  摘要：

  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.

  DOI：

  10.1016/s0040-4039(98)01552-4

文献信息

• 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.