ethyl 2-bromo-2-[6-[2,2-dimethyl-(4R)-1,3-dioxolan-4-yl]-4-(4-hydroxy-2-butynyloxy)-2,2-dimethyl-(3aS,4S,6R,6aS)-perhydrofuro[3,4-d][1,3]dioxol-4-yl]acetate | 273731-24-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2-bromo-2-[6-[2,2-dimethyl-(4R)-1,3-dioxolan-4-yl]-4-(4-hydroxy-2-butynyloxy)-2,2-dimethyl-(3aS,4S,6R,6aS)-perhydrofuro[3,4-d][1,3]dioxol-4-yl]acetate
• 英文别名: ethyl 2-[(3aS,4S,6R,6aS)-6-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-4-(4-hydroxybut-2-ynoxy)-2,2-dimethyl-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxol-4-yl]-2-bromoacetate
• CAS: 273731-24-1
• 化学式: C₂₀H₂₉BrO₉
• 分子量: 493.349
• InChiKey: PMAANMGUYKBQTQ-YKWQPGCNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  ethyl 2-bromo-2-[6-[2,2-dimethyl-(4R)-1,3-dioxolan-4-yl]-4-(4-hydroxy-2-butynyloxy)-2,2-dimethyl-(3aS,4S,6R,6aS)-perhydrofuro[3,4-d][1,3]dioxol-4-yl]acetate 在 偶氮二异丁腈 、 三丁基氯化锡 、 sodium cyanoborohydride 作用下， 以 叔丁醇 为溶剂， 以79%的产率得到ethyl 6'-[2,2-dimethyl-(4R)-1,3-dioxolan-4-yl]-4-[2-hydroxy-(Z)-ethylidene]-2',2'-dimethyl-(2'R,3R,3a'S,6'R,6a'S)-spiro[3H,4H,5H-furan-2,4'-perhydrofuro[3,4-d][1,3]dioxole]-3-carboxylate
  参考文献：
  名称：

  Radical reactions on enol-esters: facile synthesis of 3-ulosonic acid derivatives and chiral spiroacetals

  摘要：

  A two-step approach to 3-ulosonic acid derivatives and chiral spiroacetals from enol-esters is presented. The strategy involves 1.4-addition of a variety of alcohols onto enol-esters in the presence of NBS to give alpha-bromoacetals, which undergo a regio- and stereoselective radical cyclisation to give the highly functionalised chiral spiroacetals, while debromination gives 3-ulosonic acid derivatives. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00448-8
• 作为产物：
  描述：

  丁炔二醇 、 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 乙腈 为溶剂， 生成 ethyl 2-bromo-2-[6-[2,2-dimethyl-(4R)-1,3-dioxolan-4-yl]-4-(4-hydroxy-2-butynyloxy)-2,2-dimethyl-(3aS,4S,6R,6aS)-perhydrofuro[3,4-d][1,3]dioxol-4-yl]acetate
  参考文献：
  名称：

  自由基介导的烯醇酯手性螺缩醛的立体选择性合成†

  摘要：

  描述了衍生自d-甘露聚糖内酯的从烯醇酯1开始的手性螺缩醛的立体选择性合成。该策略涉及在NBS存在下将各种醇1，4-加成1生成α-溴缩醛，然后进行区域和立体选择性自由基环化，生成高度官能化的手性螺缩醛。

  DOI：

  10.1016/s0040-4039(00)00083-6

文献信息

• Radical mediated stereoselective synthesis of chiral spiroacetals from enol-esters
  作者：G.V.M Sharma、A.Subash Chander、V Goverdhan Reddy、K Krishnudu、M.H.V Ramana Rao、A.C Kunwar

  DOI：10.1016/s0040-4039(00)00083-6

  日期：2000.3

  Stereoselective synthesis of chiral spiroacetals starting from enol-ester 1, derived from d-manno lactone, is described. The strategy involves 1,4-addition of a variety of alcohols to 1 in the presence of NBS to give α-bromo acetals, which undergo a regio- and stereoselective radical cyclisation to give highly functionalised chiral spiroacetals.

  描述了衍生自d-甘露聚糖内酯的从烯醇酯1开始的手性螺缩醛的立体选择性合成。该策略涉及在NBS存在下将各种醇1，4-加成1生成α-溴缩醛，然后进行区域和立体选择性自由基环化，生成高度官能化的手性螺缩醛。
• Radical reactions on enol-esters: facile synthesis of 3-ulosonic acid derivatives and chiral spiroacetals
  作者：G.V.M. Sharma、Rakesh、A.Subhash Chander、V.Goverdhan Reddy、M.H.V.Ramana Rao、A.C. Kunwar

  DOI：10.1016/s0957-4166(03)00448-8

  日期：2003.10

  A two-step approach to 3-ulosonic acid derivatives and chiral spiroacetals from enol-esters is presented. The strategy involves 1.4-addition of a variety of alcohols onto enol-esters in the presence of NBS to give alpha-bromoacetals, which undergo a regio- and stereoselective radical cyclisation to give the highly functionalised chiral spiroacetals, while debromination gives 3-ulosonic acid derivatives. (C) 2003 Elsevier Ltd. All rights reserved.