(4R,5R)-4-(2,2-dibromovinyl)-2,2,5-trimethyl-1,3-dioxolane | 163161-10-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4R,5R)-4-(2,2-dibromovinyl)-2,2,5-trimethyl-1,3-dioxolane
• 英文别名: (4R,5R)-4-(2,2-dibromoethenyl)-2,2,5-trimethyl-1,3-dioxolane
• CAS: 163161-10-2
• 化学式: C₈H₁₂Br₂O₂
• 分子量: 299.99
• InChiKey: UBLBHRPAMIUMCC-PHDIDXHHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4R,5R)-4-(2,2-dibromovinyl)-2,2,5-trimethyl-1,3-dioxolane 在 喹啉 、 正丁基锂 、 2,2,6,6-四甲基哌啶氧化物 、 碘苯二乙酸 、 四丁基氟化铵 、 氢气 、 (-)-CSA 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 13.25h， 生成 (S)-5-((4R,5R, Z)-4, 5-dihydroxyhex-2-enyl)dihydrofuran-2(3H)-one
  参考文献：
  名称：

  甾烷内酯G修饰结构的立体选择性合成

  摘要：

  通过11个步骤就可以精确地合成甾烷内酯G的修饰结构，总产率为31.7％。关键的反应序列包括BAIB / TEMPO介导的串联氧化和内酯化，Lindlar的氢化反应，通过原位生成的作为亲核试剂的炔基的区域选择性环氧化物打开，Sharpless不对称二羟基化反应和Jacobsen动力学拆分。

  DOI：

  10.1016/j.tetlet.2013.11.071
• 作为产物：
  描述：

  (4R,5R)-5-hydroxymethyl-2,2,4-trimethyl-1,3-dioxolane 在 草酰氯 、 二甲基亚砜 、 三乙胺 、 三苯基膦 作用下， 反应 0.83h， 生成 (4R,5R)-4-(2,2-dibromovinyl)-2,2,5-trimethyl-1,3-dioxolane
  参考文献：
  名称：

  Approach towards C12 oxo analogues of the side chain of pumiliotoxin B/allopumiliotoxin 339A and B

  摘要：

  A route towards the synthesis of analogues of pumiliotoxin and allopumiliotoxin side-chain is described. The C I 5,C 16 diol was introduced by asymmetric dihydroxylation using AD-mix beta of C10,C17 enynone intermediate 14, or of C13,C17 precursor 17, or by using a chiron-based route from 24. The trisubstituted alkene functionality was established using arylthio conjugate addition to ynones 16 and 27, followed by a copper-catalyzed stereoretentive reaction with methylmagnesium bromide. The approach enables access to C12 oxo systems and offers an approach towards new C14 analogues. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01071-7

文献信息

• Syntheses of specifically labelled 2,3,6-trideoxyhexoses
  作者：Andreas Kirschning、Ulrike Hary、Monika Ries

  DOI：10.1016/0040-4020(94)01081-a

  日期：1995.2

  Two synthetic approaches producing L-(-) and D-(+)-rhodinose (6 and 13 respectively), L-(-)-(19)- and D-(+)- amicetose and L- and D-enopyranose 15 specifically deuterated at C-2 and C-3 are described. The strategy which starts from threonine also offers the opportunity for the synthesis of the [I-C-13]-labelled compounds.
• Approach towards C12 oxo analogues of the side chain of pumiliotoxin B/allopumiliotoxin 339A and B
  作者：John M. Gardiner、Philip E. Giles、Marı́a Luz Martı́n Martı́n

  DOI：10.1016/s0040-4039(02)01071-7

  日期：2002.7

  A route towards the synthesis of analogues of pumiliotoxin and allopumiliotoxin side-chain is described. The C I 5,C 16 diol was introduced by asymmetric dihydroxylation using AD-mix beta of C10,C17 enynone intermediate 14, or of C13,C17 precursor 17, or by using a chiron-based route from 24. The trisubstituted alkene functionality was established using arylthio conjugate addition to ynones 16 and 27, followed by a copper-catalyzed stereoretentive reaction with methylmagnesium bromide. The approach enables access to C12 oxo systems and offers an approach towards new C14 analogues. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Stereoselective synthesis of revised structure of stagonolide G
  作者：K. Rajendra Prasad、A. Venkanna、K. Suresh Babu、A.R. Prasad、J. Madhusudana Rao

  DOI：10.1016/j.tetlet.2013.11.071

  日期：2014.1

  A concise total synthesis of the revised structure of stagonolide G has been achieved in 11 steps and with an overall yield of 31.7%. Key reaction sequence includes BAIB/TEMPO mediated tandem oxidation and lactonization, Lindlar’s hydrogenation, regioselective epoxide opening by an in situ generated alkynyl as nucleophile, Sharpless asymmetric dihydroxylation, and Jacobsen kinetic resolution.

  通过11个步骤就可以精确地合成甾烷内酯G的修饰结构，总产率为31.7％。关键的反应序列包括BAIB / TEMPO介导的串联氧化和内酯化，Lindlar的氢化反应，通过原位生成的作为亲核试剂的炔基的区域选择性环氧化物打开，Sharpless不对称二羟基化反应和Jacobsen动力学拆分。