(2S)-1-O-trityl-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-4-pentene-1,2-diol | 208168-09-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: (2S)-1-O-trityl-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-4-pentene-1,2-diol
• 英文别名: (2S)-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-trityloxypent-4-en-2-ol
• CAS: 208168-09-6
• 化学式: C₂₉H₃₂O₄
• 分子量: 444.571
• InChiKey: IWIFUVKKMJMIRM-XCZPVHLTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S)-1-O-trityl-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-4-pentene-1,2-diol 在 三乙胺 、 三氟乙酸 、 三氟乙酸酐 作用下， 以 二氯甲烷 为溶剂， 以80%的产率得到(2S)-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-4-pentene-1,2-diol
  参考文献：
  名称：

  Stereoselective allylations of erythrulose derivatives under anhydrous conditions

  摘要：

  We have investigated a number of nucleophilic additions or allylating reagents to several alpha,alpha ',beta -trioxygenated ketones (O-protected erythrulose derivatives), Reagents based on lithium. magnesium. copper and titanium stereoselectivities and did not display any recognizable trend in the sense of stereoselection. In contrast, reactions involving silicon and tin derivatives were highly stereoselective and gage rise to essentially a single diastereoisomer, the structure of which depended group. Thus, alpha,beta -di-O-benzylated derivatives experienced almost exclusive addition to the carbonyl Si on the type or protecting group side, whereas alpha,beta -O,O-alkylidene derivatives (dioxolane acetals) yielded the opposite diastereoisomers as a result of addition to the Re side. These results Suggest the intermediacy of a-chelates in the additions or silicon and tin reagents to the di-O-benzylated derivatives. In contrast, the opposite stereoisomers. formed in the reactions of dioxolanes. are believed to be formed through Felkin-Anh transition states, pointing to the reluctance of acetal ox gens to participate in chelated intermediates. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(01)00262-2
• 作为产物：
  描述：

  烯丙基三丁基锡 、 3,4-O-isopropylidene-1-O-triphenylmethyl-L-glycero-2-tetrulose 在 4 A molecular sieve 、 magnesium bromide 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以85%的产率得到(2S)-1-O-trityl-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-4-pentene-1,2-diol
  参考文献：
  名称：

  Stereoselective allylations of erythrulose derivatives under anhydrous conditions

  摘要：

  We have investigated a number of nucleophilic additions or allylating reagents to several alpha,alpha ',beta -trioxygenated ketones (O-protected erythrulose derivatives), Reagents based on lithium. magnesium. copper and titanium stereoselectivities and did not display any recognizable trend in the sense of stereoselection. In contrast, reactions involving silicon and tin derivatives were highly stereoselective and gage rise to essentially a single diastereoisomer, the structure of which depended group. Thus, alpha,beta -di-O-benzylated derivatives experienced almost exclusive addition to the carbonyl Si on the type or protecting group side, whereas alpha,beta -O,O-alkylidene derivatives (dioxolane acetals) yielded the opposite diastereoisomers as a result of addition to the Re side. These results Suggest the intermediacy of a-chelates in the additions or silicon and tin reagents to the di-O-benzylated derivatives. In contrast, the opposite stereoisomers. formed in the reactions of dioxolanes. are believed to be formed through Felkin-Anh transition states, pointing to the reluctance of acetal ox gens to participate in chelated intermediates. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(01)00262-2

文献信息

• Synthesis of conjugated γ- and δ-lactones from aldehydes and ketones via a vinylation(allylation)-ring closing metathesis–oxidation sequence
  作者：J.Alberto Marco、Miguel Carda、Santiago Rodrı́guez、Encarnación Castillo、Marı́a N. Kneeteman

  DOI：10.1016/s0040-4020(03)00584-2

  日期：2003.6

  aldehydes and ketones followed by O-allylation of the obtained carbinols gave the corresponding allyl or homoallyl ethers, respectively. Ring-closing metathesis of these compounds afforded in many cases cyclic ethers (dihydrofurans and dihydropyrans, respectively) bearing disubstituted and trisubstituted CC bonds. These were then subjected to allylic oxidation to yield conjugated γ- and δ-lactones. Reasons

  醛和酮的亲核C-乙烯基化和C-烯丙基化，然后将得到的甲醇进行O-烯丙基化，分别得到相应的烯丙基或高烯丙基醚。这些化合物的闭环易位在许多情况下提供带有二取代和三取代的CC键的环状醚（分别为二氢呋喃和二氢吡喃）。然后将它们进行烯丙基氧化以产生共轭的γ-和δ-内酯。介绍并讨论了观察到的故障的原因。
• Synthesis of Conjugated γ- and δ-Lactones from Aldehydes and Ketones via a Vinylation/Allylation-Ring Closing Metathesis-Oxidation Sequence
  作者：Miguel Carda、Encarnación Castillo、Santiago Rodríguez、Santiago Uriel、J. Alberto Marco

  DOI：10.1055/s-1999-2897

  日期：——

  Nucleophilic C-vinylation or C-allylation of aldehydes and ketones followed by O-allylation of the obtained carbinols gave the corresponding allyl ethers. Ring-closing metathesis of the latter afforded cyclic ethers (dihydrofurans and dihydropyrans, respectively) which were then subjected to allylic oxidation to yield conjugated γ- and δ-lactones.

  通过对醛和酮进行亲核碳乙烯基化或碳烯丙基化反应，随后对所得卡宾醇进行氧烯丙基化，得到了相应的烯丙醚。后者经过环闭合易位反应，分别得到环醚（二氢呋喃和二氢吡喃），再经过烯丙位的氧化反应，分别生成共轭的γ-和δ-内酯。
• Stereoselective indium-mediated allylation of erythrulose derivatives in aqueous media
  作者：M Carda、E Castillo、S Rodrı́guez、J Murga、J.A Marco

  DOI：10.1016/s0957-4166(98)00103-7

  日期：1998.4

  A range of erythrulose derivatives has been allowed to react with allyl bromide and metallic indium in THF or aqueous THE Some of these allylations are highly stereoselective. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.