(2S)-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-4-pentene-1,2-diol | 208168-07-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S)-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]pent-4-ene-1,2-diol
• CAS: 208168-07-4
• 化学式: C₁₀H₁₈O₄
• 分子量: 202.251
• InChiKey: JSOBJSWRPFOLJV-WPRPVWTQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S)-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-4-pentene-1,2-diol 在 palladium on activated charcoal 3,5-二甲基吡唑 、 chromium(VI) oxide 、 lead(IV) acetate 、 sodium hydroxide 、 copper(l) iodide 、 Grubbs catalyst first generation 、 氢气 、 四丁基硫酸氢铵 、 四丁基碘化铵 、 potassium hydride 、 L-Selectride 、 二正丁基氧化锡 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 77.83h， 生成 (+)-tanikolide
  参考文献：
  名称：

  使用闭环易位立体选择性合成（-）-麦芽灵，（+）-麦芽灵和（+）-tanikolide

  摘要：

  描述了天然存在的δ-内酯（+）-tanikolide和（-）-malyngolide以及后者的非天然（+）-对映异构体的立体选择性合成。这些合成中的每个关键步骤是将有机金属试剂立体选择性地添加到α-氧化的酮和烯烃闭环复分解反应中。

  DOI：

  10.1016/s0040-4020(02)01594-6
• 作为产物：
  描述：

  (2S)-1-O-(tert-butyldiphenylsilyl)-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-4-pentene-1,2-diol 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以84%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：

  通过闭环烯烃复分解的立体选择性合成（+）-麦芽寡糖

  摘要：

  描述了由1-赤藓糖非常短和立体选择性地合成麦芽糖内酯的非天然对映体。合成的关键特征是聚氧酮的Felkin-Anh非对映选择性烯丙基化和我们小组最近描述的烯丙基化/复分解/烯丙基氧化方案。

  DOI：

  10.1016/s0040-4039(00)00884-4

文献信息

• A stereoselective synthesis of (+)-malyngolide via a ring-closing olefin metathesis
  作者：Miguel Carda、Encarnación Castillo、Santiago Rodrı́guez、J.Alberto Marco

  DOI：10.1016/s0040-4039(00)00884-4

  日期：2000.7

  A very short and stereoselective synthesis of the non-natural enantiomer of malyngolide from l-erythrulose is described. Key features of the synthesis are the Felkin–Anh diastereoselective allylation of a polyoxygenated ketone and the allylation/metathesis/allylic oxidation protocol recently described by our group.

  描述了由1-赤藓糖非常短和立体选择性地合成麦芽糖内酯的非天然对映体。合成的关键特征是聚氧酮的Felkin-Anh非对映选择性烯丙基化和我们小组最近描述的烯丙基化/复分解/烯丙基氧化方案。
• 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.
• Stereoselective allylations of erythrulose derivatives under anhydrous conditions
  作者：Miguel Carda、Encarna Castillo、Santiago Rodrı́guez、Florenci González、J.Alberto Marco

  DOI：10.1016/s0957-4166(01)00262-2

  日期：2001.6

  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.
• Stereoselective synthesis of (−)-malyngolide, (+)-malyngolide and (+)-tanikolide using ring-closing metathesis
  作者：Miguel Carda、Santiago Rodrı́guez、Encarnación Castillo、Alejandro Bellido、Santiago Dı́az-Oltra、J Alberto Marco

  DOI：10.1016/s0040-4020(02)01594-6

  日期：2003.2

  The stereoselective syntheses of the naturally occurring δ-lactones (+)-tanikolide and (−)-malyngolide as well as of the unnatural (+)-enantiomer of the latter are described. Key steps in each of these syntheses were stereoselective additions of organometallic reagents to α-oxygenated ketones and olefin ring-closing metatheses.

  描述了天然存在的δ-内酯（+）-tanikolide和（-）-malyngolide以及后者的非天然（+）-对映异构体的立体选择性合成。这些合成中的每个关键步骤是将有机金属试剂立体选择性地添加到α-氧化的酮和烯烃闭环复分解反应中。