(S)-1-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-but-3-en-1-ol | 106220-96-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-1-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-but-3-en-1-ol
• 英文别名: (1S)-1-[(3aR,5R,6S,6aR)-2,2-dimethyl-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]but-3-en-1-ol
• CAS: 106220-96-6
• 化学式: C₁₈H₂₄O₅
• 分子量: 320.386
• InChiKey: OXNGWRXHJFTTAE-DMRKSPOLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-1-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-but-3-en-1-ol 在 咪唑 、 iodonium(di-γ-collidine) perchlorate 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.17h， 生成 (R)-5-{(S)-Benzyloxy-[(2S,3R)-3-(tert-butyl-dimethyl-silanyloxy)-5-iodomethyl-tetrahydro-furan-2-yl]-methyl}-2,2-dimethyl-[1,3]dioxolan-4-ol
  参考文献：
  名称：

  1,2-O-Isopropylidenefuranose Templates for the Synthesis of Complex Cyclic Ethers via Neighboring Group Participation by the Acetal Ring Oxygen

  摘要：

  Novel strategies are described for the direct transformation of C5-allylated-1,2-O-isopropylidene-furanoses into complex cyclic ethers. Reaction of these substrates with iodonium ion under aqueous conditions resulted in the facile formation of 2,5-disubstituted tetrahydrofurans (THF's) containing highly substituted branches, in good to high yields, albeit with modest cis stereoselectivity. A similar result was obtained for the one case of the analogous tetrahydropyran (THP) system that was examined. These reactions presumably proceed via neighboring group participation by the acetal ring oxygen on an iodonium ion-alkene charge transfer complex to give a cyclic oxonium ion, thence a cyclic ether-oxocarbenium ion which undergoes intermolecular capture by water. Under anhydrous conditions, substrates which contained a 3-0-(2'-methyl-2'-buten-4'-yl) substituent led to high yields of adjacently connected THF-THP or THP-THP structures. These products are explainable in terms of a two-step process in which a cyclic ether-oxocarbenium ion, resulting from the initial participation reaction, undergoes nucleophilic capture by the activated alkene. A notable feature of this reaction was that only a single THP isomer was obtained in the second ring forming reaction, presumably a consequence of the cyclic nature of the oxocarbenium ion derived from the 1,2-O-isopropylidene acetal residue.

  DOI：

  10.1021/jo00105a012
• 作为产物：
  描述：

  3-O-苄基-1,2-O-异亚丙基-Alpha-D-木质二醛糖 、 烯丙基三甲基硅烷 在 四氯化钛 作用下， 以74%的产率得到(S)-1-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-but-3-en-1-ol
  参考文献：
  名称：

  On the communication of chirality from furanose and pyranose rings to monosaccharide side chains: anomalous results in the glucose series

  摘要：

  DOI：

  10.1016/s0040-4020(01)90570-8

文献信息

• Chelation controlled addition of allylstannanes to aldehydes in lithium perchlorate-diethyl ether
  作者：Kenneth J. Henry、Paul A. Grieco、Christopher T. Jagoe

  DOI：10.1016/s0040-4039(00)74150-5

  日期：1992.3

  α-Alkoxy aldehydes undergo chelation controlled addition of allylstannanes with high diastereoselectivity in the presence of 5.0 M lithium perchlorate in diethyl ether at ambient temperature and pressure.

  在环境温度和压力下，在乙醚中有5.0 M高氯酸锂存在下，α-烷氧基醛具有螯合控制的高非对映选择性的烯丙基锡烷酸加成反应。
• Ytterbium trifluoromethanesulfonate [Yb(OTf)3] promoted indium mediated allylation reactions of carbonyl compounds in aqueous media
  作者：Ruibin Wang、Chong-Meng Lim、Choon-Hong Tan、Bee-Khim Lim、Keng-Yeow Sim、Teck-Peng Loh

  DOI：10.1016/0957-4166(95)00228-h

  日期：1995.8

  Indium-mediated allylation reactions of the sugar derivative 1 in aqueous media have been found to proceed with high anti diastereofacial selectivity in the presence of ytterbium trifluoromethanesulfonate as Lewis acid.
• On the communication of chirality from furanose and pyranose rings to monosaccharide side chains: anomalous results in the glucose series
  作者：Samuel J. danishefsky、Michael P. DeNinno、Gary B. Phillips、Robert E. Zelle、Paul A. Lartey

  DOI：10.1016/s0040-4020(01)90570-8

  日期：1986.1
• 1,2-O-Isopropylidenefuranose Templates for the Synthesis of Complex Cyclic Ethers via Neighboring Group Participation by the Acetal Ring Oxygen
  作者：Weifang Shan、Phyllis Wilson、Wei Liang、David R. Mootoo

  DOI：10.1021/jo00105a012

  日期：1994.12

  Novel strategies are described for the direct transformation of C5-allylated-1,2-O-isopropylidene-furanoses into complex cyclic ethers. Reaction of these substrates with iodonium ion under aqueous conditions resulted in the facile formation of 2,5-disubstituted tetrahydrofurans (THF's) containing highly substituted branches, in good to high yields, albeit with modest cis stereoselectivity. A similar result was obtained for the one case of the analogous tetrahydropyran (THP) system that was examined. These reactions presumably proceed via neighboring group participation by the acetal ring oxygen on an iodonium ion-alkene charge transfer complex to give a cyclic oxonium ion, thence a cyclic ether-oxocarbenium ion which undergoes intermolecular capture by water. Under anhydrous conditions, substrates which contained a 3-0-(2'-methyl-2'-buten-4'-yl) substituent led to high yields of adjacently connected THF-THP or THP-THP structures. These products are explainable in terms of a two-step process in which a cyclic ether-oxocarbenium ion, resulting from the initial participation reaction, undergoes nucleophilic capture by the activated alkene. A notable feature of this reaction was that only a single THP isomer was obtained in the second ring forming reaction, presumably a consequence of the cyclic nature of the oxocarbenium ion derived from the 1,2-O-isopropylidene acetal residue.