(3aR,5R,6R,6aR)-6-(4-methoxybenzyloxy)-2,2-dimethyl-5-vinyltetrahydrofuro[2,3-d][1,3]dioxole | 205934-53-8

• 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: (3aR,5R,6R,6aR)-6-(4-methoxybenzyloxy)-2,2-dimethyl-5-vinyltetrahydrofuro[2,3-d][1,3]dioxole
• 英文别名: (3aR,5R,6R,6aR)-5-ethenyl-6-[(4-methoxyphenyl)methoxy]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole
• CAS: 205934-53-8
• 化学式: C₁₇H₂₂O₅
• 分子量: 306.359
• InChiKey: UEJRWVJKYXMCCI-KLHDSHLOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3aR,5R,6R,6aR)-6-(4-methoxybenzyloxy)-2,2-dimethyl-5-vinyltetrahydrofuro[2,3-d][1,3]dioxole 在 盐酸 作用下， 以 甲醇 为溶剂， 以79%的产率得到(3R,4S,5R)-2-Methoxy-4-(4-methoxy-benzyloxy)-5-vinyl-tetrahydro-furan-3-ol
  参考文献：
  名称：

  From Common Carbohydrates to Enantiopure Cyclooctane Polyols and Glycomimetics via Deoxygenative Zirconocene Ring Contraction

  摘要：

  D-Arabinose and D-glucose are transformed into the identical vinyl furanoside, whose role is to serve as the precursor to enantiopure cyclooctadienone 6. The key steps of this relay involve a zirconocene-promoted ring contraction and [3,3] sigmatropic rearrangement of an enynol. Subsequently defined are convenient synthetic routes to several cyclooctane-1,2,3-triols, 1,2,3,4,5-pentaols, and structurally related glycomimetics.

  DOI：

  10.1021/jo051989g
• 作为产物：
  描述：

  1,2:5,6-二异亚丙基-alpha-D-异呋喃糖 在 吡啶 、 盐酸 、 sodium hydride 、 sodium iodide 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 51.0h， 生成 (3aR,5R,6R,6aR)-6-(4-methoxybenzyloxy)-2,2-dimethyl-5-vinyltetrahydrofuro[2,3-d][1,3]dioxole
  参考文献：
  名称：

  锆茂介导的对映体纯的9-氧杂双环壬烷在两个碳桥上均功能化的途径。

  摘要：

  [反应：见正文]由d-阿拉伯糖或d-葡萄糖产生的锆茂介导的4-乙烯基呋喃糖苷的环收缩，随后依次氧化为酮和炔基格氏试剂。所得的顺式-环丁二醇依次进行热重排和分子内的氧合-脱汞。最终闭环的区域化学由R的性质控制。

  DOI：

  10.1021/ol027336t

文献信息

• Total Synthesis of Macrosphelide M from Diacetone Glucose
  作者：Gangavaram V. M. Sharma、Post Sai Reddy

  DOI：10.1002/ejoc.201101603

  日期：2012.4

  The total synthesis of macrosphelide M is described. The key steps include the preparation of the acid and alcohol fragments from diacetone glucose and (S)-malic acid, respectively, followed by Yamaguchi esterification and macrocyclization of the tris-olefin by ring-closing metathesis. Finally, one-pot deprotection of the PMB and TBS groups with TiCl4 results in the target. The C-3/C-4 stereocenters

  描述了 macrosphelide M 的全合成。关键步骤包括分别从双丙酮葡萄糖和 (S)-苹果酸制备酸和醇片段，然后通过闭环复分解对三烯烃进行山口酯化和大环化。最后，用 TiCl4 对 PMB 和 TBS 基团进行一锅法脱保护，得到目标。双丙酮葡萄糖的 C-3/C-4 立体中心用于引入四个立体中心，而第五个立体中心由 (S)-苹果酸实现。
• Studies on the Synthesis of the <i>C</i>-Glycosidic Part of Nogalamycin, Part 2
  作者：Karsten Krohn、Ulrich Flörke、Jürgen Keine、Ina Terstiege

  DOI：10.1080/07328309808002321

  日期：1998.3.1

  The stereochemistry of the addition of metalloaryls 11w-z to the methyl ketones 10a-e was studied in connection with the construction of the hogalamycin C-glycoside. Excellent selectivities towards the (S)-isomer 13a were observed in the beta-chelate model B in the reaction of the benzyl ethers 10a with the cerium reagent 11y and the titanium reagent 11z or the alcohol 10c with the lithium compound 11w. A moderate 3:1 selectivity in favor of the desired (R)-isomer was observed in the reaction of the silyl ether 10d with 11w. A reversal of the addition sequence (reaction of 15a with MeMgI) led exclusively to 13a whereas the alcohol 15c gave a 5:3 mixture of 12c:13c.
• From Common Carbohydrates to Enantiopure Cyclooctane Polyols and Glycomimetics via Deoxygenative Zirconocene Ring Contraction
  作者：Leo A. Paquette、Yunlong Zhang

  DOI：10.1021/jo051989g

  日期：2006.6.1

  D-Arabinose and D-glucose are transformed into the identical vinyl furanoside, whose role is to serve as the precursor to enantiopure cyclooctadienone 6. The key steps of this relay involve a zirconocene-promoted ring contraction and [3,3] sigmatropic rearrangement of an enynol. Subsequently defined are convenient synthetic routes to several cyclooctane-1,2,3-triols, 1,2,3,4,5-pentaols, and structurally related glycomimetics.
• Zirconocene-Mediated Route to Enantiopure 9-Oxabicyclononanes Functionalized on Both Carbon Bridges
  作者：Leo A. Paquette、In Ho Kim、Nicolas Cunière

  DOI：10.1021/ol027336t

  日期：2003.1.1

  see text] A zirconocene-mediated ring contraction of 4-vinylfuranosides generated either from d-arabinose or d-glucose is followed by sequential oxidation to the ketone and alkynyl Grignard addition. The resulting cis-cyclobutanediols are subjected in turn to thermal rearrangement and intramolecular oxymercuration-demercuration. The regiochemistry of the final ring closure is controlled by the nature

  [反应：见正文]由d-阿拉伯糖或d-葡萄糖产生的锆茂介导的4-乙烯基呋喃糖苷的环收缩，随后依次氧化为酮和炔基格氏试剂。所得的顺式-环丁二醇依次进行热重排和分子内的氧合-脱汞。最终闭环的区域化学由R的性质控制。