(2R,3S,6RS)-3-acetoxy-6-cyclohexyloxy-3,6-dihydro-2H-pyran-2-methanol acetate | 61773-60-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (2R,3S,6RS)-3-acetoxy-6-cyclohexyloxy-3,6-dihydro-2H-pyran-2-methanol acetate
• 英文别名: [(2R,3S)-3-acetyloxy-6-cyclohexyloxy-3,6-dihydro-2H-pyran-2-yl]methyl acetate
• CAS: 61773-60-2
• 化学式: C₁₆H₂₄O₆
• 分子量: 312.363
• InChiKey: PRTOYGXCUGXISF-QMRHZFGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  环己醇 、 乙酰化葡萄烯糖 在 indium(III) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以90%的产率得到(2R,3S,6RS)-3-acetoxy-6-cyclohexyloxy-3,6-dihydro-2H-pyran-2-methanol acetate
  参考文献：
  名称：

  Bi(OTf)3 and SiO2-Bi(OTf)3 as Effective Catalysts for the Ferrier Rearrangement#

  摘要：

  经发现，Bi(OTf)3 和 SiO2-Bi(OTf)3 能有效催化三-O-乙酰基糖类的Ferrier重排反应，在不同的醇作用下，提供了一条有效合成2,3-不饱和O-糖苷的途径，具有良好的异头选择性和良好的至极佳的产率，且反应时间短。

  DOI：

  10.3390/10080884

文献信息

• Use of 2-phenylsulphonyl cyclic ethers in the preparation of tetrahydropyran and tetrahydrofuran acetals and in some glycosidation reactions.
  作者：Dearg S. Brown、Steven V. Ley、Sadie Vile、Mervyn Thompson

  DOI：10.1016/s0040-4020(01)86389-4

  日期：1991.1

  2-Phenylsulphonyl cyclic ethers undergo facile displacement of the sulphonyl group by alcohols, in the presence of magnesium bromide etherate and sodium bicarbonate in tetrahydrofuran, to give goodyields of the corresponding acetals.

  2-苯基磺酰基环醚在四氢呋喃中的溴化镁醚化物和碳酸氢钠存在下，通过醇容易地置换磺酰基，以得到相应的缩醛的良好收率。
• Amberlyst 15–Catalyzed Efficient Synthesis of 2,3‐Unsaturated Glycosides via Ferrier Rearrangement for Glycal
  作者：Qiang Tian、Xing‐Mei Zhu、Jin‐Song Yang

  DOI：10.1080/00397910601131353

  日期：2007.3
• Protic Acid (HClO₄ Supported on Silica Gel)-Mediated Synthesis of 2,3-Unsaturated-<i>O</i>-glucosides and a Chiral Furan Diol from 2,3-Glycals
  作者：Aditi Agarwal、Shikha Rani、Yashwant D. Vankar

  DOI：10.1021/jo049415j

  日期：2004.9.1

  Perchloric acid supported on silica gel acts as an excellent reagent system in converting glucals into 2,3-unsaturated-O-glucosides in good to excellent yields in short reaction time with good a selectivity. Primary, secondary, and allylic alcohols, phenols, and thiols react with 3,4,6-tri-O-acetyl glucal with equal ease. In addition to this, a chiral furan diol is obtained from unprotected D-glucal or D-galactal in good yields.
• Sobhana Babu; Balasubramanian, Synthetic Communications, 1999, vol. 29, # 24, p. 4299 - 4305
  作者：Sobhana Babu、Balasubramanian

  DOI：——

  日期：——
• Reactions of Various Nucleophiles with <scp>d</scp>-Glucal over Keggin-Type Heteropoly Compounds: A Simple, Rapid, and Expedient Method for the Synthesis of Pseudoglycals
  作者：Ezzat Rafiee、Sara Eavani、Mohammad Joshaghani

  DOI：10.1080/07328300903477796

  日期：2010.1.14

  The reaction of benzyl alcohol with 3,4,6-tri-O-acetyl-d-glucal has been investigated with several heteropoly compounds, and the optimal catalyst is 12-tungstophosphoric acid supported on carbon. In the presence of this catalyst, various alcohols gave the corresponding alkyl and aryl 2,3-unsaturated glycopyranosides in excellent yields and good anomeric selectivity under solvent-free condition. 4,6-Di-O-acetyl-2,3-dideoxy--d-erythro-hex-2-enopyranosyl cyanide and ethyl 4,6-di-O-acetyl-2,3-dideoxy-1-thio--d-erythro-hex-2-enopyranoside have also been prepared with trimethylsilyl cyanide and ethanthiol as nucleophiles, respectively. The catalyst could be easily recovered and reused several times with slight loss of activity. The selectivity to give -anomers predominantly did not show any change in all runs.