[(2R,3S)-3-acetyloxy-6-prop-2-enyl-3,6-dihydro-2H-pyran-2-yl]methyl acetate | 1135521-22-0

• 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)-3-acetyloxy-6-prop-2-enyl-3,6-dihydro-2H-pyran-2-yl]methyl acetate
• CAS: 1135521-22-0
• 化学式: C₁₃H₁₈O₅
• 分子量: 254.283
• InChiKey: MPRBSSKQJFGMFR-LWNNLKQOSA-N

物化性质

• 沸点：
  324.0±42.0 °C(predicted)
• 密度：
  1.11±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [(2R,3S)-3-acetyloxy-6-prop-2-enyl-3,6-dihydro-2H-pyran-2-yl]methyl acetate 在 D(+)-10-樟脑磺酸 、 三乙胺 作用下， 以 甲醇 、 水 、 1,2-二氯乙烷 为溶剂， 生成 3-(4,6-O-benzylidene-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl)-1-propene
  参考文献：
  名称：

  Synthetic studies toward marine toxic polyethers (2) synthesis of the B-segment of okadaic acid and coupling with the C-segment

  摘要：

  DOI：

  10.1016/s0040-4039(01)91116-5
• 作为产物：
  描述：

  烯丙基三甲基硅烷 、 乙酰化葡萄烯糖 在 氯化锆(IV) 作用下， 以 乙腈 为溶剂， 反应 0.05h， 以94%的产率得到[(2R,3S)-3-acetyloxy-6-prop-2-enyl-3,6-dihydro-2H-pyran-2-yl]methyl acetate
  参考文献：
  名称：

  ZrCl₄-Catalyzed Efficient Ferrier Glycosylation: A Facile Synthesis of Pseudoglycals

  摘要：

  三-O-乙酰基-d-葡糖醛与硅烷亲核试剂、醇和硫醇的反应在少量四氯化锆的催化作用下有效促进，生成相应的伪葡糖醛，经过Ferrier重排反应。

  DOI：

  10.1055/s-2004-815974

文献信息

• In(OTf)₃—A New Efficient Lewis Acid Catalyst for Stereoselective C-Glycosylation Reactions of Glycal Derivatives
  作者：Rina Ghosh、Arijit Chakraborty、Dilip K. Maiti

  DOI：10.1081/scc-120018923

  日期：2003.1.6

  A variety of glycal derivatives reacted smoothly with allyltrimethylsilane and trimethylsilylcyanide in neat condition as well as in dichloromethane in the presence of 2-5 mol% of In(OTf)(3) affording the corresponding 2,3-unsaturated C-glycosides in excellent yields and moderate to excellent alpha-selectivities.
• Synthesis of 2,3-unsaturated C-glycosides by HClO4–SiO2 catalyzed Ferrier rearrangement of glycals
  作者：Pallavi Tiwari、Geetanjali Agnihotri、Anup Kumar Misra

  DOI：10.1016/j.carres.2004.12.022

  日期：2005.3

  Alkyl 2,3-unsaturated C-glycopyranosides have been prepared by Ferrier rearrangement of acyl or alkyl protected glycals catalyzed by HClO4-SiO2. (c) 2005 Elsevier Ltd. All rights reserved.
• Mild and Highly Efficient Stereoselective Synthesis of 2,3‐Unsaturated Glycopyranosides using La(NO₃)₃ · 6H₂O as a Catalyst: Ferrier Rearrangement
  作者：N. Suryakiran、S. Malla Reddy、M. Srinivasulu、Y. Venkateswarlu

  DOI：10.1080/00397910701744170

  日期：2008.1

  A mild and highly efficient stereoselective reaction of 3,4,6-tri-O-acetyl-D-glucal with a variety of nucleophiles, viz. alcohols, phenols, thiols, thiophenols, and allyl trimethyl silane (TMS), in the presence of 5 mol% of lanthanum(III) nitrate hexahydrate under solvent-free conditions yielded the corresponding 2,3-unsaturated glycopyranosides (pseudoglycals) in excellent yields.
• ICHIKAWA, YOSHIYASU;ISOBE, MINORU;GOTO, TOSHIO, TETRAHEDRON, 43,(1987) N 20, 4749-4758
  作者：ICHIKAWA, YOSHIYASU、ISOBE, MINORU、GOTO, TOSHIO

  DOI：——

  日期：——