Acetic acid (2S,3R,6S)-6-isopropoxy-2-methyl-3,6-dihydro-2H-pyran-3-yl ester | 101665-42-3

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: Acetic acid (2S,3R,6S)-6-isopropoxy-2-methyl-3,6-dihydro-2H-pyran-3-yl ester
• 英文别名: (1'-methyl-ethyl) 4-O-acetyl-2,3,6-trideoxy-α-L-erythro-hex-2-enopyranoside
• CAS: 101665-42-3；101665-39-8
• 化学式: C₁₁H₁₈O₄
• 分子量: 214.262
• InChiKey: GNICOSFGLCYSEQ-JMJZKYOTSA-N

物化性质

• 沸点：
  270.6±40.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.64
• 重原子数：
  15.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (2S,3R,6S)-6-isopropoxy-2-methyl-3,6-dihydro-2H-pyran-3-yl ester 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 16.0h， 以98%的产率得到(1'-methyl-ethyl) 2,3,6-trideoxy-α-L-erythro-hex-2-enopyranoside
  参考文献：
  名称：

  Synthesis and Raman spectra of 3-deoxy-α-l-rhamnosides as model sugars of the Ascaris egg shell

  摘要：

  The synthesis of two 3-deoxy-alpha-L-rhamnosides (i.e., 3,6-dideoxy-L-arabino-hexopyranosides) as models of ascaroside natural products is reported. The present approach is based on a Ferrier rearrangement from L-rhamnal, epoxidation of the resulting glycal and reductive opening of the isolated beta-epoxide. The 3-deoxy-alpha-rhamnoside linked to a long aglycone chain was used to ascertain by Raman vibrational spectroscopy the presence of this peculiar sugar in the inner shell of Ascaris eggs. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.04.061
• 作为产物：
  描述：

  异丙醇 、 3,4-二-O-乙酰-1,5-酐-2,6-双脱氧-L-阿拉伯-己-1-糖醇 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以77%的产率得到Acetic acid (2S,3R,6S)-6-isopropoxy-2-methyl-3,6-dihydro-2H-pyran-3-yl ester
  参考文献：
  名称：

  Synthesis and Raman spectra of 3-deoxy-α-l-rhamnosides as model sugars of the Ascaris egg shell

  摘要：

  The synthesis of two 3-deoxy-alpha-L-rhamnosides (i.e., 3,6-dideoxy-L-arabino-hexopyranosides) as models of ascaroside natural products is reported. The present approach is based on a Ferrier rearrangement from L-rhamnal, epoxidation of the resulting glycal and reductive opening of the isolated beta-epoxide. The 3-deoxy-alpha-rhamnoside linked to a long aglycone chain was used to ascertain by Raman vibrational spectroscopy the presence of this peculiar sugar in the inner shell of Ascaris eggs. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.04.061

文献信息

• Allylic rearrangement of 6-deoxyglycals having practical utility
  作者：Prakash Bhaté、Derek Horton、Waldemar Priebe

  DOI：10.1016/s0008-6215(00)90681-5

  日期：1985.12
• InBr3-catalyzed cyclization of glycosides with arylamines
  作者：Pingyuan Wang、Meining Wang、Xuefeng Zhang、Guangfu Yang、Ao Zhang

  DOI：10.1016/j.tet.2012.04.116

  日期：2012.7

  Glycals have served as excellent substrates in the glycosidation reactions with arylamines to construct both C-C and C-N linkages simultaneously. However, the high reactivity and moisture/alcohol-sensitivity is also responsible for several side reactions. Herein we reported that 2,3-unsaturated glycosides can be used as alternatives of glycals to take part in the corresponding glycosidation as well. Therefore, with 10% of InBr3 or InI3 as the catalyst, 2,3-unsaturated glycosides containing various C-1 alkoxy groups reacted with arylamines smoothly and produced the glycosidation products in moderate to good yields as a pair of diastereomers with variant diastereoselectivity. (c) 2012 Elsevier Ltd. All rights reserved.