cyclohexyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-threo-hex-2-enopyranoside | 69308-04-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: cyclohexyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-threo-hex-2-enopyranoside
• 英文别名: [(2R,3R,6S)-3-acetyloxy-6-cyclohexyloxy-3,6-dihydro-2H-pyran-2-yl]methyl acetate
• CAS: 69308-04-9
• 化学式: C₁₆H₂₄O₆
• 分子量: 312.363
• InChiKey: PRTOYGXCUGXISF-OAGGEKHMSA-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 、 D-三乙酰半乳糖烯 在 carbon immobilized iron (III) chloride hexahydrate 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 以82%的产率得到cyclohexyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-threo-hex-2-enopyranoside
  参考文献：
  名称：

  FeCl₃·6H₂O/C: An Efficient and Recyclable Catalyst for the Synthesis of 2,3-UnsaturatedO-andS-Glycosides

  摘要：

  DOI：

  10.1080/07328303.2014.941995

文献信息

• Reactivity switching and selective activation of C-1 or C-3 in 2,3-unsaturated thioglycosides
  作者：Arunima Mukherjee、Narayanaswamy Jayaraman

  DOI：10.1016/j.carres.2011.04.039

  日期：2011.9

  activation of C-1 or C-3 in 2,3-unsaturated thioglycosides, namely, 2,3-dideoxy-1-thio-D-hex-2-enopyranosides are reported. The reactivity switching allowed activation of either C-1 or C-3, with the use of either N-iodosuccinimide (NIS)/triflic acid (TfOH) or TfOH alone. C-1 glycosylation with alcohol acceptors occurred in the presence of NIS/TfOH, without the acceptors reacting at C-3. On the other

  据报道在2，3-不饱和硫代糖苷，即2，3-二脱氧-1-硫代-D-hex-2-enopyranosides中的C-1或C-3的反应性转换和选择性活化。反应性转换允许单独使用N-碘琥珀酰亚胺（NIS）/三氟甲磺酸（TfOH）或TfOH活化C-1或C-3。在NIS / TfOH存在下，用醇受体进行的C-1糖基化反应不会使受体在C-3处发生反应。另一方面，2，3-不饱和硫代糖苷与三氟甲磺酸介导的醇的反应导致C-1乙硫基分子内转位至C-3，形成3-乙硫基糖。所得的糖用醇进行糖基化，得到3-乙硫基-2-脱氧糖苷。但是，当使用硫醇作为受体时，仅在C-3处产生立体选择性加成，从而形成C-1，
• Yadav, Ram Naresh; Banik, Indrani; Banik, Bimal Krishna, Journal of the Indian Chemical Society, 2018, vol. 95, # 11, p. 1385 - 1387
  作者：Yadav, Ram Naresh、Banik, Indrani、Banik, Bimal Krishna

  DOI：——

  日期：——
• Microwave-induced, Montmorillonite K10-catalyzed Ferrier rearrangement of tri-O-acetyl-d-galactal: mild, eco-friendly, rapid glycosidation with allylic rearrangement
  作者：Bhagavathy Shanmugasundaram、Ajay K. Bose、Kalpattu K. Balasubramanian

  DOI：10.1016/s0040-4039(02)01517-4

  日期：2002.9

  Montmorillonite K10 was found to catalyze, under microwave irradiation, rapid O-glycosidation of 3,4,6-tri-O-acetyl-D-galactal to afford exclusively the alkyl and aryl 2,3-dideoxy-D-threo-hex-2-enopyranosides with very high alpha-selectivity and without the formation of the 2-deoxy-D-lyxo-hexopyranosides. Under these conditions, 3,4,6-tri-O-acetyl-D-glucal as usual also underwent the Ferrier rearrangement. (C) 2002 Elsevier Science Ltd. All rights reserved.