phenyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-threo-hex-2-enopyranoside | 69247-21-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: phenyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-threo-hex-2-enopyranoside
• 英文别名: 2'-iodobenzyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-eno-pyranoside；[(2R,3R,6R)-3-acetyloxy-6-phenoxy-3,6-dihydro-2H-pyran-2-yl]methyl acetate
• CAS: 69247-21-8
• 化学式: C₁₆H₁₈O₆
• 分子量: 306.315
• InChiKey: YLYGQKOUMQKYKQ-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：
  0.38
• 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：

  D-三乙酰半乳糖烯 、 苯酚 在 Montmorillonite K₁₀ 作用下， 以 氯苯 为溶剂， 反应 0.13h， 生成 phenyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-threo-hex-2-enopyranoside 、 phenyl 4,6-di-O-acetyl-2,3-dideoxy-β-D-threo-hex-2-enopyranoside
  参考文献：
  名称：

  Microwave-induced, Montmorillonite K10-catalyzed Ferrier rearrangement of tri-O-acetyl-d-galactal: mild, eco-friendly, rapid glycosidation with allylic rearrangement

  摘要：

  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.

  DOI：

  10.1016/s0040-4039(02)01517-4

文献信息

• Niobium(V) chloride catalyzed microwave assisted synthesis of 2,3-unsaturated O-glycosides by the Ferrier reaction
  作者：Srinivas Hotha、Ashish Tripathi

  DOI：10.1016/j.tetlet.2005.05.015

  日期：2005.7

  NbCl5 catalyzes the Ferrier reaction of per-O-acetylated glycals with primary, secondary, allylic, benzylic and monosaccharide alcohols to give 2,3-unsaturated α-glycosides in short reaction times under microwave irradiation conditions.

  NbCl 5催化过-O-乙酰化的糖与伯，仲，烯丙基，苄基和单糖醇的Ferrier反应，在微波辐射条件下，在较短的反应时间内即可生成2,3-不饱和的α-糖苷。
• Sobhana Babu; Balasubramanian, Synthetic Communications, 1999, vol. 29, # 24, p. 4299 - 4305
  作者：Sobhana Babu、Balasubramanian

  DOI：——

  日期：——