isopropyl 4,5,6,8-tetra-O-benzyl-1,2-dideoxy-α-D-galacto-oct-3-ulo-1-enopyranoside

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: isopropyl 4,5,6,8-tetra-O-benzyl-1,2-dideoxy-α-D-galacto-oct-3-ulo-1-enopyranoside
• 英文别名: (2S,3R,4S,5S,6R)-2-ethenyl-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)-2-propan-2-yloxyoxane
• 化学式: C₃₉H₄₄O₆
• 分子量: 608.775
• InChiKey: MSPIJGMXHKBHIH-CHXCTFQWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  45
• 可旋转键数：
  16
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (Z)-3,7-anhydro-4,5,6,8-tetra-O-benzyl-2,3-dideoxy-D-galacto-oct-2-enitol 在 三氯化铝 、 4 A molecular sieve 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.67h， 生成 isopropyl 4,5,6,8-tetra-O-benzyl-1,2-dideoxy-α-D-galacto-oct-3-ulo-1-enopyranoside
  参考文献：
  名称：

  Inter- and intramolecular glycosylation of exo-glycals promoted by metallic Lewis acids

  摘要：

  exo-Glycosyl carbonates were employed for inter- and intramolecular glycosylation reactions. A number of metallic Lewis Acids and solvents were examined to enhance the reactivity. The optimum conditions were found to be the use of AlCl3 in 1-nitropropane. The method was demonstrated to be useful for the intermolecular glycosyl transfer of several nucleophiles, including simple alcohols, sugars, and amino acid derivatives; however, intramolecular glycosylations were not successful. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.04.003

文献信息

• Stereoselective glycosylation of d-galactals by diethyl phosphorochloridite- and AlCl3-assisted Ferrier rearrangement
  作者：Yen-Bo Chen、Su-I. Wang、Zi-Ping Lin、Chun-Hung Lin、Min-Tsang Hsieh、Hui-Chang Lin

  DOI：10.1016/j.tet.2014.11.027

  日期：2015.1

  α-2,3-Unsaturated galactosides were synthesized in good to excellent yields by the initial activation of d-galactals with diethyl phosphorochloridite and the subsequent glycosyl addition via Ferrier rearrangement with various O-nucleophiles in the presence of AlCl3. The two-step reactions were carried out in one-pot and finished within 60 min in 81–95% yield to give the glycoside products with excellent

  通过以二乙基次氯代磷酸酯初次激活d-半乳糖，然后在AlCl 3存在下，通过与各种O-亲核试剂的Ferrier重排加成糖基，以良好至极佳的产率合成了α-2,3-不饱和半乳糖苷。两步反应在一个反应​​釜中进行，并在60分钟内完成，收率为81-95％，使糖苷产物具有出色的α-立体选择性。
• Stereoselective glycosylation of exo-glycals by microwave-assisted Ferrier rearrangement
  作者：Hui-Chang Lin、Chih-Chun Chang、Jia-Yi Chen、Chun-Hung Lin

  DOI：10.1016/j.tetasy.2004.11.044

  日期：2005.1

  exo-Glycosyl carbonates were shown to be efficient glycosyl donors in microwave-assisted glycosylation. In these reactions alpha-glycosyl additions occurred with excellent stereoselectivity and were complete in 4-8 min with 75-92% yield. Interestingly exo-glycals were found to have higher activity than endo-glycals and common glycosides, the reactions of which can be improved by the addition of Lewis acid to result in a higher yield and enhanced stereo selectivity. (C) 2004 Elsevier Ltd. All rights reserved.
• Inter- and intramolecular glycosylation of exo-glycals promoted by metallic Lewis acids
  作者：Sheng-Jie Hsu、Hui-Chang Lin、Chun-Hung Lin

  DOI：10.1016/j.carres.2006.04.003

  日期：2006.7

  exo-Glycosyl carbonates were employed for inter- and intramolecular glycosylation reactions. A number of metallic Lewis Acids and solvents were examined to enhance the reactivity. The optimum conditions were found to be the use of AlCl3 in 1-nitropropane. The method was demonstrated to be useful for the intermolecular glycosyl transfer of several nucleophiles, including simple alcohols, sugars, and amino acid derivatives; however, intramolecular glycosylations were not successful. (c) 2006 Elsevier Ltd. All rights reserved.