(Z)-3,7-anhydro-4,5,6,8-tetra-O-benzyl-1-O-tert-butoxycarbonyl-2,3-dideoxy-D-galacto-oct-2-enitol | 848844-32-6

• 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: (Z)-3,7-anhydro-4,5,6,8-tetra-O-benzyl-1-O-tert-butoxycarbonyl-2,3-dideoxy-D-galacto-oct-2-enitol
• 英文别名: tert-butyl [(2Z)-2-[(3R,4S,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-ylidene]ethyl] carbonate
• CAS: 848844-32-6
• 化学式: C₄₁H₄₆O₈
• 分子量: 666.811
• InChiKey: ICXCOWZJDZOQSU-PEANOSKMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  49
• 可旋转键数：
  18
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  81.7
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Boc-L-丝氨酸甲酯 、 (Z)-3,7-anhydro-4,5,6,8-tetra-O-benzyl-1-O-tert-butoxycarbonyl-2,3-dideoxy-D-galacto-oct-2-enitol 在 三氯化铝 、 4 A molecular sieve 作用下， 以 various solvent(s) 为溶剂， 反应 0.67h， 以75%的产率得到O-(4,5,6,8-tetra-O-benzyl-1,2-dideoxy-α-D-galacto-oct-3-ulo-1-enopyranosyl)-N-tert-butoxycarbonyl-L-serine methyl ester
  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
• 作为产物：
  描述：

  N-Boc-咪唑 、 (Z)-3,7-anhydro-4,5,6,8-tetra-O-benzyl-2,3-dideoxy-D-galacto-oct-2-enitol 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以90%的产率得到(Z)-3,7-anhydro-4,5,6,8-tetra-O-benzyl-1-O-tert-butoxycarbonyl-2,3-dideoxy-D-galacto-oct-2-enitol
  参考文献：
  名称：

  Stereoselective glycosylation of exo-glycals by microwave-assisted Ferrier rearrangement

  摘要：

  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.

  DOI：

  10.1016/j.tetasy.2004.11.044

文献信息

• 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.