4,5,6,8-tetra-O-benzyl-1,2-dideoxy-α-D-galacto-oct-3-ulo-1-enopyranosyl-(3->6)-1,2:3,4-diisopropylidine-α-D-galactopyranose | 517914-92-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4,5,6,8-tetra-O-benzyl-1,2-dideoxy-α-D-galacto-oct-3-ulo-1-enopyranosyl-(3->6)-1,2:3,4-diisopropylidine-α-D-galactopyranose
• 英文别名: (1S,2R,6R,8R,9S)-8-[[(2S,3R,4S,5S,6R)-2-ethenyl-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxymethyl]-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecane
• CAS: 517914-92-0
• 化学式: C₄₈H₅₆O₁₁
• 分子量: 808.966
• InChiKey: FJNWHBWHWCYIES-YUNLDCCZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  59
• 可旋转键数：
  17
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  102
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  4,5,6,8-tetra-O-benzyl-1,2-dideoxy-α-D-galacto-oct-3-ulo-1-enopyranosyl-(3->6)-1,2:3,4-diisopropylidine-α-D-galactopyranose 在 臭氧 、 二甲基硫 作用下， 以80%的产率得到(2R,3R,4S,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)-2-[[(1S,2R,6R,8R,9S)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-8-yl]methoxy]oxane-2-carbaldehyde
  参考文献：
  名称：

  Stereoselective Glycosylation of exo-Glycals Accelerated by Ferrier-Type Rearrangement

  摘要：

  [GRAPHIC]Owing to the driving force of the Ferrier-type rearrangement, the exo-glycals are highly reactive with various alcohols to afford glycosides and glycoconjugates with exclusive alpha-configuration. The resulting vinyl group in these glycosylation products can be further elaborated for general applications, including the synthesis of spiro derivatives and glycosylation of 2-ketoaldonic acids.

  DOI：

  10.1021/ol034130z
• 作为产物：
  描述：

  双丙酮半乳糖 、 Acetic acid 2-[(3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-(2Z)-ylidene]-ethyl ester 在 4 Angstroem MS 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 以90%的产率得到4,5,6,8-tetra-O-benzyl-1,2-dideoxy-α-D-galacto-oct-3-ulo-1-enopyranosyl-(3->6)-1,2:3,4-diisopropylidine-α-D-galactopyranose
  参考文献：
  名称：

  Stereoselective Glycosylation of exo-Glycals Accelerated by Ferrier-Type Rearrangement

  摘要：

  [GRAPHIC]Owing to the driving force of the Ferrier-type rearrangement, the exo-glycals are highly reactive with various alcohols to afford glycosides and glycoconjugates with exclusive alpha-configuration. The resulting vinyl group in these glycosylation products can be further elaborated for general applications, including the synthesis of spiro derivatives and glycosylation of 2-ketoaldonic acids.

  DOI：

  10.1021/ol034130z

文献信息

• 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.
• 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.
• Stereoselective Glycosylation of <i>exo</i>-Glycals Accelerated by Ferrier-Type Rearrangement
  作者：Hui-Chang Lin、Wen-Bin Yang、Yu-Feng Gu、Chen、Chung-Yi Wu、Chun-Hung Lin

  DOI：10.1021/ol034130z

  日期：2003.4.1

  [GRAPHIC]Owing to the driving force of the Ferrier-type rearrangement, the exo-glycals are highly reactive with various alcohols to afford glycosides and glycoconjugates with exclusive alpha-configuration. The resulting vinyl group in these glycosylation products can be further elaborated for general applications, including the synthesis of spiro derivatives and glycosylation of 2-ketoaldonic acids.