2-(2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl)acetaldehyde | 120520-80-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl)acetaldehyde
• 英文别名: 2-(2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl)ethanal；(2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl)-ethanal；2-[(2S,3R,4R,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]acetaldehyde
• CAS: 120520-80-1
• 化学式: C₃₆H₃₈O₆
• 分子量: 566.694
• InChiKey: WTNFDXKLFWOMIR-BHSUMJALSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  42
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl)acetaldehyde 在 sodium hydroxide 、 sodium cyanoborohydride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成
  参考文献：
  名称：

  设计和合成唾液酸化的Lewis x模拟物作为E-选择素抑制剂。

  摘要：

  描述了抑制唾液酸路易斯x与E-选择素结合的新型β-C-甘露糖苷的设计和合成。发现在C-6位上含有苯基取代基的化合物具有增强的效力。

  DOI：

  10.1016/s0960-894x(00)00623-5
• 作为产物：
  描述：

  2,3,4,6-tetra-O-benzyl-D-mannopyranose 在 sodium hydride 、 二异丁基氢化铝 作用下， 以 二氯甲烷 为溶剂， 生成 2-(2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl)acetaldehyde
  参考文献：
  名称：

  设计和合成唾液酸化的Lewis x模拟物作为E-选择素抑制剂。

  摘要：

  描述了抑制唾液酸路易斯x与E-选择素结合的新型β-C-甘露糖苷的设计和合成。发现在C-6位上含有苯基取代基的化合物具有增强的效力。

  DOI：

  10.1016/s0960-894x(00)00623-5

文献信息

• Oxygenated allylic silanes: useful homoenolate equivalents for the stereoselective C-glycosidation of pyranoside derivatives
  作者：James S. Panek、Michelle A. Sparks

  DOI：10.1021/jo00270a005

  日期：1989.4
• Domino Heck/Lactonization-Catalyzed Synthesis of 3-<i>C</i>-Linked Mannopyranosyl Coumarins
  作者：Denis Giguère、Philipe Cloutier、René Roy

  DOI：10.1021/jo901855p

  日期：2009.11.6

  Selective syntheses of methyl alpha- (8) and beta-C-mannopyranosyl acrylates (9) were obtained from alpha-C-allyl mannopyranoside (3) by ozonolysis to 4 followed by alpha-methylenation to provide intermediate aldehydes 5 and 6. The beta-anomer 6 was obtained by in situ anomeric epimerization. The acrylates and the homologous alpha-anomer 16, obtained by oxidative hydroboration, oxidation, and alpha-methylenation, were converted into 3-C-linked mannopyranosyl coumarins 11, 12,and 19 in good yields under one-pot Heck/lactonization conditions.
• Microwave-Assisted Organocatalytic Anomerization of α-<i>C</i>-Glycosylmethyl Aldehydes and Ketones
  作者：Alessandro Massi、Andrea Nuzzi、Alessandro Dondoni

  DOI：10.1021/jo701959b

  日期：2007.12.1

  [GRAPHICS]The use of L-proline (30 mol %) and MW irradiation (13 W) with cooling promotes in a few hours the almost quantitative anomerization of alpha-C-glycosylmethyl aldehydes into beta-isomers. An open-chain enamine-based mechanism is postulated for this transformation. The anomerization of alpha-ketones was instead achieved by the pyrrolidine/TFA couple and MW irradiation at 120 degrees C (enamine mechanism) and by DBU as Bronsted base (enolate mechanism).
• Use of 1JC1, H1 values for the stereochemical determination of C-glycosides: A simple two dimensional NMR protocol
  作者：Michelle A. Sparks、James S. Panek

  DOI：10.1016/s0040-4039(00)95213-4

  日期：1989.1
• General Synthesis of <i>C</i>-Glycosyl Amino Acids via Proline-Catalyzed Direct Electrophilic α-Amination of <i>C</i>-Glycosylalkyl Aldehydes
  作者：Andrea Nuzzi、Alessandro Massi、Alessandro Dondoni

  DOI：10.1021/ol801685x

  日期：2008.10.16

  Non-natural axially and equatorially linked C-glycosyl alpha-amino acids (glycines, alanines, and CH2-serine isosteres) with either S or R alpha-configuration were prepared by D- and L-proline-catalyzed (de > 95%) alpha-amination of C-glycosylalkyl aldehydes using dibenzyl azodicarboxylate as the electrophilic reagent.