(2S,3R)-2,4-bis(benzyloxy)-3-(tert-butyldimethylsilanyloxy)butyraldehyde | 163041-09-6

• 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: (2S,3R)-2,4-bis(benzyloxy)-3-(tert-butyldimethylsilanyloxy)butyraldehyde
• 英文别名: (2S,3R)-3-[tert-butyl(dimethyl)silyl]oxy-2,4-bis(phenylmethoxy)butanal
• CAS: 163041-09-6
• 化学式: C₂₄H₃₄O₄Si
• 分子量: 414.617
• InChiKey: FEBXUGYVAKEUMY-DHIUTWEWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.38
• 重原子数：
  29
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,3R)-2,4-bis(benzyloxy)-3-(tert-butyldimethylsilanyloxy)butyraldehyde 在 三乙基硼 、 三氟甲磺酸 、 四丁基氟化铵 、 二异丁基氢化铝 、 溶剂黄146 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 2,4,6-tri-O-benzyl-α,β-D-galactopyranose
  参考文献：
  名称：

  The Asymmetric Synthesis ofd-Galactose via an Iterativesyn-Glycolate Aldol Strategy

  摘要：

  通过迭代的合成-乙醇醛酸策略，从简单的起始原料出发，经过八个步骤完成了 d-半乳糖的不对称合成，收率大于 14%。

  DOI：

  10.1055/s-2002-34215
• 作为产物：
  描述：

  1,3-O-Dibenzyl-2-O-(tert-butyldimethylsilyl)threitol 生成 (2S,3R)-2,4-bis(benzyloxy)-3-(tert-butyldimethylsilanyloxy)butyraldehyde
  参考文献：
  名称：

  Preferred conformation of C-glycosides. 10. Synthesis and conformational analysis of carbon trisaccharides

  摘要：

  A flexible and efficient synthesis of the carbon trisaccharide 2 related to the Type II O(H) blood group determinant has been developed. This route was applied to the synthesis of the trisaccharides 3, 4, and 5. The preferred solution conformations of compounds 2-5 were determined on the basis of vicinal coupling constants in the H-1 NMR spectrum. Each of the four trisaccharides adopts a distinct and well-defined solution conformation in accord with the predictions made on the basis of the preference of the C-glycosidic bond for the ''exo-anomeric'' conformation and the analysis of 1,3-diaxial-like interactions around the C-aglyconic bond.

  DOI：

  10.1021/jo00028a019

文献信息

• The Asymmetric Synthesis of<scp>d</scp>-Galactose via an Iterative<i>syn</i>-Glycolate Aldol Strategy
  作者：Stephen G. Davies、Rebecca L. Nicholson、Andrew D. Smith

  DOI：10.1055/s-2002-34215

  日期：——

  The asymmetric synthesis of d-galactose has been completed in eight steps and in >14% yield from simple starting materials via an iterative syn-glycolate aldol strategy.

  通过迭代的合成-乙醇醛酸策略，从简单的起始原料出发，经过八个步骤完成了 d-半乳糖的不对称合成，收率大于 14%。
• Preferred conformation of C-glycosides. 10. Synthesis and conformational analysis of carbon trisaccharides
  作者：Toru Haneda、Peter G. Goekjian、Sung H. Kim、Yoshito Kishi

  DOI：10.1021/jo00028a019

  日期：1992.1

  A flexible and efficient synthesis of the carbon trisaccharide 2 related to the Type II O(H) blood group determinant has been developed. This route was applied to the synthesis of the trisaccharides 3, 4, and 5. The preferred solution conformations of compounds 2-5 were determined on the basis of vicinal coupling constants in the H-1 NMR spectrum. Each of the four trisaccharides adopts a distinct and well-defined solution conformation in accord with the predictions made on the basis of the preference of the C-glycosidic bond for the ''exo-anomeric'' conformation and the analysis of 1,3-diaxial-like interactions around the C-aglyconic bond.
• Preferred Conformations of C-Glycosides. 14. Synthesis and Conformational Analysis of Carbon Analogs of the Blood Group Determinant H-Type II
  作者：Alexander Wei、Arnaud Haudrechy、Catharine Audin、Hyuk-Sang Jun、Nathalie Haudrechy-Bretel、Yoshito Kishi

  DOI：10.1021/jo00112a040

  日期：1995.4

  The syntheses of C-trisaccharides 1-4, carbon analogs of the human blood group determinant II-type II, have been achieved in a flexible and efficient manner. Vicinal coupling constants in the H-1 NMR spectrum provide experimental evidence that each of the four compounds 1-4 possesses a unique solution conformation, in accord with the predictions made on the basis of the preference of the C-glycosidic bond for the ''exo-anomeric'' conformation and the influence of 1,3-diaxial like interactions about the C-aglyconic bond.
• A SuperQuat glycolate aldol approach to the asymmetric synthesis of hexose monosaccharides
  作者：Stephen G. Davies、Rebecca L. Nicholson、Andrew D. Smith

  DOI：10.1039/b415943h

  日期：——

  A stereoselective two-carbon homologation protocol has been developed and applied to the asymmetric synthesis of the hexose monosaccharides D-galactose, D-fucose, D-idose, D-6-deoxyidose, D-talose and D-6-deoxytalose.

  我们开发了一种立体选择性双碳同源化方案，并将其应用于 D-半乳糖、D-岩藻糖、D-idose、D-6-脱氧idose、D-塔罗糖和 D-6-deoxytalose 六糖单糖的不对称合成。