isopropenyl 2,3,4,6-tetra-O-benzyl-α,β-D-glucopyranosyl carbonate | 139608-01-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: isopropenyl 2,3,4,6-tetra-O-benzyl-α,β-D-glucopyranosyl carbonate
• 英文别名: prop-1-en-2-yl [(3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl] carbonate
• CAS: 139608-01-8；139608-02-9；139608-05-2；139608-06-3
• 化学式: C₃₈H₄₀O₈
• 分子量: 624.731
• InChiKey: FJQFPPDGAXLCOF-YGMGGQQPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  46
• 可旋转键数：
  17
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  氘代乙腈 、 isopropenyl 2,3,4,6-tetra-O-benzyl-α,β-D-glucopyranosyl carbonate 在 三氟甲磺酸三甲基硅酯 作用下， 反应 24.0h， 以40%的产率得到
  参考文献：
  名称：

  糖基化反应中腈中间体的构象分析

  摘要：

  为了阐明乙腈介导的糖基化反应的立体选择性，已在-30°C的乙腈-d3中生成了腈中间体，并通过1H，13C和15N NMR光谱进行了研究。结合起来，利用CHARMm力场对中间体进行了分子建模。所有证据表明，仅形成具有α构型的腈衍生物。

  DOI：

  10.1016/0008-6215(93)84021-w

文献信息

• Isopropenyl glycosides and congeners as novel classes of glycosyl donors: theme and variations
  作者：Alberto Marra、Jacques Esnault、Alain Veyrieres、Pierre Sinay

  DOI：10.1021/ja00042a010

  日期：1992.7

  Isopropenyl glycosides (i.e., 10 and 11) have been synthesized in high yields by reacting the corresponding anomeric acetates with the Tebbe reagent. These compounds undergo glycosylation with primary or secondary carbohydrate alcohols in the presence of trimethylsilyl triflate or boron trifluoride etherate, probably via a mixed acetal glycoside intermediate. On the basis of this principle, a quite efficient glycosylation of monosaccharide hemiacetal donors (i.e., 1, 7, and 9) with acceptors bearing an isopropenyl ether function at a primary or secondary position (i.e., 18 and 21) has been developed. Also investigated were the glycosylating properties of isopropenyl glucosyl and galactosyl carbonates (i.e., 12-15), easily prepared from the corresponding hemiacetals, toward sugar alcohols. In each case, the beta-selective synthesis of disaccharides from donors having nonparticipating groups at C-2 was ensured by the use of acetonitrile, at low temperature, as the solvent.
• Conformational analysis of nitrilium intermediates in glycosylation reactions
  作者：I. Braccini、C. Derouet、J. Esnault、C.Herv′e de Penhoat、J.-M. Mallet、V. Michon、P. Sinaÿ

  DOI：10.1016/0008-6215(93)84021-w

  日期：1993.8

  In order to shed light on the stereoselectivity of acetonitrile-mediated glycoslation reactions, the nitrilium intermediates have been genegrated at —30°C in acetonintrile-d3 and studied by 1H, 13C, and 15N NMR spectroscopy. Conjointly, molecular modeling of the intermediates by molecular mechanics has been performed with the CHARMm force field. All the evidence suggests that only nitrilium derivatives

  为了阐明乙腈介导的糖基化反应的立体选择性，已在-30°C的乙腈-d3中生成了腈中间体，并通过1H，13C和15N NMR光谱进行了研究。结合起来，利用CHARMm力场对中间体进行了分子建模。所有证据表明，仅形成具有α构型的腈衍生物。