6-O-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)-1,2:3,4-diisopropylidene-α-D-galactopyranose

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 6-O-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)-1,2:3,4-diisopropylidene-α-D-galactopyranose
• 英文别名: 2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl-(1→6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose；[(2R,3S,4S,5R,6R)-3,4,5-tris(2,2-dimethylpropanoyloxy)-6-[[(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]oxan-2-yl]methyl 2,2-dimethylpropanoate
• 化学式: C₃₈H₆₂O₁₅
• 分子量: 758.901
• InChiKey: RWCCQAVSWQVFOA-CJBKXDKDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  53
• 可旋转键数：
  16
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  170
• 氢给体数：
  0
• 氢受体数：
  15

反应信息

• 作为产物：
  描述：

  N-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)-p-anisamide 在 四溴化碳 、 三乙胺 、 三苯基膦 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 8.0h， 生成 6-O-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)-1,2:3,4-diisopropylidene-α-D-galactopyranose
  参考文献：
  名称：

  N-糖基酰胺作为立体选择性糖基化反应中的糖基供体

  摘要：

  由于它们的高稳定性，N-糖基酰胺迄今为止还没有被认为是糖基化反应的糖基供体。本文描述了在温和反应条件下裂解异头酰胺官能团的两种新程序，以及活化糖基供体与醇和胺的进一步立体选择性原位转化以产生 β-构型的 O-和 N-糖苷。

  DOI：

  10.1055/s-2004-834911

文献信息

• Metal-free and VOC-free O-glycosylation in supercritical CO₂
  作者：Adrià Cardona、Omar Boutureira、Sergio Castillón、Yolanda Díaz、M. Isabel Matheu

  DOI：10.1039/c7gc00722a

  日期：——

  Supercritical carbon dioxide (scCO2) is a suitable medium to perform transition metal-free glycosylations in the absence of volatile organic solvents (VOCs) using glycosyl halides as glycosyl donors. The methodology here described can be applied for obtaining O-glycosides in a totally green reaction, as well as orthoesters, depending on the reaction conditions. The process is much more sensitive to

  超临界二氧化碳（sc CO 2）是一种合适的介质，可在无挥发性有机溶剂（VOC）的情况下使用糖基卤化物作为糖基供体来进行无过渡金属的糖基化反应。根据反应条件，此处描述的方法可用于在完全绿色反应以及原酸酯中获得O-糖苷。该方法对温度的变化比对压力的改变更为敏感，与糖基溴相比，糖基氯化物需要更高的温度才能被活化。新戊酰基作为良好的CO 2-亲和单元，并被证明是获得良好立体选择性的最佳选择。流体性质和超临界条件的相关性也得到了证明
• N-Glycosyl Amides: Removal of the Anomeric Protecting Group and Conversion into Glycosyl Donors
  作者：Norbert Pleuss、Horst Kunz

  DOI：10.1002/anie.200351351

  日期：2003.7.14
• The Chemistry of Isopropenyl Glycopyranosides. Transglycosylations and Other Reactions
  作者：H. Keith Chenault、Alfredo Castro、Laura F. Chafin、Jie Yang

  DOI：10.1021/jo960190p

  日期：1996.1.1

  Various anomerically pure isopropenyl alpha- and beta-glycopyranosides have been synthesized and shown to undergo synthetically useful transglycosylation reactions with a variety of primary and secondary carbohydrate alcohols. Although stable when stored, isopropenyl glycosides are readily activated as glycosyl donors by a variety of electrophiles, including N-iodosuccinimide/triflic acid, trimethylsilyl triflate, and triflic anhydride. Under conditions that retard formation of the glycosyl cation, the reactivity of isopropenyl glycosides is diverted away from transglycosylation and toward electrophilic addition across the vinyl ether double bond.
• <i>N</i>-Glycosyl Amides as Glycosyl Donors in Stereoselective Glycosylation Reactions
  作者：Horst Kunz、Norbert Pleuss

  DOI：10.1055/s-2004-834911

  日期：——

  Due to their high stability, N-glycosyl amides have so far not been considered as glycosyl donors for glycosylation reactions. Two new procedures for the cleavage of the anomeric amide functionality under mild reaction conditions and further stereoselective in situ conversions of the activated glycosyl donors with alcohols and amines to give β-configured O- and N-glycosides are described in this article

  由于它们的高稳定性，N-糖基酰胺迄今为止还没有被认为是糖基化反应的糖基供体。本文描述了在温和反应条件下裂解异头酰胺官能团的两种新程序，以及活化糖基供体与醇和胺的进一步立体选择性原位转化以产生 β-构型的 O-和 N-糖苷。