3-O-chloroacetyl-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose | 99813-91-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-O-chloroacetyl-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose
• 英文别名: [(3aR,5R,6S,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl] 2-chloroacetate
• CAS: 99813-91-9
• 化学式: C₁₄H₂₁ClO₇
• 分子量: 336.77
• InChiKey: ICACZLQLRMYWIR-DVYMNCLGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-O-chloroacetyl-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 在 sodium azide 、 tetrakis(actonitrile)copper(I) hexafluorophosphate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 32.0h， 生成 [(3aR,5R,6S,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl] 2-[4-(3,5-ditert-butylphenyl)triazol-1-yl]acetate
  参考文献：
  名称：

  机械平面手性轮烷的有效方法

  摘要：

  我们描述了第一种在不使用手性分离技术的情况下生产具有优异对映纯度的机械平面手性轮烷的方法，并且首次明确指定了产品的绝对立体化学。这项概念验证研究采用手性池糖作为不对称源，并采用高产活性模板反应来形成机械键，最终为详细研究这些具有挑战性的目标打开了大门。

  DOI：

  10.1021/ja412715m
• 作为产物：
  描述：

  3-O-[(t-butyl)dimethylsilyl]-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 在 吡啶 、 potassium fluoride 、 四丁基溴化铵 作用下， 以 水 、 乙腈 为溶剂， 反应 0.16h， 生成 3-O-chloroacetyl-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose
  参考文献：
  名称：

  RAPID CARBOHYDRATE PROTECTING GROUP MANIPULATIONS ASSISTED BY MICROWAVE DIELECTRIC HEATING

  摘要：

  The protocols for oligosaccharide synthesis are often tedious due to extended synthetic routes and reaction times. We herein describe methods assisted by microwave dielectric heating, which enable very short reaction times and high yields for the introduction and removal of eleven of the most commonly used protecting groups in carbohydrate syntheses. Several examples are reported, where solid supported reagents in combination with microwave dielectric heating have been used. This results in both faster and easier synthesis and purification.

  DOI：

  10.1081/car-100105712

文献信息

• Acylation of carbohydrates over Al2O3: preparation of partially and fully acylated carbohydrate derivatives and acetylated glycosyl chlorides
  作者：Pallavi Tiwari、Anup Kumar Misra

  DOI：10.1016/j.carres.2005.11.035

  日期：2006.2

  protocol does not require the addition of any base or activator. This methodology has been further extended to the selective acylation of carbohydrate diols and the one-pot preparation of acetylated glycosyl chlorides direct from free reducing sugars. The yields obtained in most of the cases are excellent.

  据报道，使用酰氯和固体支持剂Al2O3对碳水化合物衍生物进行选择性和全O酰化。该协议不需要添加任何碱或活化剂。该方法已经进一步扩展到碳水化合物二醇的选择性酰化和直接从游离还原糖直接制备一锅乙酰化糖基氯的方法。在大多数情况下所获得的产量是极好的。
• An improved procedure for the synthesis of sugar chloroacetates and some substitution reactions thereof
  作者：Gordon J. F. Chittenden、Henk Regeling

  DOI：10.1002/recl.19871060202

  日期：——

  An improved and simplified procedure for the preparation of some sugar chloroacetates is described. Nucleophilic substitution of the chlorine atom in some of the products yields the corresponding α-substituted acetate esters.

  描述了一种用于制备一些糖氯乙酸盐的改进和简化的方法。在一些产物中氯原子的亲核取代产生相应的α-取代的乙酸酯。
• RAPID CARBOHYDRATE PROTECTING GROUP MANIPULATIONS ASSISTED BY MICROWAVE DIELECTRIC HEATING
  作者：Eva Söderberg、Jacob Westman、Stefan Oscarson*

  DOI：10.1081/car-100105712

  日期：2001.6.30

  The protocols for oligosaccharide synthesis are often tedious due to extended synthetic routes and reaction times. We herein describe methods assisted by microwave dielectric heating, which enable very short reaction times and high yields for the introduction and removal of eleven of the most commonly used protecting groups in carbohydrate syntheses. Several examples are reported, where solid supported reagents in combination with microwave dielectric heating have been used. This results in both faster and easier synthesis and purification.
• An Efficient Approach to Mechanically Planar Chiral Rotaxanes
  作者：Robert J. Bordoli、Stephen M. Goldup

  DOI：10.1021/ja412715m

  日期：2014.4.2

  method for production of mechanically planar chiral rotaxanes in excellent enantiopurity without the use of chiral separation techniques and, for the first time, unambiguously assign the absolute stereochemistry of the products. This proof-of-concept study, which employs a chiral pool sugar as the source of asymmetry and a high-yielding active template reaction for mechanical bond formation, finally opens

  我们描述了第一种在不使用手性分离技术的情况下生产具有优异对映纯度的机械平面手性轮烷的方法，并且首次明确指定了产品的绝对立体化学。这项概念验证研究采用手性池糖作为不对称源，并采用高产活性模板反应来形成机械键，最终为详细研究这些具有挑战性的目标打开了大门。