3,4-Di-O-acetyl-6-O-benzyl-D-glucal | 71110-96-8

• 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: 3,4-Di-O-acetyl-6-O-benzyl-D-glucal
• 英文别名: [(2R,3S,4R)-3-acetyloxy-2-(phenylmethoxymethyl)-3,4-dihydro-2H-pyran-4-yl] acetate
• CAS: 71110-96-8
• 化学式: C₁₇H₂₀O₆
• 分子量: 320.342
• InChiKey: HDAIVKGQDUTFTN-ZACQAIPSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,4-Di-O-acetyl-6-O-benzyl-D-glucal 在 水 、 lithium bromide 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以85%的产率得到3,4-di-O-acetyl-6-O-benzyl-2-deoxy-D-glucopyranose
  参考文献：
  名称：

  Organoboron-Catalyzed Regio- and Stereoselective Formation of β-2-Deoxyglycosidic Linkages

  摘要：

  A borinic acid derived catalyst enables regioselective and β-selective reactions of 2-deoxy- and 2,6-dideoxyglycosyl chloride donors with pyranoside-derived acceptors having unprotected cis-1,2- and 1,3-diol groups. The use of catalysis to promote a β-selective pathway by enhancement of acceptor nucleophilicity constitutes a distinct approach from previous work, which has been aimed at modulating donor reactivity by variation of protective and/or leaving groups.

  DOI：

  10.1021/ol501711v
• 作为产物：
  描述：

  D-葡萄烯糖 在 吡啶 、 二苯基酸 、 silver(l) oxide 作用下， 以 乙腈 为溶剂， 反应 34.0h， 生成 3,4-Di-O-acetyl-6-O-benzyl-D-glucal
  参考文献：
  名称：

  Organoboron-Catalyzed Regio- and Stereoselective Formation of β-2-Deoxyglycosidic Linkages

  摘要：

  A borinic acid derived catalyst enables regioselective and β-selective reactions of 2-deoxy- and 2,6-dideoxyglycosyl chloride donors with pyranoside-derived acceptors having unprotected cis-1,2- and 1,3-diol groups. The use of catalysis to promote a β-selective pathway by enhancement of acceptor nucleophilicity constitutes a distinct approach from previous work, which has been aimed at modulating donor reactivity by variation of protective and/or leaving groups.

  DOI：

  10.1021/ol501711v

文献信息

• Sodium Borohydride-Nickel Chloride-Methanol Catalytic System for Regioselective Reduction of Electron-Rich Conjugated Dienes and Reductive Cleavage of Allyl Esters Involving π-Allylnickel Intermediates
  作者：Biao-Lin Yin、Cong-Bi Cai、Jin-Qiang Lai、Ze-Ren Zhang、Li Huang、Li-Wen Xu、Huan-Feng Jiang

  DOI：10.1002/adsc.201100612

  日期：2011.12

  The regioslective reduction of electron-rich dienes to monoolefins and the reductive cleavage of allyl esters were fulfilled by employing a sodium borohydride-nickel chloride-methanol catalytic system with exceedingly simple manipulations and high functional group tolerability. Both of the reductive reactions may involve π-allylnickel intermediates generated from fresh nickel boride.

  富电子二烯向单烯烃的区域反射还原和烯丙基酯的还原裂解是通过使用硼氢化钠-氯化镍-甲醇催化系统完成的，该系统操作极其简单，并且对官能团的耐受性极高。两种还原反应都可能涉及由新鲜的硼化镍产生的π-烯丙基镍中间体。
• Electrochemical formation of glycals in THF
  作者：J.D Parrish、R.Daniel Little

  DOI：10.1016/s0040-4039(01)01544-1

  日期：2001.10

  existing electrochemical approaches to these types of species and is amenable to scale up for large-scale production. In addition, this work is intended to provide a means of employing electrochemistry that can be duplicated in most organic chemistry laboratories using readily available glassware and equipment.

  提出了一种从糖基溴化物生产不饱和糖的新方法。这项工作简化了对这些类型物质的现有电化学方法，并可以扩大规模以进行大规模生产。此外，这项工作旨在提供一种使用电化学的方法，可以使用现成的玻璃器皿和设备在大多数有机化学实验室中复制这种方法。
• Variously substituted glycals are readily prepared from glycosyl bromides using (Cp2TiCl)2
  作者：Roxanne P Spencer、Jeffrey Schwartz

  DOI：10.1016/0040-4039(96)00865-9

  日期：1996.6

  Glycosyl halides, variously substituted with ether, acetal, or ester protecting groups, were converted to the corresponding glycals in high yield by reaction with (Cp2TiCl)2. A glycosyl chloride was less reactive than the analogous bromide.

  通过与（C p2 TiCl）2反应，高产率地将被醚，缩醛或酯保护基不同取代的糖基卤化物转化为相应的糖基。糖基氯的反应性低于类似的溴化物。
• Rapid Preparation of Variously Protected Glycals Using Titanium(III)
  作者：Roxanne P. Spencer、Cullen L. Cavallaro、Jeffrey Schwartz

  DOI：10.1021/jo982447k

  日期：1999.5.1

  Glycosyl chlorides and bromides can be rapidly converted to glycals in high yield by reaction with (Cp2Ti[III]Cl)(2). This reagent tolerates a wide range of common carbohydrate protecting groups, including silyl ethers, acetals, and esters; the methodology provides a general route for the preparation of glycals substituted with both acid- and base-labile functionality. A reaction mechanism is proposed that is based on heteroatom abstraction to give an intermediate glycosyl radical. This radical reacts with a second equivalent of Ti(III) to yield a glycosyltitanium(IV) species. P-Heteroatom elimination from the glycosyltitanium(IV) complex gives the glycal.
• Fischer, Susanne; Hamann, Carl Heinz, Journal of Carbohydrate Chemistry, 1995, vol. 14, # 3, p. 327 - 340
  作者：Fischer, Susanne、Hamann, Carl Heinz

  DOI：——

  日期：——