benzyl 2-amino-(R)-4,6-O-benzylidene-2-deoxy-α-D-allopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 2-amino-(R)-4,6-O-benzylidene-2-deoxy-α-D-allopyranoside
• 英文别名: benzyl 2-amino-4,6-O-benzylidene-2-deoxy-α-D-allopyranoside；(2R,4aR,6S,7R,8S,8aS)-7-amino-2-phenyl-6-phenylmethoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-ol
• 化学式: C₂₀H₂₃NO₅
• 分子量: 357.406
• InChiKey: BOSPELTZTUYCQA-FFDFYAMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  83.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  benzyl 2-amino-(R)-4,6-O-benzylidene-2-deoxy-α-D-allopyranoside 在 吡啶 、 sodium hydroxide 、 四丁基溴化铵 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 48.0h， 生成 benzyl 2-amino-(R)-4,6-O-benzylidene-2-deoxy-2-N-3-O-methylidene-2-N-(trans-3-phenyl-2-propenoyl)-α-D-allopyranoside
  参考文献：
  名称：

  Stereoselective synthesis of oxiranes using oxazolidines derived from 2-amino-2-deoxy-d-allose as chiral auxiliaries

  摘要：

  The synthesis of 2,3-epoxyamide derivatives of 2-amino-2-deoxy-D-allose is described. Epoxidation of the corresponding alpha,beta-unsaturated amides with m-CPBA took place with better stereoselectivity when an oxazolidine ring was fused to the 2,3-positions of the sugar molecule. In most cases, both stereoisomers could be isolated and characterized. The stereochemistry of the new stereogenic centers was then determined by cleavage of the,oxirane moiety from the chiral auxiliary, which was also recovered. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00562-6

文献信息

• Tunable Ligands for Asymmetric Catalysis:  Readily Available Carbohydrate-Derived Diarylphosphinites Induce High Selectivity in the Hydrovinylation of Styrene Derivatives
  作者：Haengsoon Park、T. V. RajanBabu

  DOI：10.1021/ja0172013

  日期：2002.2.1

  Only a limited number of ligands have been successfully employed for the Ni-catalyzed asymmetric hydrovinylation reaction. Diarylphosphonites prepared from readily available carbohydrates in conjunction with a highly dissociated counterion ([3,5-(CF3)2-C6H3)4B]- or SbF6-) effect the hydrovinylation of 4-bromostyrene or 4-isobutylstyrene under ambient pressure of ethylene with the best overall selectivities

  只有有限数量的配体已成功用于 Ni 催化的不对称氢乙烯基化反应。由易得的碳水化合物与高度离解的抗衡离子（[3,5-(CF3)2-C6H3)4B]- 或 SbF6-）制备的二芳基亚膦酸酯在乙烯的环境压力下影响 4-溴苯乙烯或 4-异丁基苯乙烯的加氢乙烯基化迄今为止报道的这些重要底物的最佳整体选择性。在 2-芳基丙酸的原型合成中，3-(4-溴苯基)-1-丁烯（以 98% 的分离产率和 89% 的 ee 从 4-溴苯乙烯制备）已被 Ni-转化为 (R)-布洛芬催化与 i-BuMgBr 交叉偶联、臭氧分解和随后生成的醛的氧化。
• Metal-Catalyzed Acyl Transfer Reactions of Enol Esters:  Role of Y₅(O<i>ⁱ</i>Pr)₁₃O and (thd)₂Y(O<i>ⁱ</i>Pr) as Transesterification Catalysts
  作者：Mei-Huey Lin、T. V. RajanBabu

  DOI：10.1021/ol0057131

  日期：2000.4.1

  catalytic amounts (0.05-1 mol %) of Y5(OiPr)13O to give the corresponding esters. In selected cases, the yttrium catalyst promotes the selective O-acylation of amino alcohols without the formation of the amide. Enol esters also react with alpha-amino acid esters in the absence of a catalyst, at room temperature, to give the corresponding amides.

  伯和仲醇在室温下在催化量（0.05-1 mol％）的Y5（OiPr）13O存在下与乙酸乙烯酯或乙酸异丙烯酯反应，得到相应的酯。在某些情况下，钇催化剂可促进氨基醇的选择性O-酰化而不形成酰胺。在没有催化剂的情况下，在室温下，烯醇酯还与α-氨基酸酯反应，得到相应的酰胺。
• Stereoselective synthesis of oxiranes using oxazolidines derived from 2-amino-2-deoxy-d-allose as chiral auxiliaries
  作者：José M. Vega-Pérez、Margarita Vega、Eugenia Blanco、Fernando Iglesias-Guerra

  DOI：10.1016/s0957-4166(01)00562-6

  日期：2001.12

  The synthesis of 2,3-epoxyamide derivatives of 2-amino-2-deoxy-D-allose is described. Epoxidation of the corresponding alpha,beta-unsaturated amides with m-CPBA took place with better stereoselectivity when an oxazolidine ring was fused to the 2,3-positions of the sugar molecule. In most cases, both stereoisomers could be isolated and characterized. The stereochemistry of the new stereogenic centers was then determined by cleavage of the,oxirane moiety from the chiral auxiliary, which was also recovered. (C) 2002 Elsevier Science Ltd. All rights reserved.