(R)-2,3-epoxypropyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside | 321679-22-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: (R)-2,3-epoxypropyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside
• 英文别名: N-[(2R,4aR,6R,7R,8R,8aS)-8-hydroxy-6-[[(2R)-oxiran-2-yl]methoxy]-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl]acetamide
• CAS: 321679-22-5
• 化学式: C₁₈H₂₃NO₇
• 分子量: 365.383
• InChiKey: MVAUQYLDGJMEJJ-DMUYQFPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  98.8
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (R)-2,3-epoxypropyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside 在 sodium azide 、 lithium perchlorate 作用下， 以 乙腈 为溶剂， 以76%的产率得到(R)-3-azido-2-hydroxypropyl 2-acetamido-(R)-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  糖基甘油衍生物作为药物载体系统。环氧烷基N-酰基-β-D-吡喃葡萄糖苷的立体选择性合成及其与亲核试剂的反应

  摘要：

  描述了从 N-乙酰基-D-葡糖胺合成链烯基 2-酰基氨基-4,6-O-benzylidene-2-deoxy-β-D-吡喃葡萄糖苷。用 m-CPBA 氧化烯基糖苷以良好的收率和高立体选择性得到相应的环氧乙烷。可用作药物载体的糖基甘油衍生物的类似物是通过与不同的氮、硫和碳亲核试剂的各种开环反应获得的。

  DOI：

  10.1002/1099-0690(200012)2000:23<3949::aid-ejoc3949>3.0.co;2-j
• 作为产物：
  描述：

  allyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside 在 sodium methylate 、 间氯过氧苯甲酸 、 zinc(II) chloride 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 96.5h， 生成 (R)-2,3-epoxypropyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Stereoselective synthesis of epoxyalkyl glycoside precursors of glycosyl glycerol analogues from alkenyl glycosides of N-acetyl-d-glucosamine derivatives

  摘要：

  The synthesis of epoxyalkyl glycoside derivatives of N-acetyl-D-glucosamine is described. Epoxidation of the corresponding alkenyl glycosides with m-CPBA took place with different stereoselectivity depending on the nature of the unsaturated system and the protecting groups on the sugar moiety. The configuration of the newly formed stereogenic centres has been confirmed unequivocally by chemical correlation. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00649-3

文献信息

• Glycosyl Glycerol Derivatives as Drug Carrier System. Stereoselective Synthesis of EpoxyalkylN-Acyl-β-D-glucopyranosides and Their Reactivity with Nucleophiles
  作者：José M. Vega-Pérez、José I. Candela、Isidora Romero、Eugenia Blanco、Fernando Iglesias-Guerra

  DOI：10.1002/1099-0690(200012)2000:23<3949::aid-ejoc3949>3.0.co;2-j

  日期：2000.12

  The synthesis of alkenyl 2-acylamino-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosides from N-acetyl-D-glucosamine is described. The oxidation of alkenyl glycosides with m-CPBA gives the corresponding oxiranes in good yields, and with high stereoselectivity. Analogues of glycosyl glycerol derivatives, which can be used as drug carriers, were obtained by various ring-opening reactions with different nitrogen

  描述了从 N-乙酰基-D-葡糖胺合成链烯基 2-酰基氨基-4,6-O-benzylidene-2-deoxy-β-D-吡喃葡萄糖苷。用 m-CPBA 氧化烯基糖苷以良好的收率和高立体选择性得到相应的环氧乙烷。可用作药物载体的糖基甘油衍生物的类似物是通过与不同的氮、硫和碳亲核试剂的各种开环反应获得的。
• Stereoselective synthesis of epoxyalkyl glycoside precursors of glycosyl glycerol analogues from alkenyl glycosides of N-acetyl-d-glucosamine derivatives
  作者：José M. Vega-Pérez、José I. Candela、Eugenia Blanco、Fernando Iglesias-Guerra

  DOI：10.1016/s0957-4166(02)00649-3

  日期：2002.11

  The synthesis of epoxyalkyl glycoside derivatives of N-acetyl-D-glucosamine is described. Epoxidation of the corresponding alkenyl glycosides with m-CPBA took place with different stereoselectivity depending on the nature of the unsaturated system and the protecting groups on the sugar moiety. The configuration of the newly formed stereogenic centres has been confirmed unequivocally by chemical correlation. (C) 2002 Elsevier Science Ltd. All rights reserved.